Title: Book the Best Chianti Region WINERY Hotels in 2026 | 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) ![Torre del Mangia](https://images.trvl-media.com/place/6077928/93b26497-cd9b-4b10-a397-2800e342e418.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Chianti Region from CA $78 - ![](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 Winery Hotels Tonight [Dec 3 - Dec 4](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-12-03&endDate=2025-12-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 4 - Dec 5](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-12-04&endDate=2025-12-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chianti Region Winery Hotels ![Exterior detail](https://images.trvl-media.com/lodging/11000000/10510000/10507800/10507728/34e550c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily buffet breakfast (EUR 20 per person)](https://images.trvl-media.com/lodging/11000000/10510000/10507800/10507728/4bb934b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/11000000/10510000/10507800/10507728/23f04f21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room](https://images.trvl-media.com/lodging/11000000/10510000/10507800/10507728/6fcc8f08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Art Hotel Villa Agape Oltrarno 9.8/10 Exceptional (1002) "Great hotel with amazing gardens and Italian environment, beautiful!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Servando CA $185 CA $226 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Florence-Hotels-Art-Hotel-Villa-Agape.h10507728.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/11eaf7f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/d6216ebc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/c3101a79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/84f971b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Certosa di Pontignano Castelnuovo Berardenga 9.6/10 Exceptional (502) "Excellent place to stay even for the next time. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Xuejie CA $65 CA $78 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-La-Certosa-Di-Pontignano.h9797642.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/3000000/2540000/2530300/2530284/29ec8453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 2 Bedrooms, Patio (6 Adults) | Living room](https://images.trvl-media.com/lodging/3000000/2540000/2530300/2530284/11fad22b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/3000000/2540000/2530300/2530284/93f882ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/3000000/2540000/2530300/2530284/e2d371ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Borgo di Pietrafitta Relais Castellina in Chianti 9.4/10 Exceptional (169) "Wonderful setting." ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Simon CA $152 CA $174 total includes taxes & fees Jan 2 - Jan 3, 2026 [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Borgo-Di-Pietrafitta-Relais.h2530284.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/37000000/36330000/36326000/36325942/819a9035.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite Deluxe | View from room](https://images.trvl-media.com/lodging/37000000/36330000/36326000/36325942/b41e8535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite 1 Bedroom | Private kitchen](https://images.trvl-media.com/lodging/37000000/36330000/36326000/36325942/28b23c5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite Deluxe | View from room](https://images.trvl-media.com/lodging/37000000/36330000/36326000/36325942/e4c153b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Capanna Suites Montalcino 9.8/10 Exceptional (130) "Absolutely amazing resort with amazing staff and service. Great food and beautiful spa experience. Highly reccommend anyone going to Tuscany to book here - you will not be disappointed ! " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Megan [](https://www.expedia.ca/Montalcino-Hotels-Capanna-Suites.h36325942.Hotel-Information) ![Garden views, open daily](https://images.trvl-media.com/lodging/1000000/920000/913600/913526/e7798301.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Room](https://images.trvl-media.com/lodging/1000000/920000/913600/913526/08a3f239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/920000/913600/913526/d9d2a48e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, Annex Building (stair access only) | Private kitchen](https://images.trvl-media.com/lodging/1000000/920000/913600/913526/8e79fd5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Globus Urban Hotel Historic Centre of Florence 9.4/10 Exceptional (1057) "We stayed in the apartment and loved everything about it!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Aran CA $153 CA $192 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Florence-Hotels-Globus-Urban-Hotel.h913526.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) ![Tasting room](https://images.trvl-media.com/lodging/3000000/2540000/2537900/2537801/fe1302e8.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 (89) "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) ![Borgo Suite with private garden | Terrace/patio](https://images.trvl-media.com/lodging/2000000/1210000/1206900/1206900/ceb71ffc.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) ![Breakfast, lunch, dinner served; Italian cuisine, garden views ](https://images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/9f05cf5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/d71aded7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/70f4f37a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic Suite, Vineyard View | Vineyard view](https://images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/91065266.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castello di Fonterutoli Wine Resort Castellina in Chianti 9.4/10 Exceptional (198) "Clean room, courteous staff, and good winery" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sangchun CA $211 CA $239 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Castello-Di-Fonterutoli.h5172395.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) ![Rooftop terrace](https://images.trvl-media.com/lodging/97000000/96090000/96089000/96088992/1b3e0ef4.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) ![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) ### 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 $120 CA $138 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Casa-Di-Palaia.h96088992.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2530000/2524500/2524406/c72d4869.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; garden views](https://images.trvl-media.com/lodging/3000000/2530000/2524500/2524406/02c2ebd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite](https://images.trvl-media.com/lodging/3000000/2530000/2524500/2524406/079c3c2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; garden views](https://images.trvl-media.com/lodging/3000000/2530000/2524500/2524406/d6061fdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relais Poggio Borgoni San Casciano in Val di Pesa 9.8/10 Exceptional (57) "Very personal, kind & sympathatic Staff. The Place is gorgeous." ![Switzerland](https://a.travel-assets.com/egds/marks/flags/ch.svg) Nils CA $143 CA $164 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Relais-Poggio-Borgoni.h2524406.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=2025-12-17&endDate=2025-12-18®ionId=603148&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Chianti Region Hotel Reviews ![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 hotel and services exceeded my expectations." [](https://expedia.ca/Barberino-Tavarnelle-Hotels-Hotel-Borgo-Di-Cortefreda-Relais.h1216478.Hotel-Information) ![Hotel Toscana Ambassador](https://images.trvl-media.com/lodging/2000000/1430000/1429500/1429488/7717f75b_y.jpg) ### Hotel Toscana Ambassador 10/10 Excellent "We recommend the Toscana Ambassador to everyone, as we had a great experience with its cleanliness, hospitality, friendliness, and an extraordinary breakfast, with excellent service from Ada & Julia and the rest of the crew, from the front desk to room service. If you ever visit Poggibonsi, Tuscany, stay here with no hesitation. " [](https://expedia.ca/Poggibonsi-Hotels-Hotel-Toscana-Ambassador.h1429488.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 "Amazing experience! The staff were very knowledgeable and helpful in setting up our dinner and wine tour. Room had a beautiful view. This was the best part of our journey through Italy. Keep up the great work! A+ " [](https://expedia.ca/Castellina-In-Chianti-Hotels-Castello-Di-Fonterutoli.h5172395.Hotel-Information) ![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) ![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) ![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) ![Il Borro - Relais & Châteaux](https://images.trvl-media.com/lodging/6000000/5590000/5585700/5585638/4a6bd899_y.jpg) ### Il Borro - Relais & Châteaux 10/10 Excellent "A one of a kind, unique property amazing cuisine, and the tour we took of the wine cellar was the best I have ever experienced thanks to the helpfulness and knowledge of our guide Sophia" [](https://expedia.ca/Loro-Ciuffenna-Hotels-Il-Borro-Relais-Chateaux.h5585638.Hotel-Information) ![Park Hotel Chianti](https://images.trvl-media.com/lodging/2000000/1410000/1402100/1402089/9fa8e1be_y.jpg) ### Park Hotel Chianti 10/10 Excellent "Lovely hotel in Chianti, staff were outstanding! 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