Chianti Region Hotels with Swimming Pool

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Check availability on Chianti Region Hotels with Swimming Pools

Our top choices for Chianti Region hotels with a pool

Outdoor pool, pool loungers
Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
9.4 out of 10, Exceptional, (169)
"Wonderful setting."
United Kingdom
Simon
The price is RM468
RM534 total
includes taxes & fees
3 Jan - 4 Jan 2026
Borgo di Pietrafitta Relais
Seasonal outdoor pool, open 9:00 AM to 7:00 PM, pool loungers
Villa Cassia di Baccano

Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (23)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is RM592
RM652 total
includes taxes & fees
7 Jan - 8 Jan 2026
Villa Cassia di Baccano
Seasonal outdoor pool, open 9:00 AM to 7:00 PM, pool umbrellas
Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais
4.0 star property
Barberino Tavarnelle
9.4 out of 10, Exceptional, (478)
"The views were spectacular and the grounds were so peaceful"
United States
Michelle
The price is RM390
RM457 total
includes taxes & fees
6 Jan - 7 Jan 2026
Hotel Borgo di Cortefreda Relais
Seasonal outdoor pool, pool loungers
Castello di Meleto

Castello di Meleto

Castello di Meleto
Gaiole in Chianti
8.8 out of 10, Excellent, (90)
"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
Exterior
Casa di Palaia

Casa di Palaia

Casa di Palaia
Greve in Chianti
10.0 out of 10, Exceptional, (22)
"Very well located in the heart if the Tuscany region."
United States
Eli
The price is RM354
RM409 total
includes taxes & fees
14 Dec - 15 Dec
Casa di Palaia
Outdoor pool, pool loungers
Molino di Foci

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
Seasonal outdoor pool, pool loungers
Villa il Fedino

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (97)
"Great people, great location great service"
Canada
James
The price is RM600
RM679 total
includes taxes & fees
7 Jan - 8 Jan 2026
Villa il Fedino
Indoor pool, seasonal outdoor pool, pool loungers
Hotel Palazzo San niccolò & Spa

Hotel Palazzo San niccolò & Spa

Hotel Palazzo San niccolò & Spa
4.0 star property
Radda in Chianti
9.2 out of 10, Wonderful, (176)
"Ideal country setting"
Canada
Dee
The price is RM436
RM508 total
includes taxes & fees
21 Dec - 22 Dec
Hotel Palazzo San niccolò & Spa
Front of property – evening/night
Resort 37

Resort 37

Resort 37
4.0 star property
Rignano sull'Arno
9.8 out of 10, Exceptional, (36)
"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 RM897
RM999 total
includes taxes & fees
7 Jan - 8 Jan 2026
Resort 37
2 outdoor pools, a rooftop pool, pool loungers
Agriturismo La Forra

Agriturismo La Forra

Agriturismo La Forra
Cavriglia
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
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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Hotels with pools and free breakfast in Chianti Region

Exterior
Il Borro - Relais & Châteaux

Il Borro - Relais & Châteaux

Il Borro - Relais & Châteaux
Loro Ciuffenna
9.2 out of 10, Wonderful, (99)
The price is RM1,771
RM1,948 total
includes taxes & fees
21 Dec - 22 Dec
Il Borro - Relais & Châteaux
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4-star hotels with pools in Chianti Region

Seasonal outdoor pool, open 9:00 AM to 7:00 PM, pool umbrellas
Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais
4.0 star property
Barberino Tavarnelle
9.4 out of 10, Exceptional, (478)
The price is RM390
RM457 total
includes taxes & fees
6 Jan - 7 Jan 2026
Hotel Borgo di Cortefreda Relais
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

Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort

10/10 Excellent
"Very clean,staff was very kind and helpful. Looking forward to come back! 😊"
Andrea 2-night trip
Posted 5 days ago
Castello di Fonterutoli Wine Resort

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