Title: Book the Best Hotels with POOL in Chianti Region in 2025 | Expedia.ca [Chianti Region Travel Guide](https://expedia.ca/Chianti-Region.dx603148)[Hotels in Chianti Region](https://expedia.ca/Chianti-Region-Hotels.d603148.Travel-Guide-Hotels)[Vacation Rentals in Chianti Region](https://expedia.ca/Chianti-Region-Vacation-Rentals.d603148.Travel-Guide-VacationRentals)[Flights to Chianti Region](https://expedia.ca/Cheap-Flights-To-Chianti-Region.d603148.Travel-Guide-Flights)[Things to do in Chianti Region](https://expedia.ca/Things-To-Do-In-Chianti-Region.d603148.Travel-Guide-Activities)[Chianti Region Car Rentals](https://expedia.ca/Car-Rentals-In-Chianti-Region.d603148.Car-Rental-Guide)[Chianti Region Vacation Packages](https://expedia.ca/Chianti-Region.d603148.Destination-Travel-Guides) ![Chianti Region showing farmland](https://images.trvl-media.com/place/603148/a6b4be95-df3f-44a2-bf6d-bb1e6f500def.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Chianti Region - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Chianti Region Hotels with a Pool Tonight [Nov 19 - Nov 20](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-11-19&endDate=2025-11-20&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 20 - Nov 21](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-11-20&endDate=2025-11-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-11-21&endDate=2025-11-23&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-11-28&endDate=2025-11-30&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chianti Region Hotels with a Pool ![Seasonal outdoor pool, open 9:00 AM to 7:00 PM, sun loungers](https://images.trvl-media.com/lodging/2000000/1140000/1131000/1130942/6055a736.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Steam room, Turkish bath, body scrubs, massages](https://images.trvl-media.com/lodging/2000000/1140000/1131000/1130942/e763d814.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/2000000/1140000/1131000/1130942/0dc1dfcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1140000/1131000/1130942/b50d05a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Cassia di Baccano Loro Ciuffenna 9.4/10 Exceptional (23) "The staff were great and the villa was amazing" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ralphvincent CA $177 CA $195 total includes taxes & fees Nov 21 - Nov 22 [](https://www.expedia.ca/Loro-Ciuffenna-Hotels-Villa-Cassia-Di-Baccano.h1130942.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/97000000/96090000/96089000/96088992/e4040fa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive Studio Suite, 1 Bedroom, Hot Tub, Garden View](https://images.trvl-media.com/lodging/97000000/96090000/96089000/96088992/b9a4ef80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/97000000/96090000/96089000/96088992/aa5161f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool views ](https://images.trvl-media.com/lodging/97000000/96090000/96089000/96088992/bf1b9609.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casa di Palaia Greve in Chianti 10/10 Exceptional (22) "Very well located in the heart if the Tuscany region." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eli CA $122 CA $140 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Casa-Di-Palaia.h96088992.Hotel-Information) ![Seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/3000000/2540000/2537900/2537801/089cca52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/3000000/2540000/2537900/2537801/095c274a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Winery](https://images.trvl-media.com/lodging/3000000/2540000/2537900/2537801/cbeec78c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Duplex, 1 Bedroom, Patio | Private kitchenette](https://images.trvl-media.com/lodging/3000000/2540000/2537900/2537801/8aeb24c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castello di Meleto Gaiole in Chianti 8.8/10 Excellent (87) "Super clean.. walked in can smell how clean it was. Beautiful location only down side restaurant was close and it was very difficult finding food around on a Monday afternoon. Wine tour is a must had a great time small group but wonderful people.. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Castello-Di-Meleto.h2537801.Hotel-Information) ![Seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/3000000/2730000/2723600/2723529/169b7345.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/3000000/2730000/2723600/2723529/4c3be6b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/3000000/2730000/2723600/2723529/a7b1b268.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room](https://images.trvl-media.com/lodging/3000000/2730000/2723600/2723529/37f63acd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa il Fedino San Casciano in Val di Pesa 9.6/10 Exceptional (97) "We had a wonderfull welcome, very professional ,friendly and helpful in every aspect. Great villa with Tuscany vibe and breathtaking views.Close enough to Florence.You can't ask for better. We will return again." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Mario CA $206 CA $234 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Villa-Il-Fedino.h2723529.Hotel-Information) ![Seasonal outdoor pool, open 9:00 AM to 7:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1220000/1216500/1216478/288cff0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room](https://images.trvl-media.com/lodging/2000000/1220000/1216500/1216478/4222355a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; local cuisine, garden views ](https://images.trvl-media.com/lodging/2000000/1220000/1216500/1216478/346cd924.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; local cuisine, garden views ](https://images.trvl-media.com/lodging/2000000/1220000/1216500/1216478/ac1776a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Borgo di Cortefreda Relais Barberino Tavarnelle 9.4/10 Exceptional (474) "The views were spectacular and the grounds were so peaceful" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle CA $115 CA $137 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Hotel-Borgo-Di-Cortefreda-Relais.h1216478.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/36000000/35380000/35371400/35371398/cf423eb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/36000000/35380000/35371400/35371398/96573fa9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/36000000/35380000/35371400/35371398/4208eeb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/36000000/35380000/35371400/35371398/e16b396d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Resort 37 Rignano sull'Arno 9.8/10 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](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathy CA $306 CA $341 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Rignano-SullArno-Hotels-Resort-37.h35371398.Hotel-Information) ![Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/3000000/2550000/2540800/2540748/5edc5b37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/3000000/2550000/2540800/2540748/4cc4dd78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/3000000/2550000/2540800/2540748/8fc9f594.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2550000/2540800/2540748/37ac4429.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Colle Etrusco Salivolpi Castellina in Chianti 9.6/10 Exceptional (111) "Beautiful relaxing property. We wish we had more time to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wendi CA $140 CA $159 total includes taxes & fees Nov 26 - Nov 27 [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Hotel-Colle-Etrusco-Salivolpi.h2540748.Hotel-Information) ![Indoor pool, seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1290000/1289200/1289163/187ae210.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Buffet](https://images.trvl-media.com/lodging/2000000/1290000/1289200/1289163/0273c2c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/2000000/1290000/1289200/1289163/b8b0f4e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mansarda](https://images.trvl-media.com/lodging/2000000/1290000/1289200/1289163/bb8071f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Palazzo San niccolò & Spa Radda in Chianti 9.2/10 Wonderful (175) "Ideal country setting" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Dee [](https://www.expedia.ca/Radda-In-Chianti-Hotels-Hotel-Palazzo-San-Niccolo.h1289163.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/91000000/90770000/90767900/90767811/fe55fe49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90770000/90767900/90767811/56ba2c57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/91000000/90770000/90767900/90767811/c2b795f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/91000000/90770000/90767900/90767811/d9818c3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casale La Gora Figline e Incisa Valdarno 9.6/10 Exceptional (21) "Casale La Gora in Tuscany. The property is beautifully renovated, blending historic charm with modern architecture. Our room was clean and cozy, the breakfast was delicious, and the pool was perfect for cooling off during the hot summer days. The host was warm, friendly, and always helpful, which made our stay even more enjoyable. We would definitely love to come back! " ![Sweden](https://a.travel-assets.com/egds/marks/flags/se.svg) Besarta CA $130 CA $147 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Figline-E-Incisa-Valdarno-Hotels-Casale-La-Gora.h90767811.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1210000/1206900/1206900/0a0d67ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1210000/1206900/1206900/a7babbcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/2000000/1210000/1206900/1206900/6123c69c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Chapel](https://images.trvl-media.com/lodging/2000000/1210000/1206900/1206900/df15c8c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castello di Tornano Wine Resort Gaiole in Chianti 9.0/10 Wonderful (100) "Loved our stay here! It was so pretty and the staff was amazing! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacquelyn [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Castello-Di-Tornano.h1206900.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-03&endDate=2025-12-04®ionId=603148&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Chianti Region Hotel Reviews ![Hotel Palazzo San Lorenzo & SPA](https://images.trvl-media.com/lodging/4000000/3480000/3475000/3474921/1af45070_y.jpg) ### Hotel Palazzo San Lorenzo & SPA 10/10 Excellent "Beautiful hotel and spa. Excellent amenities and modern luxuries. " [](https://expedia.ca/Colle-Di-Val-DElsa-Hotels-Hotel-Palazzo-San-Lorenzo-SPA.h3474921.Hotel-Information) ![Castello di Fonterutoli Wine Resort](https://images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/9f05cf5a_y.jpg) ### Castello di Fonterutoli Wine Resort 10/10 Excellent "Clean room, courteous staff, and good winery" [](https://expedia.ca/Castellina-In-Chianti-Hotels-Castello-Di-Fonterutoli.h5172395.Hotel-Information) ![Villa I Barronci Resort & Spa](https://images.trvl-media.com/lodging/3000000/2530000/2523800/2523750/d7de1ccd_y.jpg) ### Villa I Barronci Resort & Spa 10/10 Excellent "Stayed here as part of our honeymoon. Staff were super helpful with reservations and recommendations. The view is beautiful and the rooms are cozy. The breakfast was delicious as well." [](https://expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Villa-I-Barronci-Resort-Spa.h2523750.Hotel-Information) ![Hotel Borgo di Cortefreda Relais](https://images.trvl-media.com/lodging/2000000/1220000/1216500/1216478/288cff0c_y.jpg) ### Hotel Borgo di Cortefreda Relais 10/10 Excellent "The staff at the front desk was amazing. When we arrived he greeted us with such a warm smile and welcomed us to the hotel. He absolutely made the hotel experience much better. " [](https://expedia.ca/Barberino-Tavarnelle-Hotels-Hotel-Borgo-Di-Cortefreda-Relais.h1216478.Hotel-Information) ![Villa Castiglione](https://images.trvl-media.com/lodging/2000000/1350000/1348200/1348125/dbdc1d6b_y.jpg) ### Villa Castiglione 10/10 Excellent "Nice and cute place. Great price. " [](https://expedia.ca/Impruneta-Hotels-Villa-Castiglione.h1348125.Hotel-Information) ![COMO Castello Del Nero](https://images.trvl-media.com/lodging/2000000/1280000/1279800/1279768/5908bcb2_y.jpg) ### COMO Castello Del Nero 10/10 Excellent "Wonderful stay. 5-stars across the board if you’re looking for disconnecting and relaxing in the rolling hills of the Tuscan countryside. Easy day/dinner trips to Florence or Siena (rental car). " [](https://expedia.ca/Barberino-Tavarnelle-Hotels-COMO-Castello-Del-Nero.h1279768.Hotel-Information) ![Hotel Certaldo](https://images.trvl-media.com/lodging/2000000/1680000/1675500/1675499/0f881b23_y.jpg) ### Hotel Certaldo 10/10 Excellent "Beautiful garden in the back" [](https://expedia.ca/Certaldo-Hotels-Hotel-Certaldo.h1675499.Hotel-Information) ![Castello di Spaltenna- Small Luxury Hotels of the World](https://images.trvl-media.com/lodging/3000000/2550000/2540800/2540741/75ac6194_y.jpg) ### Castello di Spaltenna- Small Luxury Hotels of the World 10/10 Excellent "The breakfast was fresh with lots of options and a outdoor setting on the property. The property is beautiful, pool area and spa so peaceful. Excellent service in all areas of hotel! " [](https://expedia.ca/Gaiole-In-Chianti-Hotels-Castello-Di-Spaltenna.h2540741.Hotel-Information) ![Hotel Villa Cesi](https://images.trvl-media.com/lodging/1000000/980000/976900/976828/dbde33dc_y.jpg) ### Hotel Villa Cesi 10/10 Excellent "We had a wonderful stay." 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