Find Hotels with a Pool in Chianti Region

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Check availability on Chianti Region Hotels with a Pool

Our top choices for Chianti Region hotels with a pool

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 AED 526
AED 578 total
includes taxes & fees
7 Jan - 8 January 2026
Villa Cassia di Baccano

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 AED 419
AED 479 total
includes taxes & fees
3 Jan - 4 January 2026
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, (478)
"The views were spectacular and the grounds were so peaceful"
United States
Michelle
The price is AED 349
AED 410 total
includes taxes & fees
6 Jan - 7 January 2026
Hotel Borgo di Cortefreda Relais

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

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 AED 317
AED 366 total
includes taxes & fees
15 Dec - 16 Dec
Casa di Palaia

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 AED 527
AED 597 total
includes taxes & fees
7 Jan - 8 January 2026
Villa il Fedino

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

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 AED 804
AED 896 total
includes taxes & fees
7 Jan - 8 January 2026
Resort 37

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)
"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 AED 724
AED 813 total
includes taxes & fees
9 Jan - 10 January 2026
Castello di Volpaia
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.

Hotels with pools and free breakfast in Chianti Region

4-star hotels with pools in Chianti Region

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.

Top Chianti Region Hotel Reviews

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