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

Find Hotels with a Pool in Chianti Region

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Our top choices for Chianti Region hotels with a pool

1. Belvedere di San Leonino

Belvedere di San Leonino
4.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (211 reviews)
  • cleanliness
    Scenic Tuscan escape with a poolside paradise and winery at your doorstep.
$102 nightly
The price is $119
Oct 28 - Oct 29
Total with taxes and fees
Belvedere di San Leonino

2. Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa
4.0 star property
Radda in Chianti
9.2 out of 10, Wonderful, (305 reviews)
  • cleanliness
    Sun-kissed pools in tuscan splendor beckon with historic charm and breathtaking views.
$104 nightly
The price is $121
Nov 23 - Nov 24
Total with taxes and fees
Palazzo Leopoldo Dimora Storica & Spa

3. Castello di Tornano Wine Resort

Castello di Tornano Wine Resort
Gaiole in Chianti
9.2 out of 10, Wonderful, (139 reviews)
  • cleanliness
    Poolside bliss awaits at this Tuscan wine resort where medieval castle meets vineyard views.
$152 nightly
The price is $176
Oct 29 - Oct 30
Total with taxes and fees
Castello di Tornano Wine Resort

4. La pietra del cabreo

La pietra del cabreo
Greve in Chianti
10.0 out of 10, Exceptional, (144 reviews)
  • cleanliness
    Dive into the seasonal outdoor pool with breathtaking views at this beautifully maintained rural bed & breakfast.
$172 nightly
The price is $194
Oct 30 - Oct 31
Total with taxes and fees
La pietra del cabreo

5. Hotel Villa Campomaggio

Hotel Villa Campomaggio
4.0 star property
Radda in Chianti
9.4 out of 10, Exceptional, (195 reviews)
  • cleanliness
    Soak in mountain views from the sun-drenched outdoor pool at this Tuscan retreat where spa treatments and regional cuisine await.
$149 nightly
The price is $170
Oct 28 - Oct 29
Total with taxes and fees
Hotel Villa Campomaggio

6. Borgo Del Cabreo

Borgo Del Cabreo
Greve in Chianti
10.0 out of 10, Exceptional, (288 reviews)
  • cleanliness
    Tuscan retreat with seasonal outdoor pool offers vineyard views and winery experiences.
$183 nightly
The price is $206
Oct 28 - Oct 29
Total with taxes and fees
Borgo Del Cabreo

7. 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, (530 reviews)
  • cleanliness
    Discover a Tuscan oasis with a seasonal pool sanctuary, loungers for sunbathing, and poolside drinks service in wine country.
$106 nightly
The price is $123
Nov 27 - Nov 28
Total with taxes and fees
Hotel Borgo di Cortefreda Relais - Place of Charme

8. Castello Vicchiomaggio

Castello Vicchiomaggio
Greve in Chianti
9.4 out of 10, Exceptional, (443 reviews)
  • cleanliness
    Refreshing infinity pool with breathtaking views awaits at this charming Tuscan farm stay with winery.
$178 nightly
The price is $196
Oct 29 - Oct 30
Total with taxes and fees
Castello Vicchiomaggio

9. 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.
$77 nightly
The price is $91
Nov 26 - Nov 27
Total with taxes and fees
Hotel Palazzo San niccolò & Spa

10. Dievole Wine Resort

Dievole Wine Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (218 reviews)
  • cleanliness
    Splash into luxury at a Tuscan wine resort with two outdoor pools and vineyard views.
$247 nightly
The price is $281
Nov 21 - Nov 22
Total with taxes and fees
Dievole Wine Resort
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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