Search Chalets in Chianti Region

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Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11
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Jan 23 - Jan 25
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Feb 20 - Feb 22
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Recommended hotels in Chianti Region

Exterior detail
La Certosa di Pontignano

Bed & Breakfast in Castelnuovo Berardenga

La Certosa di Pontignano
9.6 out of 10, Exceptional, (503)
"Excellent place to stay even for the next time. "
Canada
Xuejie
The price is ￥15,820
￥18,139 total
includes taxes & fees
Dec 26 - Dec 27
La Certosa di Pontignano
Deluxe Suite | Garden view
Villa Cassia di Baccano

Townhouse in Loro Ciuffenna

Villa Cassia di Baccano
9.4 out of 10, Exceptional, (23)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is ￥18,122
￥19,934 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Villa Cassia di Baccano
Seasonal outdoor pool, sun loungers
Castello di Meleto

Farmstay in Gaiole in Chianti

Castello di Meleto
8.8 out of 10, Excellent, (91)
"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
Outdoor pool, sun loungers
Borgo di Pietrafitta Relais

Farmstay in Castellina in Chianti

Borgo di Pietrafitta Relais
9.4 out of 10, Exceptional, (169)
"Wonderful setting."
United Kingdom
Simon
The price is ￥14,217
￥16,374 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Borgo di Pietrafitta Relais
Property entrance
Hotel Il Viandante

Hotel Il Viandante

Hotel Il Viandante
3.0 star property
9.2 out of 10, Wonderful, (162)
"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 ￥14,810
￥19,965 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Hotel Il Viandante
Outdoor dining
Torrebianca Tuscany

Bed & Breakfast in Rignano sull'Arno

Torrebianca Tuscany
9.6 out of 10, Exceptional, (40)
"Lovely pool Breakfast good"
United Kingdom
christine
The price is ￥14,645
￥16,386 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Torrebianca Tuscany
Exterior
Casa di Palaia

Guesthouse in Greve in Chianti

Casa di Palaia
10.0 out of 10, Exceptional, (22)
"Very well located in the heart if the Tuscany region."
United States
Eli
The price is ￥17,327
￥19,795 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Casa di Palaia
Dinner served, Regional cuisine
Agriturismo La Posta Reale

Farmstay in Castiglion Fibocchi

Agriturismo La Posta Reale
9.0 out of 10, Wonderful, (2)
"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
Property entrance
Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA
4.0 star property
9.2 out of 10, Wonderful, (375)
"It’s beautiful place! "
United States
Tatihana
The price is ￥16,416
￥18,425 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Villa Casagrande Resort & SPA
Front of property - evening/night
Resort 37

Resort 37

Resort 37
4.0 star property
9.8 out of 10, Exceptional, (37)
"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 ￥34,264
￥38,149 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Resort 37
Room amenity
Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais
4.0 star property
9.4 out of 10, Exceptional, (479)
"The views were spectacular and the grounds were so peaceful"
United States
Michelle
The price is ￥14,521
￥17,075 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Hotel Borgo di Cortefreda Relais
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas
Relais Poggio Borgoni

Farmstay in San Casciano in Val di Pesa

Relais Poggio Borgoni
9.8 out of 10, Exceptional, (57)
"Very personal, kind & sympathatic Staff. The Place is gorgeous."
Switzerland
Nils
The price is ￥18,732
￥21,340 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Relais Poggio Borgoni
Property entrance
Villa il Fedino

Townhouse in San Casciano in Val di Pesa

Villa il Fedino
9.6 out of 10, Exceptional, (97)
"Great people, great location great service"
Canada
James
The price is ￥22,002
￥24,937 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Villa il Fedino
Garden
Villa Castiglione

Villa Castiglione

Villa Castiglione
2.0 star property
8.6 out of 10, Excellent, (256)
"Nice and cute place. Great price. "
United States
Jozsef
The price is ￥10,305
￥11,889 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Villa Castiglione
2 outdoor pools, a rooftop pool, sun loungers
Agriturismo La Forra

Farmstay in Cavriglia

Agriturismo La Forra
9.4 out of 10, Exceptional, (13)
"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
Front of property
Locanda Il Gallo

Locanda Il Gallo

Locanda Il Gallo
3.0 star property
9.4 out of 10, Exceptional, (53)
"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 ￥25,046
￥28,102 total
includes taxes & fees
Dec 30 - Dec 31
Locanda Il Gallo
Aerial view
Castello Di Montemasso

Castle in Greve in Chianti

Castello Di Montemasso
10.0 out of 10, Exceptional, (11)
"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
The price is ￥24,034
￥26,622 total
includes taxes & fees
Dec 28 - Dec 29
Castello Di Montemasso
Exterior
Castello di Fonterutoli Wine Resort

Bed & Breakfast in Castellina in Chianti

Castello di Fonterutoli Wine Resort
9.4 out of 10, Exceptional, (201)
"Amazing experience all around! Stayed for 2 nights!"
Canada
Matthew
The price is ￥30,740
￥34,551 total
includes taxes & fees
Dec 27 - Dec 28
Castello di Fonterutoli Wine Resort
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas
Agriturismo Nerbona

Farmstay in Colle di Val d'Elsa

Agriturismo Nerbona
9.6 out of 10, Exceptional, (18)
"Very nice place"
United States
JULISSA
The price is ￥15,208
￥17,096 total
includes taxes & fees
Dec 27 - Dec 28
Agriturismo Nerbona
Lunch, dinner served; local cuisine, pool views
Villa il Poggiale - Dimora Storica

Inn in San Casciano in Val di Pesa

Villa il Poggiale - Dimora Storica
9.6 out of 10, Exceptional, (145)
"Wonderful stay."
United States
Nancy
The price is ￥19,870
￥22,041 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Villa il Poggiale - Dimora Storica
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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Top Chianti Region Hotel Reviews

Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais

10/10 Excellent
"The hotel and services exceeded my expectations."
Vili 2-night trip
Posted 1 month ago
Hotel Borgo di Cortefreda Relais

Find out more about Chianti Region

Chianti Region Chalets information

Number of reviews
2,705
Accommodation
0 Chalets
Lowest Price
￥11,889
Highest Price
￥38,149

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