Find Hotels with a Pool in Chianti Region

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Top Chianti Region Hotels with a Pool

Our top choices for Chianti Region hotels with a pool

Villa I Barronci Resort & Spa

4.0 star property
9.2 out of 10, Wonderful, (398)
"Beautiful hotel!"
$92 nightly
The price is $108
Sep 2 - Sep 3
Total with taxes and fees
Villa I Barronci Resort & Spa

Locanda le Piazze

4.0 star property
9.8 out of 10, Exceptional, (181)
"Great place to stay!! Plenty of vineyards and towns close by! "
$314 nightly
The price is $352
Sep 3 - Sep 4
Total with taxes and fees
Locanda le Piazze

Villa la Palagina

4.0 star property
9.0 out of 10, Wonderful, (335)
"The perfect Tuscan experience. We’ll located, well maintained and checked off all the boxes for us as a family and as adult couples without kids who joined us. "
$70 nightly
The price is $80
Sep 2 - Sep 3
Total with taxes and fees
Villa la Palagina

Villa Scacciapensieri Boutique Hotel

4.0 star property
9.2 out of 10, Wonderful, (406)
"Lovely traditional hotel, great pool and good food. I’ve had better breakfasts, but more than adequate to get you started in a morning. "
$256 nightly
The price is $287
Oct 1 - Oct 2
Total with taxes and fees
Villa Scacciapensieri Boutique Hotel

VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN SUITE ROOMS, SWIMMING POOL, SPA, SAUNA.

10.0 out of 10, Exceptional, (117)
"Great place to stay with family/friends. The grounds are beautiful and immaculately maintained. The house is spotless. The owners organized a meal and a cooking class at the villa for us. They were willing and able to help in any way possible and were very organized with the check in and check out process. Will definitely return. "
VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN SUITE ROOMS, SWIMMING POOL, SPA, SAUNA.

Borgo Grondaie

3.0 star property
9.6 out of 10, Exceptional, (423)
"Excellent place to stay for a relaxing weekend and enjoy the view of Siena"
$128 nightly
The price is $147
Oct 2 - Oct 3
Total with taxes and fees
Borgo Grondaie

Hotel Pescille - Tuscany Charme

3.0 star property
9.2 out of 10, Wonderful, (315)
"Amazing Hotel, great location, the room very renovated and the breakfast was amazing - we really enjoyed and recommended the hotel"
$100 nightly
The price is $118
Sep 30 - Oct 1
Total with taxes and fees
Hotel Pescille - Tuscany Charme

Villa Ermellina Siena, a Tribute Portfolio Hotel

4.0 star property
$212 nightly
The price is $240
Sep 2 - Sep 3
Total with taxes and fees
Villa Ermellina Siena, a Tribute Portfolio Hotel

Castello di Spaltenna- Small Luxury Hotels of the World

5.0 star property
9.6 out of 10, Exceptional, (250)
"This was the most authentic place I have ever seen really takes back but all the amenities by far the best place to stay in Tuscany IT Fantastic staff 5star"
$430 nightly
The price is $485
Sep 28 - Sep 29
Total with taxes and fees
Castello di Spaltenna- Small Luxury Hotels of the World

Relais Della Rovere

4.0 star property
9.0 out of 10, Wonderful, (240)
"The place was nice and quite. Close to walkable towns and neighborhoods. "
Relais Della Rovere
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

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

Find out more about Chianti Region

Booking hotels with pools in Chianti Region on Expedia

Your dream vacation is just a few clicks away thanks to Expedia's amazing selection of hotels with pools in Chianti Region. Finding them is as easy as lazing on a lounge chair thanks to the easy-to-use search wizard. All you need to do is select your dates and it'll return hundreds of fantastic options. With so many options to choose from, the filters come in handy as they let you tailor your search results based on your preferences. 

If it's luxury you're seeking, select the “5-star” filter. From infinity pools that seem to blend into the horizon to swim-up bars where you can sip on margaritas in the water, this filter will show you the most opulent accommodations available. The “guest rating” filter will help you pin down Expedia's top-rated Chianti Region hotels with a pool based on hundreds of reviews from fellow travelers. Once you've found your dream property, click through to choose your room and book. The detailed hotel descriptions on Expedia, including things like room size, cancellation policy, and info about the all-important swimming pool, means you'll know exactly what to expect when you arrive.  

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Most booked related stays in Chianti Region in 2025

Kid-friendly Chianti Region hotels with a pool

Get ready to blow up the inflatable pool floats and swimming tubes, as you'll find a multitude of kid-friendly Chianti Region hotels with a pool on Expedia. Select the “family-friendly” search filter to scan these. From splashing with mom and dad to playing around on pool noodles, your kids will love nothing more than long, sunny days in the water. Many family-friendly hotels boast children's pools with shallow water and dedicated lifeguards too, so you can rest assured your little ones are safe while playing.  

Some hotels with pools also offer kids' clubs with fun activities and events to keep your youngsters entertained all day long. They'll be able to make new friends, learn how to swim, and play classic games like water volleyball and pool tag. Best of all, with your kids kept entertained, you'll be able to enjoy some well-earned “me time”. It's worth looking for all-inclusive plans, too. These make for a hassle-free family vacation as they include all meals and drinks, so you won't have to worry about eating out or cooking. Many family-friendly hotels even offer children's menus with your kids' favorite foods.  

Chianti Region spa hotels with pools

Click both the “pool” and “spa” filters on Expedia to view some of the best Chianti Region spa hotels with pools. Picture yourself receiving a full body massage, easing the knots out of your back before diving into the refreshing water. The dreamy combination of therapeutic swimming and holistic spa treatments means you'll come back from vacation relaxed and glowing. Many hotels even offer hot tubs and wellness activities, like poolside yoga and meditation.  

Plan your pool hotel stay in Chianti Region

When looking for Chianti Region hotels with swimming pools in 2025, it's worth researching which area you'd like to stay in. You can choose to be close to key attractions or in more distant places for something more secluded. Wherever you opt for, the “popular locations” and “neighborhood” filters make it a breeze to find hotels with pools in Chianti Region's most popular areas. There are more than just hotels, too. Take advantage of the “property type” filter to view vacation homes with pools in Chianti Region, including villas, condos, and private homes.  

Top Chianti Region Hotel Reviews

Explore a world of travel with Expedia

Explore a world of travel with Expedia