A vineyard with rows of grapevines, a house surrounded by trees, and a road with vehicles.

Find Hotels with a Pool in Chianti Region

Check availability on Chianti Region Hotels with a Pool

Our top choices for Chianti Region hotels with a pool

1. Hotel Borgo di Cortefreda Relais - Place of Charme

Hotel Borgo di Cortefreda Relais - Place of Charme
4.0 star property
Tavarnelle Val di Pesa
9.4 out of 10, Exceptional, (532 reviews)
  • cleanliness
    Discover a Tuscan oasis with a seasonal pool sanctuary, loungers for sunbathing, and poolside drinks service in wine country.
$77 nightly
The price is $92
Dec 14 - Dec 15
Total with taxes and fees
Hotel Borgo di Cortefreda Relais - Place of Charme

2. Belvedere di San Leonino

Belvedere di San Leonino
4.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (213 reviews)
  • cleanliness
    Scenic Tuscan escape with a poolside paradise and winery at your doorstep.
$105 nightly
The price is $122
Nov 15 - Nov 16
Total with taxes and fees
Belvedere di San Leonino

3. Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa
4.0 star property
Radda in Chianti
9.2 out of 10, Wonderful, (307 reviews)
  • cleanliness
    Sun-kissed pools in tuscan splendor beckon with historic charm and breathtaking views.
$105 nightly
The price is $122
Dec 1 - Dec 2
Total with taxes and fees
Palazzo Leopoldo Dimora Storica & Spa

4. Hotel Palazzo San niccolò & Spa

Hotel Palazzo San niccolò & Spa
4.0 star property
Radda in Chianti
9.2 out of 10, Wonderful, (198 reviews)
  • cleanliness
    Dive into year-round pool perfection with indoor and seasonal outdoor swimming options at this elegant Tuscan retreat.
$72 nightly
The price is $86
Dec 1 - Dec 2
Total with taxes and fees
Hotel Palazzo San niccolò & Spa

5. Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA
4.0 star property
Figline e Incisa Valdarno
9.2 out of 10, Wonderful, (415 reviews)
  • cleanliness
    Swim through captivating seasons at this hotel with both indoor and outdoor pools, spa treatments, and an attached winery.
$97 nightly
The price is $109
Dec 13 - Dec 14
Total with taxes and fees
Villa Casagrande Resort & SPA

6. Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa
4.0 star property
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (483 reviews)
  • cleanliness
    Sip poolside bliss at this luxury Tuscan retreat where serene mountain views frame your aquatic sanctuary.
$67 nightly
The price is $81
Dec 15 - Dec 16
Total with taxes and fees
Villa I Barronci Resort & Spa

7. Dievole Wine Resort

Dievole Wine Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (219 reviews)
  • cleanliness
    Splash into luxury at a Tuscan wine resort with two outdoor pools and vineyard views.
$260 nightly
The price is $295
Nov 20 - Nov 21
Total with taxes and fees
Dievole Wine Resort

8. Castello di Volpaia

Castello di Volpaia
3.0 star property
Radda in Chianti
9.6 out of 10, Exceptional, (75 reviews)
  • cleanliness
    Escape to a countryside sanctuary with an indoor and outdoor pool surrounded by vineyard views at this historic farm stay.
$205 nightly
The price is $230
Dec 7 - Dec 8
Total with taxes and fees
Castello di Volpaia

9. Villa il Poggiale - Dimora Storica

Villa il Poggiale - Dimora Storica
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (163 reviews)
  • cleanliness
    Relax poolside at this Tuscan villa with seasonal outdoor pool, hot tub, and sun loungers.
$101 nightly
The price is $112
Dec 15 - Dec 16
Total with taxes and fees
Villa il Poggiale - Dimora Storica

10. La Locanda Volpaia

La Locanda Volpaia
Radda in Chianti
10.0 out of 10, Exceptional, (4 reviews)
$138 nightly
The price is $155
Dec 9 - Dec 10
Total with taxes and fees
La Locanda 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.

Choose what matters most at hotels with a pool in Chianti Region

Hotels with pools and free breakfast in Chianti Region

4-star hotels with pools in Chianti Region

5-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.

Find out more about Chianti Region

Discover top Chianti Region attractions

In the enchanting Chianti Region, travelers can indulge in a wealth of experiences that beautifully blend culture, culinary delights, and stunning landscapes. Start your journey with a visit to a picturesque olive grove, where you can learn about the traditional methods of olive oil production and participate in a tasting that highlights the region's rich flavors. Next, immerse yourself in the art of Tuscan cooking at a local cooking class, where a skilled chef will guide you through preparing authentic dishes using fresh, local ingredients. For wine enthusiasts, the Chianti landscape is dotted with charming vineyards offering guided tours and tastings, showcasing the renowned Chianti Classico wines. Don’t miss the opportunity to explore the quaint hilltop villages that dot the landscape, each offering unique artisan shops and breathtaking views of the rolling hills. Lastly, take a leisurely bicycle ride along the scenic countryside roads, allowing you to soak in the natural beauty and tranquility that Chianti is famous for. When it comes to accommodations, consider staying in a traditional villa surrounded by vineyards, providing you with the perfect base to explore this captivating region while enjoying the attentive service and authentic charm you deserve.

Top Chianti Region Hotel Reviews

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