Chianti Region Hotels from from S$69

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Chianti Region hotels

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
Borgo di Pietrafitta Relais

Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais
4.0 star property
Barberino Tavarnelle
9.4 out of 10, Exceptional, (480)
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 S$120
includes taxes & fees
6 Jan - 7 Jan
Hotel Borgo di Cortefreda Relais

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 cosy 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 S$167
includes taxes & fees
26 Jan - 27 Jan
Hotel Il Viandante

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 S$164
includes taxes & fees
7 Jan - 8 Jan
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

Relais Poggio Borgoni

Relais Poggio Borgoni
San Casciano in Val di Pesa
9.8 out of 10, Exceptional, (58)
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 S$152
includes taxes & fees
11 Jan - 12 Jan
Relais Poggio Borgoni

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 savour 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 S$128
includes taxes & fees
7 Jan - 8 Jan
Casa di Palaia

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.

"It’s beautiful place! "
United States
Tatihana
The price is S$145
includes taxes & fees
21 Jan - 22 Jan
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 S$126
includes taxes & fees
1 Feb - 2 Feb
Torrebianca Tuscany

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

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 S$224
includes taxes & fees
13 Jan - 14 Jan
Villa il Fedino

Antica Pieve B&B

Antica Pieve B&B
Barberino Tavarnelle
9.4 out of 10, Exceptional, (14)
Set in Barberino Tavarnelle near Abbey of Passignano, this inviting B&B offers a refreshing pool with poolside bar, garden terrace, and massage services. Free breakfast, WiFi and parking enhance the authentic countryside experience.

"Very nice stay here! Great breakfast and coffee every morning. Great location to tour around to different wineries and towns. Free parking. "
Canada
Jessica
The price is S$164
includes taxes & fees
24 Jan - 25 Jan
Antica Pieve B&B

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

Hotel Colle Etrusco Salivolpi

Hotel Colle Etrusco Salivolpi
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (116)
"Friendly staff and walking distance to town"
United States
Scott
Hotel Colle Etrusco Salivolpi

Fattoria Lornano Winery

Fattoria Lornano Winery
Monteriggioni
8.0 out of 10, Very good, (5)
Experience rural Italian charm at this wine-producing farm stay near Monteriggioni Castle. The property offers an outdoor pool, free WiFi, and parking. Enjoy nearby hiking trails and easy access to local wineries, all just a short walk from Badesse Station.

"The staff were so friendly and polite to us during our stay. Such a gem of a place to stay and we are very happy we chose to stay there "
Canada
Tamara
Fattoria Lornano Winery

Hotel Villa Cesi

Hotel Villa Cesi
4.0 star property
Impruneta
8.6 out of 10, Excellent, (70)
Unwind at this Tuscan retreat featuring regional cuisine at Ristorante Sassi Neri and a welcoming bar. The 24-hour fitness centre keeps routines intact while easy access to Florence's Piazzale Michelangelo and Pitti Palace ensures perfect sightseeing opportunities.

"We had a wonderful stay."
United Kingdom
Kanhaiya
Hotel Villa Cesi

Agriturismo La Forra

Agriturismo La Forra
Cavriglia
9.6 out of 10, Exceptional, (14)
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 centre 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

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 S$287
includes taxes & fees
11 Jan - 12 Jan
Resort 37

Dimora Casa Eugenia

Dimora Casa Eugenia
Loro Ciuffenna
9.2 out of 10, Wonderful, (32)
Scenic mountain biking trails surround this family-friendly guesthouse where complimentary breakfast is served daily. The rooftop terrace provides stunning views after exploring nearby San Pietro a Gropina and Mulino Ad Acqua attractions.

"Beautiful boutique type stay. They are so welcoming and kind. Room was spacious, bed was comfortable. Breakfast was very tasty. Walked around the village and it was beautiful. Not one complaint, book your stay! "
United States
Shannon
Dimora Casa Eugenia

Torraccia di Chiusi

Torraccia di Chiusi
San Gimignano
10.0 out of 10, Exceptional, (97)
"A beautiful base for exploring Tuscany away from the crowds."
United States
Anthony
The price is S$321
includes taxes & fees
22 Jan - 23 Jan
Torraccia di Chiusi
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.

Holiday Rentals in Chianti Region

Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Mediterranean Region attractions

Learn more about Chianti Region

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

Chianti Region featuring farmland

Top Chianti Region Hotel Reviews

More cheap stays in Chianti Region

Hotels in Chianti Region with star rating

Explore a world of travel with Expedia