Find hotels in Chianti Region from ₩82,525

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Our top choices for Chianti Region hotels

La Certosa di Pontignano

La Certosa di Pontignano
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (503)
Soak in Tuscany from the rooftop terrace at this charming Castelnuovo Berardenga retreat. The on-site restaurant serves Italian cuisine throughout the day, while the garden setting creates a peaceful atmosphere. Terra di Seta and free perks like WiFi, parking, and breakfast add value.

"Excellent place to stay even for the next time. "
Canada
Xuejie
The price is ₩121,729
₩140,829 total
includes taxes & fees
Dec 23 - Dec 24
La Certosa di Pontignano

Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
9.4 out of 10, Exceptional, (169)
Set amidst Castellina in Chianti, this family-friendly farm stay features an attached winery and refreshing outdoor pool. Enjoy complimentary WiFi and parking while exploring nearby Casa Vinicola Luigi Cecchi and Castellina Fortress, or unwind with massages and garden views.

"Wonderful setting."
United Kingdom
Simon
The price is ₩168,290
₩192,039 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Borgo di Pietrafitta Relais

Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (23)
Escape to this charming Italian affittacamere featuring a seasonal outdoor pool, poolside bar, and full-service spa. Located near La Salceta Winery and Il Borro Wines, guests enjoy free breakfast, WiFi, and parking. Children's pool adds family appeal.

"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is ₩213,068
₩234,375 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Villa Cassia di Baccano

Castello di Meleto

Castello di Meleto
Gaiole in Chianti
8.8 out of 10, Excellent, (91)
Immerse yourself in authentic Tuscany at this historic castle estate. Enjoy wine tastings at the on-site winery, cool off in the seasonal outdoor pool, and dine at La Fornace di Meleto restaurant. Free WiFi and parking complement the beautiful garden and terrace settings.

"This Castle is AMAZING! Agatha and Victor so kind. I highly recommend this place. Wines are extremely wonderful. We really enjoy the staying."
United States
Karem
Castello di Meleto

Hotel Il Viandante

Hotel Il Viandante
3.0 star property
Terranuova Bracciolini
9.2 out of 10, Wonderful, (162)
Located in Terranuova Bracciolini, this welcoming hotel offers a cozy bar/lounge and convenient coffee shop. Just minutes from Il Cassero and a short drive from Montevarchi Station, guests consistently praise the attentive staff that enhance your Italian getaway.

"Arrived very late due to flight delay , communication and support from the hotel about late check in was fantastic and the owner even stayed until I arrived at 00.30. Recommended."
United Kingdom
James
The price is ₩139,508
₩188,060 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Hotel Il Viandante

Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA
4.0 star property
Figline e Incisa Valdarno
9.2 out of 10, Wonderful, (375)
Escape to this Tuscan retreat featuring 2 restaurants, a winery, and full spa services. Enjoy deep-tissue massages after exploring nearby Franciscan Monastery. Just a 12-minute walk from Figline Valdarno Station with free WiFi and parking for convenient travel.

"We had a great stay and loved the 2 bedrooms as a family of 4. Very friendly and accommodating staff"
Canada
Stefanie
The price is ₩140,379
₩157,870 total
includes taxes & fees
Jan 20 - Jan 21, 2026
Villa Casagrande Resort & SPA

Torrebianca Tuscany

Torrebianca Tuscany
Rignano sull'Arno
9.6 out of 10, Exceptional, (40)
Immerse yourself in Rignano sull'Arno at this welcoming B&B offering complimentary cooked-to-order breakfast, WiFi, and parking. Located near Fashion Groove and The Mall Luxury Outlet, with Reggello Station just 4 minutes away by car.

"Lovely pool Breakfast good"
United Kingdom
christine
The price is ₩152,269
₩170,091 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Torrebianca Tuscany

Molino di Foci

Molino di Foci
1.0 star property
San Gimignano
9.4 out of 10, Exceptional, (47)
"Breakfast was fresh and beautifully presented in the atrium with a view of the Tuscan landscape. "
Canada
Diego
Molino di Foci

Castello di Volpaia

Castello di Volpaia
3.0 star property
Radda in Chianti
9.6 out of 10, Exceptional, (65)
This historic Radda farm stay enchants with its winery, Italian cuisine at Osteria Volpaia, and both indoor and outdoor pools. Explore renowned wine tastings near Volpaia and Castello di Albola while enjoying free WiFi and convenient parking.

"A beautiful property with amazing views. The staff is very nice, the room was wonderful and food options were excellent. I highly recommend staying here. The tour of the winery was also fantastic. I loved my time here. "
United States
Gabrielle
The price is ₩293,296
₩329,545 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Castello di Volpaia

Casa di Palaia

Casa di Palaia
Greve in Chianti
10.0 out of 10, Exceptional, (22)
Surrounded by Chianti's rolling hills, this guesthouse offers free breakfast, WiFi, and private pools. Visit nearby Sezzate and Verrazzano Castles, then return to savor a meal at the on-site restaurant after a day of exploring.

"Very well located in the heart if the Tuscany region."
United States
Eli
The price is ₩127,397
₩147,057 total
includes taxes & fees
Dec 22 - Dec 23
Casa di Palaia

Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais
4.0 star property
Barberino Tavarnelle
9.4 out of 10, Exceptional, (478)
Experience Tuscan charm at this hillside hotel with outdoor pool and poolside bar. Enjoy local cuisine at Ristorante Cortefreda after a day of massages at the spa. Near Abbey of Passignano and Casa Sola Winery with helpful staff to enhance your stay.

"The views were spectacular and the grounds were so peaceful"
United States
Michelle
The price is ₩124,445
₩147,264 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Hotel Borgo di Cortefreda Relais

Agriturismo La Posta Reale

Agriturismo La Posta Reale
Castiglion Fibocchi
9.0 out of 10, Wonderful, (2)
Escape to this charming Castiglion Fibocchi farm stay featuring an attached winery and regional cuisine at Osteria Le 4 Lire restaurant. Explore nearby Il Borro Wines and Fattoria La Vialla with convenient free parking and WiFi throughout your countryside retreat.

"Our host was very attentive and lovely. She invited us to a very nice evening wine party on-site aside of a small lake. It was quite charming. It was also nice to see the vineyards and olive trees. One downside was no A/C as advertised, but we had fans. Still very quaint."
United States
Michael
Agriturismo La Posta Reale

Resort 37

Resort 37
4.0 star property
Rignano sull'Arno
9.8 out of 10, Exceptional, (37)
Escape to this Tuscan hotel where you can swim in the seasonal outdoor pool and play tennis. Enjoy meals at Ristorante Al Pruno or visit the bar/lounge. Free breakfast, WiFi, and parking enhance your stay near Castello di Volognano.

"Excellent option if you are planning on shopping!! Food was outstanding, service was excellent and views were incredible. I wish we had stayed longer! "
United States
Kathy
The price is ₩322,739
₩359,338 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Resort 37

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (97)
Enchanting affittacamere featuring a seasonal outdoor pool, relaxing massage services, and convenient bar. Located near Monastary of Sorelle Clarisse and Antinori nel Chianti Classico, with complimentary breakfast, WiFi, and parking for a perfect Italian countryside retreat.

"Great people, great location great service"
Canada
James
The price is ₩215,867
₩244,374 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Villa il Fedino

Relais Poggio Borgoni

Relais Poggio Borgoni
San Casciano in Val di Pesa
9.8 out of 10, Exceptional, (57)
Sip local wines at this charming countryside retreat between Florence and Chianti. The seasonal outdoor pool, hot tub, and Osteria del Poggio restaurant create a relaxing Italian escape. Free breakfast, WiFi and parking complement the attentive service.

"Very personal, kind & sympathatic Staff. The Place is gorgeous."
Switzerland
Nils
The price is ₩152,374
₩174,532 total
includes taxes & fees
Dec 22 - Dec 23
Relais Poggio Borgoni

L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (12)
Set in Gaiole in Chianti with views of the Tuscan countryside, this affittacamere offers daily buffet breakfast and tranquil garden spaces. Explore nearby Medieval Tower of Barbischio or unwind on the scenic terrace after a day of wine tasting.

"Monica was the friendliest most enthusiastic host we’ve stayed with. Everything from her greeting to the amazing breakfast was perfect. She does a lot of baking, so the breakfast was really a treat and you could also get eggs cooked in various ways. The room was a little small but very comfortable. Parking was on the street, but it was fairly close and easy."
United States
Perry
L' Eroico

Hotel Palazzo San niccolò & Spa

Hotel Palazzo San niccolò & Spa
4.0 star property
Radda in Chianti
9.2 out of 10, Wonderful, (177)
Surrounded by Chianti vineyards, this spa hotel offers indulgent treatments, 2 restaurants, and both indoor and outdoor pools. Explore nearby Castello di Radda Winery or unwind at the poolside bar after a day in picturesque Tuscan countryside.

"Ideal country setting"
Canada
Dee
The price is ₩169,438
₩196,762 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Hotel Palazzo San niccolò & Spa

Agriturismo La Forra

Agriturismo La Forra
Cavriglia
9.4 out of 10, Exceptional, (13)
Immerse yourself in Tuscany at this family-friendly farm stay featuring 2 outdoor pools and local cuisine at La Cucina de La Forra. Explore nearby attractions while enjoying free breakfast and parking, plus fitness center and terrace amenities.

"Loved it! Super helpful at check-in telling us about everything that was available. We wrote horses for two hours at a very affordable price. The restaurant on site was was good and breakfast was wonderful. Hiking trails and views were amazing. Would definitely stay again. Nearest grocery and shopping were only about 15 minutes away in montevechi."
United States
Joshua or Stephani
Agriturismo La Forra

Locanda Il Gallo

Locanda Il Gallo
3.0 star property
Greve in Chianti
9.4 out of 10, Exceptional, (53)
Enjoy Italian countryside comfort at this Greve in Chianti hotel with complimentary breakfast and WiFi. After exploring nearby Sezzate and Verrazzano castles, unwind in the garden or savor drinks at the bar before ordering room service from the restaurant.

"The property owner was very helpful explaining wineries location and local food! The in-house restaurant was excellent and convenient! "
United States
Santina
The price is ₩235,914
₩264,702 total
includes taxes & fees
Dec 30 - Dec 31
Locanda Il Gallo

Castello Di Montemasso

Castello Di Montemasso
Greve in Chianti
10.0 out of 10, Exceptional, (11)
Wake up to complimentary full breakfast at this enchanting castle near Ruffino vineyards and Sezzate Castle. With free WiFi and daily housekeeping, this idyllic retreat offers the perfect base for exploring the rolling hills of Chianti.

"From the moment we arrived, we were welcomed with exceptional hospitality. The staff is outstanding, and we must give special recognition to Ivan and Sanja, whose professionalism, kindness, and genuine care made our stay unforgettable. They go above and beyond in every detail — every smile, every gesture reflects their passion and dedication. The place itself is magical, a true journey back in time. Every corner is rich with history, charm, and authenticity. The cleanliness is impeccable, and...
United States
Fabio
The price is ₩223,658
₩247,753 total
includes taxes & fees
Dec 24 - Dec 25
Castello Di Montemasso
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Take a sightseeing trip of Tuscany's renowned wine region and visit its vineyards, wineries, ancient churches, castles and hilltop villages.

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