72 Best Wine Hotels in Tuscany

Europe / Italy / Tuscany

72 Best Wine Hotels in Tuscany

Updated in September 2025

Wine hotels in Tuscany

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September 2025

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72 hotels

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1
The Club House

Tuscany (Castelnuovo Berardenga) View map

In the rolling hills of Chianti, we found perhaps one of the best wine hotels in Italy - The Club House. A sanctuary of refined indulgence in the heart of Tuscany’s wine country. With just 15 meticulously designed rooms and suites, this adults-only retreat have panoramic views of vineyards and olive groves that will blow you away. Wine enthusiasts will appreciate the esteemed Vallepicciola Winery, where traditional Tuscan varietals are crafted with modern precision... While for culinary excellence you can choose between two on-site restaurants, where the Michelin-starred blind tasting menu at Il Visibilio stands out. Additional amenities include a panoramic outdoor swimming pool, tennis courts, a golf driving range, and even a holistic spa. You definitely have to go here. Read more

Guest rating: 9.8 (exceptional)

Age limit: 14+ years

Price from: $ 578 /night Set dates

Total price: Check availability
2
Castelfalfi

Tuscany (Castelfalfi) View map

A weekend at Castelfalfi feels like stepping into a Tuscan dream, surrounded by 2,700 acres of vineyards, olive groves, and rolling countryside. The resort’s winery produces outstanding organic wines, and tasting them right where they’re made is of course an unforgettable experience. With five restaurants and bars, every meal here is a highlight - from traditional Tuscan dishes to gourmet fine dining, each paired with wines from the region... The hotel’s 146 rooms and suites are set in a beautifully restored building that was a former tobacco warehouse. How cool is that? Additionally, the on-site Wellness Spa will add another level of relaxation, and for the younger guest there’s even a kids club (which is very rare for a wine hotel!). A must-stay at least once in your life! Read more

Guest rating: 9.7 (exceptional)

Price from: $ 674 /night Set dates

Total price: Check availability
3
Castello Banfi - Il Borgo - Relais et Chateaux

Tuscany (Montalcino) View map

Castello Banfi - Il Borgo is a remarkable winery hotel, set within a historic castle in Tuscany. Known for its world-class wine production, the estate covers over 7,100 acres, with vast vineyards dedicated to cultivating Sangiovese and other grape varieties. The accommodation consists of 14 luxurious suites that blend rustic charm with refined elegance. Guests can take part in exclusive wine tastings, guided tours of the winery, and visits to the on-site balsameria, where premium balsamic vinegar is crafted... Beyond the vineyards, the hotel boasts a fine dining restaurant, an outdoor pool with panoramic views, and a museum dedicated to glass art. The only possible downside to this place is the rather high price, but we definitely think it's worth every penny! Read more

Guest rating: 9.6 (exceptional)

Price from: $ 1,348 /night Set dates

Total price: Check availability
4
Hotel Le Fontanelle

Tuscany (Castelnuovo Berardenga) View map

After a long-awaited escape to Tuscany, Hotel Le Fontanelle genuinely captured our hearts. Hidden in Chianti, the former 13th‑century farmhouse is surrounded by its own vineyards and olive groves as far as the eye can see. Twenty‑five bespoke rooms and suites feature terracotta floors, wood beams, minimal yet warm decor. Many of them open up to lush garden or vine views... Days here began with breakfast on the Belvedere terrace - with fresh pastries, eggs, seasonal fruits - followed by chilled estate Chianti in the hidden cellar. The intimate spa adds Turkish bath and indoor pool comforts, while the on-site Vallepicciola winery invites guided tastings and barrel‑room tours. Everything felt thoughtfully curated yet effortlessly relaxed. We’re already planning our next visit. Read more

Guest rating: 9.5 (exceptional)

Price from: $ 460 /night Set dates

Total price: Check availability
5
Borgo dé Brandi

Tuscany (Monteriggioni) View map

Set on the hills just outside Monteriggioni, Borgo dé Brandi is a restored medieval hamlet turned boutique retreat. The estate looks out across olive groves and Chianti vines, with Monteriggioni’s iconic fortress rising in the distance like something from a postcard. Suites here are spacious and beautifully simple, blending stone walls and beamed ceilings with understated elegance. The property also has a pool with panoramic views - the kind of spot that makes you want to linger all afternoon... In our opinion, it's the balance that makes Borgo dé Brandi so special: peaceful countryside, wonderful hospitality, and wines from one of Italy’s most famous regions. No wonder it’s often described as one of the best winery accommodations in Tuscany! Read more

Guest rating: 9.3 (superb)

Price from: $ 194 /night Set dates

Total price: Check availability
6
Il Borro Relais & Châteaux

Tuscany (San Giustino Valdarno) View map

Ever since we first discovered Il Borro Relais & Châteaux, we had been itching to experience its legendary Tuscan charm - and when it finally happened it didn’t disappoint. Set in a lovingly restored medieval village owned by the Ferragamo family, the place radiates authenticity, blending organic vineyards, olive groves, and centuries-old farm buildings. Accommodations range from intimate suites in the medieval core to spacious villas like Villa Casetta, most with sweeping views of the landscapes... But the best part (if you ask us) was the wine tour that passed through organic Sangiovese, Merlot, and Cabernet vines, guided by passionate experts who bring every barrel and bottle to life. Additional highlights include spa indulgence in a state-of-the-art wellness centre, vineyard hikes, horseback riding, and cooking classes. What are you waiting for? Book now! Read more

Guest rating: 9.3 (superb)

Price from: $ 596 /night Set dates

Total price: Check availability
7
Rosewood Castiglion del Bosco

Tuscany (Castiglione del Bosco) View map

Perched in Tuscany's enchanting Val d'Orcia, Rosewood Castiglion del Bosco is a 5,000-acre estate offering lucky guests an immersive wine journey. As one of the historic producers of Brunello di Montalcino, the on-site winery crafts exceptional wines that reflect the region's rich heritage. The hotel's absolutely incredible accommodations include 42 suites, exuding authenticity with luxurious features and antique furnishings... Alongside it also have 11 outstanding villas, transformed from 17th- and 18th-century farmhouses, each featuring heated private pools, terraces, and gardens! This unique blend of history, luxury, and culture makes this a must-visit destination in Italy for wine enthusiasts and travellers seeking nothing but the best. Read more

Guest rating: 9.2 (superb)

Price from: $ 3,499 /night Set dates

Total price: Check availability
8
Precise Tale Poggio Alla Sala

Tuscany (Montepulciano) View map

When it comes to luxury wine hotels in Tuscany, Precise Tale Poggio Alla Sala stands out with its fusion of historic charm and contemporary flair. Set in a spectacular 18th-century villa framed by olive groves and vineyards, its 60 suites and rooms feature vaulted frescoed ceilings, terracotta floors, and private terraces. A stay here includes globe-inspired dining where Tuscan classics meet subtle Eastern spices, paired with estate and regional wines... Relaxation flows from four pools, spanning from indoor, adults-only and family-friendly options. I also offers hammams and massage treatments. Added touches include their vaulted wine cellar for tastings, cultural design nods to the Silk Road, and word-class service - making this one of our absolute favourites hotels in Montepulciano. Read more

Guest rating: 9.1 (superb)

Price from: $ 453 /night Set dates

Total price: Check availability
9
COMO Castello Del Nero

Tuscany (Tavarnelle in Val di Pesa) View map

In the world-famous Chianti wine area, we stumbled upon the extraordinary 5-star COMO Castello Del Nero. A stunning hotel set in a 12th-century castle - offering a refined escape, surrounded by rolling vineyards and olive groves. Their on-site winery produce some exceptional wines, with Sangiovese, Cabernet Sauvignon, and Merlot thriving in the rich soil... And as a hotel guest you can enjoy everything! From exclusive tastings, exploring the historic wine cellar, and fine dining at the Michelin-starred La Torre, where seasonal flavours are cooked to perfection. Also - the spa, infused with COMO’s wellness philosophy, provides a fantastic sanctuary of pure relaxation. We absolutely love this place. Read more

Guest rating: 9.0 (superb)

Price from: $ 1,742 /night Set dates

Total price: Check availability
10
Relais Villa Olmo

Tuscany (Impruneta) View map

Rising above the famous Chianti Valley, we found Relais Villa Olmo. A captivating wine-and-food hideaway built in a charming 16th-century villa. With fewer than 20 rooms - including some very luxurious villas with private pools - each space showcases terracotta floors, handcrafted furnishings, and sweeping vineyard views. The heart of the experience lies in its Diadema wines, produced and aged on site in oak barrels and terracotta amphorae... Wine lovers will relish guided tastings in the historic cellar and the hands-on Wine Lab, where you can create your own blend! So whether you're looking forward to unwind by the pool, explore the surroundings with a Vespa, or toast fine wines in ancient stone rooms, we are pretty sure you'll love every moment here. Read more

Guest rating: 9.0 (superb)

Price from: $ 359 /night Set dates

Total price: Check availability
11
L'Andana Tenuta La Badiola

Tuscany (Castiglione della Pescaia) View map

L'Andana Tenuta La Badiola is a destination where fine winemaking and Tuscan heritage come together. Located in the Maremma region near Castiglione della Pescaia, this 5-star hotel is surrounded by the striking beauty of vineyards as far as the eye can see. The on-site winery offers guided tours and tastings, showcasing wines crafted from regional grape varieties. Guests can visit the wine shop to sample and take home bottles of Acquagiusta - known for its balanced flavours... Dining is another highlight, with Michelin-starred La Trattoria Enrico Bartolini serving refined dishes that - of course - are complemented by selections from the winery. Beyond wine and food, L'Andana provides a collection of 56 elegant rooms, a spa, and various activities, all designed to create a complete Tuscan experience. Read more

Guest rating: 8.7 (fabulous)

Price from: $ 571 /night Set dates

Total price: Check availability
12
Castello di Velona Resort, Thermal SPA & Winery

Tuscany (Montalcino) View map

Experience the true essence of Tuscany at Castello di Velona Resort. Set within the walls of a historic castle overlooking the Val d’Orcia, this exceptional estate is surrounded by olive groves and vineyards that produce outstanding Brunello di Montalcino wines. Here, guests can savour these vintages where they are crafted, dine on Tuscan specialities that celebrate the region’s rich traditions, and unwind in the natural thermal waters of the world-class spa... With elegant suites, breathtaking views and a setting steeped in history, every moment at Castello di Velona promises a true taste of Tuscan luxury. Read more

Guest rating: 8.4 (very good)

Price from: $ 979 /night Set dates

Total price: Check availability
13
Borgo Argiano

Tuscany (Castelnuovo Berardenga) View map

Strategically located in the hills just south of Siena, Borgo Argiano offers a quiet and luxurious base from which to explore the heart of Tuscany. Embedded in vineyards, olive groves, and cypress-lined lanes, this beautifully restored estate is full of both rustic charm and modern comfort. The apartments and suites are airy and understated, many with private terraces that open to wide views of the countryside... It’s an adults-only property, which adds to the peaceful atmosphere - perfect for long, relaxed breakfasts, afternoons by the pool, or a quiet glass of Chianti Classico as the sun begins to fade behind the hills. Read more

Guest rating: 9.9 (exceptional)

Age limit: 15+ years

Price from: $ 399 /night Set dates

Total price: Check availability
14
Abbadia Wine Relais

Tuscany (Montefollonico) View map

Some places don’t shout for attention - they win you over with quiet beauty, deep roots, and a glass of something remarkable. Abbadia Wine Relais is one of them. Set in the gently rolling hills of Tuscany, this boutique wine stay is built around an 18th-century farmhouse surrounded by the vineyards of the historic Tenuta di Angoris. The atmosphere is peaceful, elegant, and unpretentious. Just twelve rooms, each tastefully renovated with exposed beams, warm wood, and soft natural light... It feels more like staying in a private home than a hotel - and that's exactly the point. Read more

Guest rating: 9.8 (exceptional)

Age limit: 18+ years

Price from: $ 288 /night Set dates

Total price: Check availability
15
Borgo Del Cabreo

Tuscany (Greve in Chianti) View map

Perched in the rolling hills of Greve in Chianti, Borgo Del Cabreo is one of those places that effortlessly combines Tuscan elegance with the spirit of wine. Owned by the Folonari family, whose name is woven into Italy’s winemaking history, the estate is surrounded by vineyards producing some of Chianti Classico’s most celebrated labels... The accommodation is refined yet intimate - restored stone farmhouses transformed into stylish suites with sweeping countryside views, infinity-edge pools, and terraces perfect for sipping a glass of their Riserva at sunset. Mornings begin with generous breakfasts made from local produce, and afternoons can mean wine tastings in the estate’s historic cellars or quiet walks among cypress-lined paths. It’s an ideal base for wine lovers who want both sophistication and authenticity, where every detail - from the architecture to the glass in your hand - reminds you that this is Tuscany at its most timeless. Read more

Guest rating: 9.8 (exceptional)

Price from: $ 379 /night Set dates

Total price: Check availability
16
Castel Brunello

Tuscany (Montalcino) View map

The magical Castel Brunello is a restored stone hideaway perched just beyond the walls of Sant’Angelo in Colle. Overlooking Brunello’s vine-strewn hillsides, this isn’t your typical hotel - it’s a cluster of rustic-chic apartments that feel more like a Tuscan home than a tourist spot. Each apartment is gracefully spacious, with wood-beamed ceilings, terracotta floors, fully equipped kitchens, and terraces that open to vineyard views. Perfect for couples, families, or groups who love independence without losing authenticity... Castel Brunello really offers a peaceful base for exploring Montalcino’s vineyards and medieval charm. Read more

Guest rating: 9.7 (exceptional)

Price from: $ 445 /night Set dates

Total price: Check availability
17
Castello La Leccia

Tuscany (Castellina in Chianti) View map

We had read so many great reviews about Castello La Leccia, which meant we had very high expectations before we arrived. And after a couple of days here we must say it delivered an experience even more special than we imagined. Set high in the Chianti hills, this beautiful adults-only (14+) hotel is built in a restored medieval castle. It is surrounded by vineyards, olive groves and woodland, offering panoramic views at every turn. What made our stay here so memorable was the perfect balance of history and contemporary comfort... Days here were spent exploring the estate’s organic winery, enjoying tastings of its exceptional Chianti Classico, and feast on regional dishes crafted from local ingredients. From the peaceful gardens to the inviting pool overlooking the vineyards, every detail felt well thought out and we left already dreaming of our return. Read more

Guest rating: 9.7 (exceptional)

Age limit: 14+ years

Price from: $ 337 /night Set dates

Total price: Check availability
18
Podere Campriano Winery

Tuscany (Greve in Chianti) View map

If you love discovering hidden gems you're in for a treat! Because Podere Campriano Winery delivers a one of a kind experience paired with intimate Chianti Classico moments in Chianti. Offering a family-run, four-generation organic vineyard spans 3 hectares of Sangiovese vines and olives. Their Chianti Classico DOCG and Riserva are crafted in historic cellars, and tastings often begin right in the vines - paired with Mosto Cotto and olive oil from the estate... The accommodations come in spacious suites and apartments that open up to vine-filled views, parquet floors, and modern touches like full kitchens and salt-water pools. We also love the warm hospitality from the hosts Elena and Luca, the superb breakfasts, enchanting cooking classes, and peaceful evenings by the pool with a glass in hand. Read more

Guest rating: 9.6 (exceptional)

Age limit: 18+ years

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Total price: Check availability
19
Agriturismo La Sovana

Tuscany (Sarteano) View map

Southern Tuscany, near the border with Umbria, produces some of Italy’s most characterful wines thanks to its mix of rolling hills, sunny climate, and centuries-old winemaking traditions. Agriturismo La Sovana puts you right in the middle of it all. Set on a family-run estate between Montepulciano and Chiusi, it’s surrounded by vineyards, olive groves, and cypress-lined lanes. Guests can taste the estate’s own vintages, stroll the vines at golden hour, or join a wine-paired dinner featuring local specialties... Rooms and apartments blend rustic Tuscan charm with modern comfort, there’s a pool with countryside views, and the staff treat you like an old friend. We know you'll love this place! Read more

Guest rating: 9.5 (exceptional)

Price from: $ 262 /night Set dates

Total price: Check availability
20
Borgo Macereto

Tuscany (Dicomano) View map

In the rolling Tuscan hills we found the gorgeous Borgo Macereto. Built in a restored medieval hamlet that sits right in the Chianti Classico area, surrounded by vineyards that have been cultivated for centuries. The estate is alive with the rhythms of winegrowing - from the first pruning in winter to the harvest in autumn - and guests are invited to be part of it through tastings, tours, and leisurely walks through the vines... We also need to mention the on-site restaurant that celebrates Tuscan cuisine at its purest, always paired with wines from the estate. Borgo Macereto truly offers a wine stay that feels both rooted in the past and very much alive in the present. Read more

Guest rating: 9.5 (exceptional)

Price from: $ 148 /night Set dates

Total price: Check availability
21
Borgo Pignano Tuscany

Tuscany (Pignano) View map

Borgo Pignano has so many special features that it's a gamble of which comes to mind first. Set on a 750-acre organic estate between Volterra and San Gimignano, it consists of an elegantly restored 18th-century villa, surrounded by olive groves, vineyards, and sweeping views of the rolling countryside. Rooms and suites are thoughtfully appointed, blending period details with understated luxury. There are also stand-alone farmhouses and maisonettes for those seeking extra privacy... The estate produces its own olive oil, wine, honey, and herbs - all of which find their way into the excellent cuisine served at the two on-site restaurants. Guests can also join cooking classes, explore forest trails on horseback, unwind at the wellness centre, or simply relax by the limestone infinity pool overlooking the hills. It’s a place that invites you to slow down, breathe, and enjoy the quiet beauty of Tuscany at its most timeless. Read more

Guest rating: 9.5 (exceptional)

Price from: $ 975 /night Set dates

Total price: Check availability
22
Borgo San Felice

Tuscany (Castelnuovo Berardenga) View map

Surrounded by its very own vineyard and set within a medieval hamlet, Borgo San Felice has firmly earned its reputation as one of Tuscany’s most compelling wine retreats. The on-site winery produces celebrated Chianti Classico - with tours weaving through ancient cellars into sunlit barrel rooms. Over 60 rooms and suites live across original stone buildings - each unique and full of character. Wellness highlights include a spa offering grape‑must(!) treatments and a heated outdoor pool overlooking the vines... Our stay here felt almost cinematic - sunset sips by the pool, fun cooking classes in the vegetable garden, and endless bottles of Vigorello as twilight draped across the Chianti hills. We are already looking forward to our return. Read more

Guest rating: 9.5 (exceptional)

Price from: $ 790 /night Set dates

Total price: Check availability
23
Poggio Piglia

Tuscany (Chiusi) View map

Poggio Piglia provides a perfect base for exploring the rich history and culture of Tuscany, with lots of nearby attractions and the wine regions of Montepulciano and Montalcino. Set atop a serene hill near Chiusi, this Tuscan boutique hotel offers modern design and traditional charm in its 9 spacious suites. The estate spans 19 hectares of vineyards, olive groves, and woodlands. Guests can enjoy culinary delights at the on-site restaurant, the historic wine cellar, and the lovely infinity pool that overlooks the rolling hills.

Guest rating: 9.5 (exceptional)

Price from: $ 292 /night Set dates

Total price: Check availability
24
Villa Poggiano

Tuscany (Montepulciano) View map

If Tuscan dreams had a postcard, it might look a lot like Villa Poggiano. Cypress-lined driveways, sun-dappled courtyards, and cinematic views over Montepulciano’s rolling hills. This 18th-century villa is pure old-world glamour, but without the stuffiness: think frescoed ceilings, antique furniture, and a saltwater pool that begs for a languid afternoon float. Mornings kick off with breakfast on the terrace - with locally baked pastries, creamy ricotta, and delicious cappuccinos... The staff know every secret wine bar and family-run trattoria within a cork’s throw, and they’ll happily set you up for a day of Brunello tastings or hilltown hopping. Villa Poggiano is where you go when you want Tuscany at its best - lush landscapes, history at every turn, and that “I could stay forever” feeling that hits before you’ve even unpacked. Read more

Guest rating: 9.5 (exceptional)

Age limit: 18+ years

Price from: $ 315 /night Set dates

Total price: Check availability
25
Wine Resort Conti di San Bonifacio

Tuscany (Montemassi) View map

Our stay at this Tuscan winery hotel was magical! The vineyard views, golden sunsets, and charming countryside were pure poetry. The estate's wines — rich, earthy reds with notes of cherry and leather were a joy to taste (and bring home!). Our gorgeous room had timeless Tuscan character with personalized touches. If you seek an authentic, indulgent Italian escape, this is a must!

Guest rating: 9.5 (exceptional)

Price from: $ 804 /night Set dates

Total price: Check availability
26
Wine Resort Dievole

Tuscany (Vagliagli) View map

Tuscany is home to more winery hotels than almost any other region in Italy, and many of them sit right on estates producing world-famous Chianti Classico. Wine Resort Dievole is one of those rare places where the postcard views, the wine in your glass, and the history under your feet all line up perfectly. Just outside Siena, this centuries-old estate unfolds over rolling hills of vines and olive groves... Guests can taste Dievole’s elegant Chianti Classico and extra virgin olive oil at the source, join vineyard walks, or simply claim a spot under the cypress trees with a glass in hand. Rooms and suites mix rustic Tuscan charm with refined touches, and the infinity pool frames views so wide you almost forget to swim. It’s the kind of place where wine isn’t just part of the stay - it is the stay. Read more

Guest rating: 9.5 (exceptional)

Age limit: 18+ years

Price from: $ 432 /night Set dates

Total price: Check availability
27
Hotel Belvedere Di San Leonino

Tuscany (Castellina in Chianti) View map

Did you know Tuscany is home to more than 57 DOC and DOCG wines, making it one of the most celebrated wine regions in the world? Right in the heart of this landscape sits Hotel Belvedere Di San Leonino. Once an old farmhouse, it has been transformed into a charming boutique hotel where the history of Tuscan winemaking is never far from sight. Rooms are rustic and welcoming, with terracotta floors, wooden beams, and views that stretch over rolling vineyards and olive groves... The restaurant leans into local traditions - hearty Tuscan dishes paired with bottles of Chianti that taste even better when enjoyed on the terrace at sunset. Add a pool overlooking the vines, and you’ve got the ultimate mix of relaxation and wine immersion. Read more

Guest rating: 9.4 (superb)

Price from: $ 192 /night Set dates

Total price: Check availability
28
Locanda Le Piazze

Tuscany (Castellina in Chianti) View map

The exceptional Locanda Le Piazze is a small, luxurious, boutique hotel a short drive from Castellina in Chianti. Once a 16th-century farmhouse, it nowadays offers wine lovers a chance to stay in the middle of rows of Sangiovese vines and views that stretch endlessly across the Tuscan countryside. Inside, the style is understated and elegant - crisp linens, warm tones, and thoughtful touches that make the rooms both comfortable and refined. The highlight, though, is the food and wine... The Michelin-recommended restaurant celebrates Tuscan flavours with a modern twist, each dish paired beautifully with local Chianti Classico wines. Spend your afternoons by the infinity pool gazing at the vineyards, or take a walk through the rolling hills before returning for a long dinner under the stars. This is Chianti living at its most enchanting. Read more

Guest rating: 9.4 (superb)

Age limit: 14+ years

Price from: $ 319 /night Set dates

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29
Tenuta Pianirossi

Tuscany (Cinigiano) View map

If wandering through vineyards and uncorking wine where it’s made feels like your kind of getaway, Tenuta Pianirossi is a dream come true. Nestled in Tuscany’s Maremma, this organic winery turned relais radiates rustic charm, handcrafted suites, and views that stretch into softly rolling hills. What’s remarkable is the passion that goes into every bottle: 14 hectares of vines are tended by hand, and the produces are crafted with sustainability at heart. Here, wine isn’t just a detail - it’s woven into the rhythm of life... Days begin with breakfast made from local products, and you’ll likely find yourself poolside with a glass of estate-grown wine, gazing across the infinity edge toward the vineyard panorama. Ideal for couples, small families, or anyone craving a comfort and wine passion - all wrapped up in one unforgettable stay. Read more

Guest rating: 9.4 (superb)

Price from: $ 177 /night Set dates

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30
Torre a Cona Wine Estate

Tuscany (Florence) View map

Discover living history at Torre a Cona Wine Estate, an 18th-century villa just outside Florence that has been transformed into a boutique haven for wine and culture lovers. The estate’s rooms and suites blend antique charm with understated luxury - frescoed ceilings, terracotta floors, and windows that open onto rolling vineyards and olive groves. Every corner reminds you that this was once a noble residence, now reimagined for modern travellers seeking beauty and authenticity... Lucky guests staying here can taste estate-made Chianti Colli Fiorentini and elegant single-vineyard wines right where they’re produced. Add to that seasonal Tuscan cuisine served with estate pairings, and it becomes the kind of stay where history, hospitality, and wine seamlessly come together. Read more

Guest rating: 9.4 (superb)

Price from: $ 509 /night Set dates

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31
Viticcio

Tuscany (Greve in Chianti) View map

Just 1.5 km from Greve in Chianti we found the amazing Viticcio where guests can stroll through picturesque vineyards and enjoy the breathtaking landscapes. The estate boasts meticulously restored farmhouse apartments, each featuring private entrances, outdoor spaces, and access to a serene saltwater pool amidst lush olive groves. Viticcio's commitment to organic viticulture shines in their Chianti Classico wines, celebrated for capturing the essence of the Tuscan terroir... Engage in immersive wine tours and tastings, delving into the art of winemaking and savouring the hotel's exceptional offerings. Don't hesitate to book this place! Read more

Guest rating: 9.4 (superb)

Price from: $ 178 /night Set dates

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32
Wine Estate Rooms Paradiso di Cacuci

Tuscany (Montalcino) View map

Wine Estate Rooms Paradiso di Cacuci is exactly what its name promises - a little slice of paradise for wine lovers. This family-run estate gives you the rare chance to wake up surrounded by vines that produce some of Piedmont’s most celebrated reds. The guest rooms are bright, contemporary, and designed with vineyard views in mind - the kind of outlook that tempts you to linger over morning coffee. But the real highlight is the winery itself... Guests are welcomed into the cellar to taste Barolo, Barbera, and Dolcetto right where they’re made, guided by people who live and breathe these wines. Add to that a terrace perfect for sipping a glass at sunset and you’ve got one of those quietly special spots in the Langhe. Read more

Guest rating: 9.4 (superb)

Price from: $ 257 /night Set dates

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33
Wine Resort Colsereno

Tuscany (Montalcino) View map

Tucked into Montalcino’s countryside, Wine Resort Colsereno is a family-owned property dating back to the late 1800s. It spans 70 hectare, with 6 of them dedicated to Brunello vineyards. Meaning those bold Sangiovese vines are literally in your backyard. Accommodation comes in three spacious and well‑equipped apartments. Guests staying here can enjoy visits to the on‑site winery and tasting room where you can sip fresh cru straight from the barrel!.. Lazy afternoons drift by the seasonal pool or cycling through vine rows. With cooking classes, bike tours, and a blend of relaxed elegance and vineyard authenticity, Colsereno delivers an intimate escape that’s as charming as it is memorable. Read more

Guest rating: 9.4 (superb)

Price from: $ 270 /night Set dates

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34
Agriturismo Casale Dello Sparviero

Tuscany (Castellina in Chianti) View map

Casale dello Sparviero occupies a beautifully restored former monastery in Castellina in Chianti, set within 380 hectares of land - 90 of them devoted to organic Sangiovese vineyards. Six warm, well-appointed apartments with kitchens and terracotta floors overlook vine-draped hills, creating a truly homely yet tranquil atmosphere. The estate crafts Chianti Classico DOCG, Superiore and IGT wines, with daily tastings in the garden or cellar - including complimentary evening sessions under cypress trees at sunset... Hiking the vineyard trails, lingering by the infinity pool, or sipping on a bottle of house wine on your terrace - what more can you ask for? Read more

Guest rating: 9.3 (superb)

Price from: $ 153 /night Set dates

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35
Agriturismo Podere San Gregorio

Tuscany (Pienza) View map

Just a few steps from the medieval streets of Pienza, Agriturismo Podere San Gregorio offers that perfect mix of Tuscan authenticity and vineyard charm. This family-run farmhouse looks out over rolling hills, olive groves, and Sangiovese vines destined to become Vino Nobile di Montepulciano - a wine with as much character as the land itself. The rooms are rustic yet comfortable, with stone walls, wooden beams, and plenty of warmth that makes you feel instantly at home. Outside, the estate opens onto wide views of the Val d’Orcia... Guests can sample the family’s wines and olive oil, explore the vineyards, or wander into town for pecorino cheese and handmade pasta. It's relaxed, genuine and full of Italian hospitality. For us, that’s what makes Podere San Gregorio so unforgettable. Read more

Guest rating: 9.3 (superb)

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36
Castello Di Vicarello

Tuscany (Sasso dʼOmbrone) View map

Hidden in the heart of Tuscany's Maremma, Castello di Vicarello is the kind of wine retreat that feels like discovering a secret masterpiece. The 13th‑century castle has been lovingly restored by the Baccheschi‑Berti family and is set amid 40 hectares of organic vineyards, olive groves, and gardens. Ten individually‑styled suites - ranging from medieval tower quarters to modern spa-designed spaces - showcase vaulted ceilings, fireplaces, and private terraces overlooking the vine‑rich land... A standout is the Spa Suite, complete with its own sauna and wine-barel(!) hot tub. The castle’s organic vineyards use ancient high-density planting techniques - a passion project led by Brando Baccheschi‑Berti. Tastings begin among the vines, move into historic cellars, and continue over candlelit dinners crafted from estate-grown produce. Other things worth mentioning is the hotel's two infinity pools, the fantastic hiking and biking trails that weave through the property, and lovely cooking classes which give hands-on flair to the stay. Read more

Guest rating: 9.3 (superb)

Price from: $ 1,707 /night Set dates

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37
Fattoria di Cinciano

Tuscany (Poggibonsi) View map

Did you know that Chianti Classico has been produced for nearly 800 years, with strict rules protecting its authenticity? At Fattoria di Cinciano, you can experience that tradition firsthand on an estate that traces its history back to the 12th century. Perched between Siena and Florence, this former medieval hamlet is now a working wine estate and agriturismo, surrounded by vineyards and olive groves... Guests are invited to explore the cellars, taste Chianti Classico and Super Tuscan blends, and learn how the land has shaped winemaking here for centuries. The accommodations keep the spirit of Tuscany alive – rustic yet elegant rooms and apartments with terracotta floors, wooden beams, and sweeping countryside views. Between vineyard tours, poolside afternoons, and meals at the on-site restaurant, you'll start to plan your return before you've even checked-out. Read more

Guest rating: 9.3 (superb)

Price from: $ 217 /night Set dates

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38
Pensieri di Cavatina

Tuscany (Castelnuovo Berardenga) View map

In the hills of Chianti (just 15 minutes from Siena) we found the wonderful Pensieri di Cavatina. Built in a thoughtfully restored 17th-century estate it is surrounded by organic vineyards and olive groves. The stylish boutique accommodations feature elegantly furnished rooms with panoramic views, some also with private terraces. And the on-site restaurant presents Tuscan cuisine with a modern twist, complemented by wines produced from the estate's own vineyards... Guests can also partake in wine tastings, cooking classes, and wellness activities. Don't hesitate to book this place if you find availability! Read more

Guest rating: 9.3 (superb)

Price from: $ 244 /night Set dates

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39
Relais Casanova

Tuscany (San Gusmè) View map

Some stays in Tuscany are about history, others about wine - Relais Casanova is thankfully about both. Set just outside San Casciano dei Bagni, this countryside escape gives you space, quiet, and those rolling postcard views that seem to stretch on forever. The rooms and suites are spread across charming villas, blending terracotta floors and wood-beamed ceilings with a refined touch of comfort... The spa is a highlight, fed by the same thermal waters that have made this area famous since Roman times, while the outdoor pool is all about lazy afternoons and the possibility to take a refreshing dip. It’s a place for romance, relaxation, and long evenings spent watching the hills turn golden. Read more

Guest rating: 9.3 (superb)

Price from: $ 220 /night Set dates

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40
Salcheto WineHouse

Tuscany (Montepulciano) View map

On a recent wine trip through Montepulciano we discovered Salcheto WineHouse, a forward-thinking winery that’s rewriting the rules of Tuscan hospitality. Known for its commitment to sustainability, Salcheto produces organic, off-grid wines powered entirely by renewable energy - and you get to taste them just steps from the cellar where they’re born. You can stay in one of their 6 stylishly simple rooms, each designed with natural materials and big windows looking out over the vines and rolling countryside... Breakfast is all about local, seasonal produce, and the on-site restaurant serves creative takes on traditional Tuscan dishes, paired of course with Salcheto’s acclaimed Vino Nobile. Between winery tours, lounging by the pool, or simply sipping a glass, this is the kind of place that makes you want to stay longer than planned. One of Tuscany’s most exciting winery accommodations. Read more

Guest rating: 9.3 (superb)

Price from: $ 182 /night Set dates

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41
Salvadonica

Tuscany (San Casciano in Val di Pesa) View map

You know those dreamy Tuscan images? Winding roads, cypress trees, and rows of vines stretching into the horizon... Salvadonica is basically the real-life version - only better. Because you get to sleep there. This boutique wine estate isn’t about over-the-top luxury. It’s about atmosphere, charm, and a slow pace that pairs perfectly with a glass of Chianti Classico - made just outside your door. The guest rooms are both luxurious and rustic in the same time, featuring terracotta floors, wooden beams and countryside views... The hotel's pool sits right above the vineyards, and yes, sunset swims with a glass in hand are practically mandatory. Add in a restaurant that turns out Tuscan classics like wild boar ragù (paired with estate wines, naturally), and you’ve got yourself a getaway that’s equal parts authentic and indulgent. Read more

Guest rating: 9.3 (superb)

Price from: $ 330 /night Set dates

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42
Villa S.Andrea

Tuscany (San Casciano in Val di Pesa) View map

There are so many things we love about Villa S. Andrea that we don't know where to start. Perhaps with its breathtaking location? Nestled just minutes from Florence, in the heart of Chianti’s famed wine region. Our stay in this charming farmhouse was like living in a postcard where ancient stone walls enveloped us as we strolled past vine rows and olive groves... The vineyard itself, sprawling 1,500-acres, is quietly impressive, producing Chianti Classico, barrel-aged Riserva, and even Vin Santo, all made with meticulous craftsmanship. We joined a tasting in the rustic cellar and left with a newfound appreciation for Tuscany’s traditional methods. In addition, the hotel also offers two pools, cooking classes, bike rides through the countryside, and an exceptional on-site restaurant. Read more

Guest rating: 9.3 (superb)

Price from: $ 248 /night Set dates

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43
Agriturismo Cesani

Tuscany (San Gimignano) View map

If you’ve ever wanted to live your best rustic Italian fantasy - with a glass of white in hand, vineyard views, and not a care in the world. Agriturismo Cesani is calling your name. Perched in the hills just outside San Gimignano, this family-run gem blends warm hospitality, jaw-dropping scenery, and a whole lot of seriously good wine... The Cesani family has been producing organic Chianti wines here for generations - and yes, you get to taste it all (along with olive oil and snacks) in their rustic cellar that almost makes you want to move in. Between lounging by the pool, enjoying homemade cakes at breakfast, and watching the sun set, you'll wonder why you ever bothered with a regular hotel. Cheers! Read more

Guest rating: 9.2 (superb)

Price from: $ 136 /night Set dates

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44
Agriturismo Tra gli Ulivi, Chiappini Winery

Tuscany (Bolgheri) View map

Located in wonderful settings where some of Italy’s most celebrated Super Tuscan wines are born, Agriturismo Tra gli Ulivi offers guests the chance to stay among the vines. The Chiappini family has been producing organic wines here for decades, with labels like Guado de’ Gemoli earning international acclaim - and you can taste them right where they’re crafted. Accommodations are warm and authentic, spread across farmhouse-style apartments surrounded by vineyards and olive groves... This isn’t a glossy resort but rather a genuine winery stay, where mornings begin with birdsong and evenings end with a glass of Chiappini’s Bolgheri Rosso as the sun dips behind the cypress trees. Read more

Guest rating: 9.2 (superb)

Price from: $ 324 /night Set dates

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45
Borgo Vescine

Tuscany (Radda in Chianti) View map

What makes Borgo Vescine so special? Well, think of it as Chianti Classico’s greatest hits wrapped into one stay: rolling vineyards, medieval stone walls, and glasses of ruby-red that seem to taste better with every sunset. This former 13th-century hamlet has been reimagined as a boutique hotel, but it hasn’t lost its soul - cobbled lanes still wind between buildings, and the hills still steal your attention at breakfast. The wine is the star here, of course... You can taste Vescine’s own Chianti Classico just metres from where the grapes grow, then wander through the vines with a glass in hand. Rooms hit that sweet spot between rustic charm and modern ease, and the pool has a view worth writing home about. In short, Borgo Vescine nails the Tuscan fantasy without feeling like it’s trying too hard. Read more

Guest rating: 9.2 (superb)

Price from: $ 450 /night Set dates

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46
Relais Del Lago

Tuscany (Capannori) View map

Never heard of Relais Del Lagon? Don’t worry, neither had we until recently - but wow, this little gem in Tuscany deserves to be on every wine lover’s radar. Think rolling vineyards stretching to the horizon, cypress-lined lanes, and that golden Tuscan light that makes you feel like you’ve stepped inside a painting. The relais is intimate and stylish, more boutique hideaway than big resort, with beautifully curated rooms that mix rustic stone walls with modern touches... And then there’s the wine - the estate produces its own, so you’re not just sipping Chianti; you’re sipping their Chianti, poured a few steps from where the grapes were grown. Perfect for couples, dreamers, and anyone who thinks a holiday isn’t complete without a vineyard at the doorstep. Read more

Guest rating: 9.2 (superb)

Price from: $ 136 /night Set dates

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47
Terre di Baccio

Tuscany (Greve in Chianti) View map

Just wow! The outstanding Terre di Baccio is the kind of Chianti winery hotel that makes you want to pinch yourself. Set in the heart of the region’s vine-covered hills, this working estate surrounds you with rows of Sangiovese grapes, olive groves, and the scent of freshly turned earth. As a guest you can enjoy vineyard walks right outside your door and tastings in a beautifully restored chapel, where their Chianti Classico tells the story of the land in every sip... Meals are a love letter to the estate-organic produce from the gardens, local specialties, and, of course, their own wines. Add to that a pool overlooking the hills, warm, personal service, and that feeling of being woven into vineyard life, Terre di Baccio is pure Tuscan magic. Read more

Guest rating: 9.2 (superb)

Price from: $ 313 /night Set dates

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48
Agriturismo Oliviera Winery & Hiking

Tuscany (Vagliagli) View map

Have you ever dreamed of waking up amidst the vineyards of Chianti, with the aroma of wine and olive groves in the air? At Agriturismo Oliviera Winery, that dream becomes reality. This charming agriturismo offers guests an authentic Tuscan experience, combining comfortable accommodations with unforgettable wine (and olive) experiences! During your stay, you can explore the on-site vineyards and winery, gaining insight into the production of their esteemed Chianti wines and olive oil... And daily tastings allow you to try these products firsthand. For those seeking adventure, the surrounding Chianti hills provide ample opportunities for hiking, horseback riding, and cycling - making it the perfect hotel for an Italian getaway! Read more

Guest rating: 9.1 (superb)

Price from: $ 136 /night Set dates

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49
Borgo Scopeto Wine & Country Relais

Tuscany (Vagliagli) View map

Set in the Chianti hills near Siena, this beautifully restored medieval hamlet is surrounded by vineyards that produce their own Chianti Classico and Riserva wines. The atmosphere is pure Tuscan elegance-historic stone buildings, cypress-lined paths, and views that stretch for miles. The estate offers wine tastings, a spa using grape- and olive-based products, and two restaurants where local cuisine is paired with their wines. It’s a working winery, a luxurious boutique retreat, and a slice of Tuscan life all in one... It’s the perfect place to slow down, sip something local, and watch the sun set over the vines. Read more

Guest rating: 9.1 (superb)

Price from: $ 444 /night Set dates

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50
Borgo Syrah

Tuscany (Cortona) View map

If your idea of a wine getaway includes Tuscan hills, modern design, and estate-grown Syrah, Borgo Syrah in Cortona checks every box. Set on Tenimenti d’Alessandro’s estate - a winery renowned for its Cortona Syrah wines - this restored village feels like a stylish retreat rooted in the rhythm of the vineyard. The hotel's villas and apartments are converted from historic olive-presses and barns, each subtly luxurious with fully equipped kitchens, open living spaces, and private patios overlooking vine-draped hills... Relaxation continues at the spa and wellness area, where emotional showers, sauna, and a pool merge into a soul-nourishing experience. Guests can also enjoy walks through the vineyards and unforgettable wine tastings of the estate’s signature labels. It's luxury, comfort and wine - all in one unforgettable package. Read more

Guest rating: 9.1 (superb)

Price from: $ 346 /night Set dates

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51
Castello Di Tornano Wine Relais

Tuscany (Gaiole in Chianti) View map

Forget the cliché postcard Tuscany - Castello di Tornano is where medieval grit meets modern indulgence. Yes, it’s an actual castle, with turrets, stone walls, and a past that stretches back to the 11th century, but these days the draw is less about knights and more about Chianti wine. Inside, rooms keep their fortress charm and outside lies the swimming pool that's carved into the hillside (castle owners of the past would be jealous)... Come for the wine, stay for the atmosphere, and leave with the smug satisfaction of saying, “Oh, I slept in a Tuscan castle.” Would we go back? In a heartbeat. Read more

Guest rating: 9.1 (superb)

Price from: $ 296 /night Set dates

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52
Fattoria di Rignana Winery BnB

Tuscany (Greve in Chianti) View map

In the rolling Chianti hills, Fattoria di Rignana Winery BnB feels like stepping into a slower, more soulful Tuscany. The views stretch endlessly over vineyards and olive groves, with an infinity pool perfectly positioned to make you pause and take it all in. Our room had an authentic, rustic charm-stone walls, wooden beams, and sunlight spilling in through a window that framed the countryside... Mornings began with homemade cakes, local cheeses, and freshly brewed coffee, the kind of breakfast that makes you want to linger a little longer. The estate’s wines are poured with pride, each glass carrying a sense of place, and dinners at the nearby restaurant were some of the best we had in Italy. The winding drive to reach it adds to the sense of arrival, and while not everything is polished, that’s exactly what makes it feel real. It’s a place for those who want the true Chianti experience - warm, generous, and unforgettable. Read more

Guest rating: 9.1 (superb)

Price from: $ 193 /night Set dates

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53
Fattoria Poggerino

Tuscany (Radda in Chianti) View map

As self-proclaimed wine hotel experts we’ve tasted many Tuscan stays, yet Fattoria Poggerino remains exceptional. Set deep in Chianti Classico on 43 hectares of organic vines & olive groves at 500 meters elevation. Speckled across converted stone farmhouses are 11 cosy rooms with views over Sangiovese rows. Your day begins with a lovely home-made breakfast served on the terrace, where the landscape itself feels like part of the meal... The winemaking at Poggerino is meticulous and organic, overseen by Piero Lanza, who tends the soils with fanatical care. Barrel-ageing in Slavonian or French oak brings out rich fruit and velvety tannins - Chianti Classico Riserva Bugialla has even earned Wine Spectator Top 100 mentions. Tastings begin among the vines, glide into cellar tours, and unfold into guided flights that reveal depth and structure. Guests often note how approachable the wines are - despite their complexity. Guests can also enjoy family-style dinners, cooking-classes, and leisurely moments by the infinity pool. Poggerino truly delivers a experience you'll want to return to. Read more

Guest rating: 9.1 (superb)

Price from: $ 138 /night Set dates

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54
Le Filigare Winery & Accomodation in Chianti

Tuscany (San Donato in Poggio) View map

Chianti has certainly no shortage of wine hotels, but Le Filigare Winery & Accommodation is one that truly captures the essence of the region. This 15th-century farm, perched between Florence and Siena, is surrounded by 60 hectares of vineyards and olive groves - the very landscape that gave Chianti its worldwide reputation. The 15 apartments and villas are designed with rustic-chic interiors, fully equipped kitchens, and panoramic terraces... Perfect for sipping a glass of their estate Chianti Classico as the sun drops behind the hills. Guests can join guided tastings in the cellar, stroll among the vines, or simply enjoy the silence that comes with being in the heart of wine country. Book now! Read more

Guest rating: 9.1 (superb)

Price from: $ 693 /night Set dates

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55
Villa Campomaggio Resort & SPA

Tuscany (Radda in Chianti) View map

We’d long been curious about Villa Campomaggio Resort & SPA, and it turned out to be every bit as charming as we’d hoped. Located between Radda and Greve in the heart of Chianti region, this 18th-century villa offers the kind of peaceful, vineyard-surrounded setting that feels instantly restorative. The rooms and suites are warm and traditional, with terracotta floors, wood-beamed ceilings, and windows that open onto olive trees and vine-covered hills... It’s the sort of place where time slows down - and where mornings start with a generous breakfast under the pergola - and afternoons drift by between the pool, the spa, and a glass of Sangiovese in the garden. We loved how easy everything felt-relaxed but well cared for, with friendly staff and just the right amount of attention. Quiet, scenic, and full of Tuscan character, exactly what a Chianti wine stay should be. Read more

Guest rating: 9.1 (superb)

Price from: $ 212 /night Set dates

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56
Borgo Tre Rose

Tuscany (Valiano) View map

The borderlands between Tuscany and Umbria aren’t just breathtaking-they’re also home to some of Italy’s most underrated winery hotels. Borgo Tre Rose is a perfect example, a hilltop estate where the vineyard views seem to stretch into two regions at once. Part of the historic Tenute del Cerro winery, it offers the full Tuscan experience - Chianti Colli Senesi and Vino Nobile di Montepulciano poured just steps from where the grapes are grown... You can join tastings, tour the cellars, or wander the vine-lined trails before ending the day with dinner on the terrace, watching the sun sink behind the hills. Rooms are rustic yet refined, the pool overlooks the vineyards, and the whole place feels like a slice of old Tuscany - only with a glass of something very, very good in hand. Read more

Guest rating: 9.0 (superb)

Price from: $ 183 /night Set dates

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57
Fattoria Casagrande

Tuscany (Rignano sullʼArno) View map

This former residence of an aristocratic Florentine family dates back centuries, and you can truly feel that heritage in its grand halls, frescoed ceilings, and sweeping stone staircases. The estate is still surrounded by its vineyards and olive groves, producing classic Chianti wines that you can taste on-site, often in the atmospheric cellars where barrels rest beneath vaulted arches. The accommodation is spread across charming apartments and suites, some with kitchenettes and rustic details that make longer stays easy and comfortable... Between vineyard walks, poolside afternoons, and wandering through medieval streets you'll start regretting not booking a longer stay. Read more

Guest rating: 9.0 (superb)

Price from: $ 116 /night Set dates

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58
Agriturismo Fattoria Lavacchio

Tuscany (Pontassieve) View map

During a road trip in the Florentine hills we found Agriturismo Fattoria Lavacchio. An absolutely stunning organic farm and winery. Here, Sangiovese grapes thrive under the Tuscan sun, producing Chianti Rufina wines that you can taste right where they’re made. You can book one of their 20 guest rooms and participate in vineyard tours, olive oil tastings, and even pasta-making workshops. The rooms and apartments balance rustic Tuscan style with comfort, making it easy to settle in for a few days of slow living... There’s also a swimming pool with sweeping vineyard views, hiking trails through olive groves, and a farm-to-table restaurant where everything tastes as fresh as the land around you. Fattoria Lavacchio is hands down one of our favourite hotels in the region. Read more

Guest rating: 8.9 (fabulous)

Price from: $ 144 /night Set dates

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59
Locanda Del Molino

Tuscany (Cortona) View map

Locanda del Molino is one of those rare finds in Tuscany where food, wine, and charm come together in a perfect combination. Once an old olive mill it has now been transformed to a cozy countryside inn, with just a handful of rooms - each full of rustic character and views over the rolling fields. What sets it apart is the restaurant: a celebration of Tuscan flavours, paired with wines from its sister estate, Il Falconiere. After long, lazy meals, you can retreat to the quiet of the inn or explore nearby Cortona... Intimate, authentic, and warmly run makes this place perfect for travellers who want a true taste of Tuscany without the crowds. Read more

Guest rating: 8.9 (fabulous)

Price from: $ 122 /night Set dates

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60
Buonamico Wine Resort

Tuscany (Montecarlo) View map

If you thought Tuscan winery stays were all about rustic stone walls and grandma’s recipes, think again. Instead, Buonamico Wine Resort has gone sleek, sexy, and unapologetically modern. Think infinity pool with vineyard views, a spa that practically begs you to stay another day, and rooms that look like they belong in a glossy design mag. But don’t worry, the soul of Tuscany is still front and center - in your glass... Buonamico’s cellar turns out everything from spritzy Vermentino to bold Sangiovese that’ll have you rethinking your life choices (like why you don’t live here). Pair it with the restaurant’s playful twist on Tuscan classics, and you’ve got yourself a stay that’s less farmstay nostalgia, more vino-fueled holiday with style. Read more

Guest rating: 8.8 (fabulous)

Price from: $ 171 /night Set dates

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61
Castello di Bossi

Tuscany (Castelnuovo Berardenga) View map

Winding our way through the Tuscan landscape, we finally ended up at Castello di Bossi. We’d stayed at several hotels on our summer trip, but this one would quickly become a highlight. The warm, welcoming staff and the centuries-old castle setting felt like stepping into another world. Our suite overlooked row upon row of Sangiovese, Cabernet, and Merlot vines stretching toward the horizon. Days slipped by between lazy hours at the pool and tastings of Chianti Classico and the estate’s bold Super Tuscans... Evenings brought long dinners where peppery olive oil, earthy pecorino, and rich ragù met the wines grown just beyond the terrace. Their Riserva and Gran Selezione wines were standouts - we only wished we could have brought home a case or two more. Read more

Guest rating: 8.8 (fabulous)

Price from: $ 199 /night Set dates

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62
Cignella Resort

Tuscany (Trequanda) View map

Set in stunning sceneries in Trequanda, Cignella Resort is a transformed 200-year-old farm that now feels like a modern Tuscan village. Complete with traditional stone, reclaimed beams, and thoughtful design touches that honor its history. The hotel's 14 unique villas and apartments - each overlooking the garden - offers its own terrace for slow mornings and evening wine moments. Other highlights include the possibility to explore hilltop towns, cycle through gentle hills, or unwind by the seasonal pool with a glass of wine... Cignella hits that sweet spot between Tuscan authenticity and modern ease. Read more

Guest rating: 8.7 (fabulous)

Price from: $ 224 /night Set dates

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63
Poderi Arcangelo

Tuscany (San Gimignano) View map

Tuscany has no shortage of postcard-worthy stays, but Poderi Arcangelo near San Gimignano hits the sweet spot: it’s a working winery, a rustic-chic agriturismo, and a front-row seat to some of the best views in Chianti country. The estate is split across three lovingly restored farmhouses, each with terracotta floors, wooden beams, and that cozy Tuscan farmhouse vibe... Rooms and apartments are simple yet stylish, and the kind of place where you’ll happily throw open the shutters in the morning just to stare at vineyards rolling into the horizon. Of course, the main attraction is what’s in your glass. Poderi Arcangelo produces a lineup that spans Vernaccia di San Gimignano, Chianti, and bold Super Tuscans, and tastings are all about celebrating what the land gives. When you’re not sipping or eating, you can float in the pool with the towers of San Gimignano in the distance, or wander into town for a gelato and a stroll through history. Book a few nights here and let the vineyards shape your days - we think you're going to love it. Read more

Guest rating: 8.7 (fabulous)

Price from: $ 187 /night Set dates

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64
Si Montalcino Hotel

Tuscany (Montalcino) View map

On the edge of one of Italy’s most celebrated wine towns, Si Montalcino Hotel offers a contemporary twist on the classic Tuscan escape. Just minutes from the vineyards that give life to Brunello di Montalcino, the hotel makes an ideal base for exploring one of the world’s great wine regions. The rooms are modern, bright, and comfortable, many with balconies overlooking the valley and its endless rows of vines... A swimming pool with panoramic views invites slow afternoons, while the restaurant highlights regional flavours paired with bottles from nearby estates - including, of course, Brunello. Read more

Guest rating: 8.7 (fabulous)

Price from: $ 159 /night Set dates

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65
Tenuta delle Rose

Tuscany (Montaione) View map

Imagine arriving at Tenuta delle Rose - a restored Tuscan countryside estate that unfolds like a mini‑village. Complete with its own piazza and bubbling fountain at the heart of it all. Each of the ten apartments is lovingly named after a Decameron narrator, nestled among vineyards, olive groves, and herb‑scented gardens-feels like a storybook brought to life. We stayed in a bright, rustic‑chic apartment that opens onto sunlit terraces and cozy corners shaded by olive trees... Outside, the gardens are a dreamy mosaic of olive groves, herb meadows, and poplar paths. You can sunbathe poolside, wander the vine-framed trail to the bocce court, or pick fresh produce straight from the garden. This certainly is the ideal place for exploring Florence, Siena, or Pisa by day and returning to a calm hideaway in the evening. Read more

Guest rating: 8.7 (fabulous)

Price from: $ 271 /night Set dates

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66
Torciano Hotel Wine & Winery

Tuscany (San Gimignano) View map

Tuscany is a land where vineyards meet sunrise, where every sip of wine feels eternal - but some places make that feeling even more vivid. Torciano Hotel Wine & Winery, just outside San Gimignano, does exactly that. At Torciano, you don’t just stay - you become part of the vineyard story. Housed in a lovingly restored rural building, this boutique hotel offers romantic, terracotta-floored rooms and sweeping views of vineyards that ripple across the hills. The wine experience here is of course amazing... It’s just minutes to Tenuta Torciano’s cellar - where tastings, oil samplings, and lunches amid the vines are available year-round. Other activities include exploring vineyard tours, joining cooking or truffle-hunting classes, or simply letting time slow with a glass in hand on the terrace. We love it! Read more

Guest rating: 8.7 (fabulous)

Price from: $ 217 /night Set dates

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67
Agriturismo Bio Fattoria Bacio

Tuscany (Certaldo) View map

As self-proclaimed wine hotel experts we have seen many fantastic places around Italy. But Agriturismo Bio Fattoria Bacio in the hills near Certaldo felt truly special. Surrounded by 90 hectares of organic vineyards and olive trees, this 17th-century villa is both peaceful and full of soul. The rooms and apartments are rustic, charming, and equipped with everything you need - some with views stretching across the Chianti countryside... Days here start with generous homemade breakfasts and often end with estate wine, shared stories, and hearty Tuscan dinners prepared by the family. You can also participate in cooking classes and tastings of their own wines right where they’re made. It’s honest, warm, and exactly what you hope for in a countryside wine stay. Read more

Guest rating: 8.4 (very good)

Price from: $ 191 /night Set dates

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68
Agriturismo Streda Wine & Country Holiday

Tuscany (Vinci) View map

This gorgeous, family-run, retreat spans around 80 hectares of vineyards and olive groves in Vinci, Tuscany. It is built in 3 historic farmhouses, each converted into spacious apartments and rooms. Mornings begin with generous breakfasts-local cheese, honey, jams-before heading down to the estate’s on-site winery. The guided tastings reveal the depth of their Chianti-style reds and olive-oil, often paired with farm-to-table lunches at Leonardo’s Place... Afternoons invite to lazy swims in the saltwater or rooftop pool, bike rides through vine-draped hills, and activities like horseback riding or cooking classes. We love it! Read more

Guest rating: 8.4 (very good)

Price from: $ 134 /night Set dates

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69
Rocca Di Castagnoli

Tuscany (Gaiole in Chianti) View map

Deep in Chianti Classico, Rocca di Castagnoli combines centuries of history with a working winery at its core. Once a medieval fortress, today it’s both a boutique agriturismo and the heart of an estate producing some of the region’s most respected wines. Stay here and you’re surrounded by vineyards and olive groves, with views that stretch across rolling Tuscan hills... The rooms and apartments carry rustic elegance – terracotta floors, wooden beams, and stone walls that speak to the estate’s past, paired with modern comforts for a relaxed stay. The real highlight however is the connection to the winery. Guests can tour the historic cellars, join tastings, and learn firsthand what makes this corner of Tuscany so distinctive. Between vineyard walks, poolside afternoons, and leisurely meals paired with the estate’s bottles, life quickly falls into the Tuscan rhythm. Read more

Guest rating: 8.4 (very good)

Price from: $ 179 /night Set dates

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70
Borgo Casa al Vento

Tuscany (Gaiole in Chianti) View map

The Chianti Classico wine region isn’t just marked on maps - it’s marked in the vineyards themselves with the famous black rooster emblem. A centuries-old symbol of quality you’ll definitely spot at the fantastic Borgo Casa al Vento. Set near Gaiole in Chianti, this restored medieval hamlet is now a working organic winery where guests can taste Chianti Classico right where the grapes are grown, wander the vine rows, or join in the grape harvest when the season arrives... Stone houses and intimate rooms overlook rolling hills, the restaurant serves estate-grown produce alongside their wines, and the pool offers panoramic views you’ll want to toast again and again. It’s Chianti living at its most authentic. Read more

Guest rating: 8.3 (very good)

Price from: $ 225 /night Set dates

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71
Fattoria Di Corsignano

Tuscany (Vagliagli) View map

In the hills just outside Siena, Fattoria di Corsignano successfully combines boutique hospitality with a working organic winery. The hotel’s rustic villas and suites overlook rows of Sangiovese vines, inviting you to wake up to the essence of Chianti Classico. Here, wine is everywhere: from guided tastings and cellar tours to dinners where each course is paired with estate labels. Add in a pool, olive groves, and the timeless Tuscan landscape, and the pace of life quickly slows to match the rhythm of the vineyard... If you’re dreaming of an authentic stay where wine and Tuscany go hand in hand, Corsignano is hard to beat! Read more

Guest rating: 8.3 (very good)

Price from: $ 267 /night Set dates

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72
Hotel Villa Casalecchi

Tuscany (Castellina in Chianti) View map

The combination of historic charm and Chianti flair makes Hotel Villa Casalecchi a standout wine retreat above Castellina. Situated on 50 hectares of woodlands, olive groves, and vineyards, the property delivers panoramic countryside views from its terrace and pool. Suites and rooms - found in the villa or poolside annex - feature antique furnishings, rustic décor, and modern comforts like air-conditioning and Wi‑Fi... Breakfast buffets combine Italian pastries and savory options, while evening happy hours and a bar invite you to enjoy Chianti Classico pours under cypress-lined skies. Villa Casalecchi truly feels like a Tuscan home - perfect for wine lovers seeking an authentic stay. Read more

Guest rating: 8.3 (very good)

Price from: $ 241 /night Set dates

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20 of 72 hotels

Hotels with winery in Tuscany Nowhere else on Earth packs in more winery accommodations than Tuscany, Italy. On this page, you’ll find a curated list with only the best hotels that has either a winery or a vineyard. Places that actually put you close to the vines and let you enjoy those iconic Italian views at breakfast, cellar tastings by afternoon, and a glass of Chianti by the pool at sunset.

The different hotels we have picked range from rustic agriturismi to luxurious, sleek, estates near classic hill towns. We’ve put a lot of effort into reviewing every place, so you can focus on the fun part: choosing the vibe, pack your bags and then letting Tuscany do the rest. Cheers!

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