Find hotels in Chianti Region from ¥10,853

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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
The price is ¥19,771
¥22,485 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Borgo di Pietrafitta Relais

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 ¥17,574
¥20,065 total
includes taxes & fees
Jan 5 - Jan 6, 2026
La Certosa di Pontignano

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

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 ¥18,492
¥20,341 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Villa Cassia di Baccano

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 ¥17,321
¥19,787 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Casa di Palaia

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 ¥14,378
¥16,091 total
includes taxes & fees
Jan 18 - Jan 19, 2026
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

COMO Castello Del Nero

COMO Castello Del Nero
5.0 star property
Barberino Tavarnelle
9.6 out of 10, Exceptional, (133)
Surrounded by rolling hills, this elegant hotel offers two restaurants serving international cuisine. Enjoy complimentary breakfast before exploring nearby Castello di Barberino Val d'Elsa or unwinding with hot stone massages and Ayurvedic treatments at the spa.

"Wonderful stay. 5-stars across the board if you’re looking for disconnecting and relaxing in the rolling hills of the Tuscan countryside. Easy day/dinner trips to Florence or Siena (rental car). "
United States
Matthew
The price is ¥138,035
¥153,308 total
includes taxes & fees
Jan 5 - Jan 6, 2026
COMO Castello Del Nero

Agriturismo Nerbona

Agriturismo Nerbona
Colle di Val d'Elsa
9.6 out of 10, Exceptional, (18)
Discover rural Tuscan charm at this countryside retreat with a refreshing seasonal pool, free bike rentals, and volleyball court. Perfectly positioned near Archeological Museum and Il Palagio Winery, with convenient parking for day trips.

"Very nice place"
United States
JULISSA
The price is ¥27,100
¥30,177 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Agriturismo Nerbona

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

Villa San Lucchese

Villa San Lucchese
4.0 star property
Poggibonsi
9.4 out of 10, Exceptional, (336)
Escape to this historic family-friendly hotel offering free breakfast and parking. Enjoy the seasonal outdoor pool and tennis courts, then unwind at the bar. Conveniently located near San Lucchese Convent and local Tuscan villages with train station access.

"Beautiful place Great service "
United States
patricia
Villa San Lucchese

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 ¥12,861
¥15,250 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Hotel Borgo di Cortefreda Relais

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

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 ¥17,873
¥20,394 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Relais Poggio Borgoni

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 ¥14,863
¥20,035 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Hotel Il Viandante

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 ¥14,187
¥20,012 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Antica Pieve B&B

Villa Castiglione

Villa Castiglione
2.0 star property
Impruneta
8.6 out of 10, Excellent, (256)
Escape to this family-friendly hotel featuring an outdoor pool, children's splash area, and poolside bar. Just 15 minutes from Florence attractions like Pitti Palace and Ponte Vecchio, with free breakfast, WiFi, and parking.

"Nice and cute place. Great price. "
United States
Jozsef
The price is ¥9,364
¥10,853 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Villa Castiglione

Hotel Colle Etrusco Salivolpi

Hotel Colle Etrusco Salivolpi
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (115)
"Friendly staff and walking distance to town"
United States
Scott
Hotel Colle Etrusco Salivolpi

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 ¥16,109
¥18,089 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Villa Casagrande Resort & SPA

Castello Di Montemasso

Castello Di Montemasso
Greve in Chianti
10.0 out of 10, Exceptional, (12)
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.

"Sanja and her husband were amazing hosts. They made sure we had everything we needed. The place was so beautiful and comfortable. We loved it!!!"
United States
Kathleen
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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