Find Hotels with a Pool in Chianti Region

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Check availability on Chianti Region Hotels with a Pool

Top Chianti Region Hotels with a Pool

Outdoor pool, open 8 AM to 8:30 PM, pool umbrellas, sun loungers
Salvadonica - Borgo del Chianti

Salvadonica - Borgo del Chianti

San Casciano in Val di Pesa
  • Outdoor pool
  • Pool loungers
9.6 out of 10, Exceptional, (256)
Poolside paradise awaits at this Tuscan retreat where sun-drenched loungers and umbrellas border the refreshing outdoor pool. Bicycles for countryside exploration, an on-site winery, and delicious local cuisine complete the idyllic escape.
$105 nightly
The price is $120
Nov 11 - Nov 12
Total with taxes and fees
Salvadonica - Borgo del Chianti
Seasonal outdoor pool, open 9:00 AM to 7:00 PM, sun loungers
Villa Cassia di Baccano

Villa Cassia di Baccano

Loro Ciuffenna
  • Poolside bar
  • Pool loungers
  • Full-service spa
9.4 out of 10, Exceptional, (23)
Poolside bliss defines summer days at this countryside retreat, where seasonal swimming delights both adults and children. Villa Cassia di Baccano elevates the experience with massage services and a convenient bar serving refreshing drinks under the Italian sun.
$134 nightly
The price is $148
Nov 18 - Nov 19
Total with taxes and fees
Villa Cassia di Baccano
Seasonal outdoor pool
Castello Vicchiomaggio

Castello Vicchiomaggio

Greve in Chianti
  • Pool
  • Parking included
  • Free WiFi
  • Restaurant
  • Housekeeping
  • Soundproof rooms
9.4 out of 10, Exceptional, (370)
Seasonal pool waters reflect stunning countryside vistas while guests savor exceptional regional cuisine from the on-site restaurant. Wine enthusiasts delight in tasting room experiences, winery tours, and special release events at this serene, picturesque retreat.
Castello Vicchiomaggio
Exterior
Casa di Palaia

Casa di Palaia

Greve in Chianti
  • Pool
  • Breakfast included
  • Free WiFi
  • Restaurant
  • Air conditioning
  • Housekeeping
10.0 out of 10, Exceptional, (22)
Seasonal swimming delights await at this lakeside guesthouse where private in-room pools complement the outdoor swimming area. Casa di Palaia's restaurant serves meals best enjoyed on the rooftop terrace before exploring nearby hiking trails.
$90 nightly
The price is $104
Dec 9 - Dec 10
Total with taxes and fees
Casa di Palaia
Seasonal outdoor pool
Castello La Leccia

Castello La Leccia

Castellina in Chianti
  • Full-service spa
10.0 out of 10, Exceptional, (93)
Sparkling waters await at the seasonal pool, open May through September on this charming Italian farm stay. After swimming, guests can explore nearby hiking trails, enjoy complimentary bicycles, or unwind in the sauna.
$219 nightly
The price is $245
Nov 11 - Nov 12
Total with taxes and fees
Castello La Leccia
Outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas, sun loungers
Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa

4.0 star property
San Casciano in Val di Pesa
  • Outdoor pool
  • Poolside bar
  • Pool loungers
  • Hot tub
9.2 out of 10, Wonderful, (408)
Poolside paradise beckons with loungers and umbrellas surrounding the tranquil outdoor oasis. Guests savor Italian cuisine at the adjacent restaurant or refreshing drinks from the bar while soaking in mountain vistas after spa treatments.
$88 nightly
The price is $103
Nov 16 - Nov 17
Total with taxes and fees
Villa I Barronci Resort & Spa
Exterior
Il Borro - Relais & Châteaux

Il Borro - Relais & Châteaux

Loro Ciuffenna
  • Poolside bar
  • Pool loungers
9.2 out of 10, Wonderful, (96)
Mountain biking trails, horseback riding, and tennis courts surround a seasonal pool with loungers and refreshing drinks from the poolside bar. Spa services, winery tours, and 2 restaurants complete this Tuscan farm stay experience.
$417 nightly
The price is $459
Dec 8 - Dec 9
Total with taxes and fees
Il Borro - Relais & Châteaux
Outdoor pool, sun loungers
Castello di Tornano Wine Resort

Castello di Tornano Wine Resort

Gaiole in Chianti
  • Outdoor pool
  • Pool loungers
9.0 out of 10, Wonderful, (100)
Seasonal swimming awaits at this Tuscan farm stay, where sun loungers border the refreshing outdoor pool. Beyond aquatic relaxation, guests discover an attached winery, tennis court, and complimentary breakfast buffet amid Castle of Brolio's enchanting landscape.
$161 nightly
The price is $187
Nov 21 - Nov 22
Total with taxes and fees
Castello di Tornano Wine Resort
Seasonal outdoor pool, open 9:00 AM to 7:00 PM, pool umbrellas
Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais

4.0 star property
Barberino Tavarnelle
  • Poolside bar
  • Pool loungers
  • Full-service spa
9.4 out of 10, Exceptional, (473)
Sparkling waters await at the seasonal outdoor pool, complete with comfortable loungers and refreshing poolside bar service. Beyond aquatic pleasures, this Tuscan retreat offers spa treatments, hiking trails, and wine tasting experiences amid stunning countryside views.
$86 nightly
The price is $101
Nov 30 - Dec 1
Total with taxes and fees
Hotel Borgo di Cortefreda Relais
Seasonal outdoor pool, sun loungers
Castello di Meleto

Castello di Meleto

Gaiole in Chianti
  • Pool loungers
8.8 out of 10, Excellent, (86)
Vibrant farm stay surrounds a seasonal outdoor pool with sun loungers set amid Tuscan vineyards. Guests can book winery tours, enjoy al fresco dining at La Fornace di Meleto, or explore nearby hiking trails before returning to air-conditioned comfort.
$145 nightly
The price is $169
Nov 10 - Nov 11
Total with taxes and fees
Castello di Meleto
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
"Clean room, courteous staff, and good winery"
Sangchun 1-night trip
Posted 4 days ago
Castello di Fonterutoli Wine Resort

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