Title: Chianti Region Villas from CA $129 | 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) ![Typical Tuscany stone house with vineyard in the Chianti region and magical sunset,Tuscany,Italy,Europe; Shutterstock ID 230998399](https://images.trvl-media.com/place/603148/f55ed247-c704-412c-bed7-4bc776c30e02.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/603148/f55ed247-c704-412c-bed7-4bc776c30e02.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 prices for these dates In two weeks [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chianti Region villas ![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108280000/108275300/108275238/38e5a789.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/109000000/108280000/108275300/108275238/w1166h863x2y0-ddee714e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/109000000/108280000/108275300/108275238/w1166h854x2y0-790f85bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/109000000/108280000/108275300/108275238/w1166h857x2y0-a94584e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Impruneta [](https://www.expedia.ca/Impruneta-Hotels-Vrbo-Property.h108275238.Hotel-Information) 10/10 Exceptional (3 reviews) "Pictures do not do it justice, this house and location is absolutely beautiful. Very comfortable beds, clean house, beauty views, nice fireplace.owner goes above and beyond to make you feel welcome. She had her local wine, cooked us a delishes breakfast, and also brought her olive oil to do tasting. We will definitely be back, i thank you for an amazing experience and a beautiful house." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lidija M. CA $561 CA $737 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Impruneta-Hotels-Vrbo-Property.h108275238.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/100000000/99440000/99430700/99430681/b8286297.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99440000/99430700/99430681/03ae69bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/100000000/99440000/99430700/99430681/b2bb8dfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/100000000/99440000/99430700/99430681/513cbcf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Radda in Chianti [](https://www.expedia.ca/Radda-In-Chianti-Hotels-Villa-La-Petrosa-With-Private-Pool.h99430681.Hotel-Information) 10/10 Exceptional (1 review) "Pros: Świetna lokalizacja i przyjemne otoczenie domu. Dom położony na wzniesieniu z którego roztaczał się piękny widok. Cons: Osoba opiekująca się domem nie mówiła po angielsku co utrudniało komunikację. Nie byliśmy świadomi że dom podzielony jest na 2 części góra i piwnica w której były dodatkowe 3 pokoje. Uszkodzona pralka która nie dopierała pranych ubrań - brudna woda z zanieczyszczeniami które dodatkowo brudziły ubrania." ![Poland](https://a.travel-assets.com/egds/marks/flags/pl.svg) Anonymous traveller CA $2,834 CA $3,865 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Radda-In-Chianti-Hotels-Villa-La-Petrosa-With-Private-Pool.h99430681.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/dcfa042c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/afb73a16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/25aedd65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/782eb623.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Gaiole in Chianti [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-CHIANTIGAIO-Fourteen-Bedroom-Villa.h33066451.Hotel-Information) CA $9,602 CA $10,409 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-CHIANTIGAIO-Fourteen-Bedroom-Villa.h33066451.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/123000000/122490000/122488700/122488659/c92c20b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122490000/122488700/122488659/aa63342e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122490000/122488700/122488659/76c1c946.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/123000000/122490000/122488700/122488659/b48487ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Colle Val D'Elsa [](https://www.expedia.ca/Colle-Di-Val-DElsa-Hotels-VILLA-ALTAMIRA-Eighteen-Bedroom-Villa.h122488659.Hotel-Information) CA $19,043 CA $19,043 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Colle-Di-Val-DElsa-Hotels-VILLA-ALTAMIRA-Eighteen-Bedroom-Villa.h122488659.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/124000000/123670000/123669300/123669271/c3424e32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/124000000/123670000/123669300/123669271/368811a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/124000000/123670000/123669300/123669271/ecc6720f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/124000000/123670000/123669300/123669271/8b48796e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Castellina in Chianti [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Viniard-Villa-Residence-Le-Rose-In-Chianti.h123669271.Hotel-Information) CA $516 CA $1,061 total includes taxes & fees Jan 23 - Jan 24 [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Viniard-Villa-Residence-Le-Rose-In-Chianti.h123669271.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/77000000/76780000/76771500/76771413/w1920h1279x0y1-a132bf6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![9 bedrooms, free WiFi](https://images.trvl-media.com/lodging/77000000/76780000/76771500/76771413/0a5c24e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76780000/76771500/76771413/w1920h1157x0y1-ed6e0399.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/77000000/76780000/76771500/76771413/bc5dd1c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Castellina in Chianti [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-VILLA-IL-PRINCIPE-Nine-Bedroom-Villa.h76771413.Hotel-Information) CA $7,586 CA $8,392 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-VILLA-IL-PRINCIPE-Nine-Bedroom-Villa.h76771413.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/34000000/33960000/33956800/33956712/a34e800d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33960000/33956800/33956712/a26a2615.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor banquet area](https://images.trvl-media.com/lodging/34000000/33960000/33956800/33956712/52fb9f8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool, sun loungers](https://images.trvl-media.com/lodging/34000000/33960000/33956800/33956712/65e72921.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in impruneta [](https://www.expedia.ca/Impruneta-Hotels-Tailored-To-YouVilla-Wheated-Pool-And-Concierge-Only-8-Mile-To-Florence-Center.h33956712.Hotel-Information) 10/10 Exceptional (106 reviews) "The Villa and grounds are absolutely beautiful! Caterina and her family members were the most gracious hosts. They could not do enough to make sure we had a "once in a lifetime" multi-generational family trip and truly made us feel like part of their family during our stay. We loved every second of our time in Tuscany and would highly recommend this amazing property." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Charles S. CA $1,861 CA $2,133 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Impruneta-Hotels-Tailored-To-YouVilla-Wheated-Pool-And-Concierge-Only-8-Mile-To-Florence-Center.h33956712.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165677/1e6c21a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, table tennis](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165677/c326d5ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165677/9fd29a0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165677/2fd0fef1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Montespertoli [](https://www.expedia.ca/Montespertoli-Hotels-Villa-Milani-With-Shared-Pool.h78165677.Hotel-Information) 10/10 Exceptional (1 review) "The Villa was charming and absolutely bursting with character. We loved exploring the house and the grounds! It was quiet and relaxing, but still only a short drive from Florence, Sienna, San Gimignano and other favorite towns of Tuscany. A memorable stay in an absolutely unique villa!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Scott M. CA $2,585 CA $2,589 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Montespertoli-Hotels-Villa-Milani-With-Shared-Pool.h78165677.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/87000000/86500000/86496800/86496746/bd7589fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![7 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/87000000/86500000/86496800/86496746/8f497170.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/87000000/86500000/86496800/86496746/57f40b13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/87000000/86500000/86496800/86496746/87d9fa0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Florence [](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Beautiful-Tuscan-Home-Between-Florence-Siena.h86496746.Hotel-Information) 10/10 Exceptional (7 reviews) "Judy was amazing and very helpfulNothing to do with the property, but I sure you pre book all nights out/transportation" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Frank V. CA $1,046 CA $1,932 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Beautiful-Tuscan-Home-Between-Florence-Siena.h86496746.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/33000000/32590000/32584300/32584249/w2189h1640x4y5-0fbf58c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/33000000/32590000/32584300/32584249/517571bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/33000000/32590000/32584300/32584249/87c073f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/33000000/32590000/32584300/32584249/51bd2610.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Montespertoli [](https://www.expedia.ca/Montespertoli-Hotels-Luxury.h32584249.Hotel-Information) 10/10 Exceptional (12 reviews) "Amazing Property! The house was impeccably clean, with spacious bedrooms and comfortable beds. Our gracious host Nicola spoiled us with his generosity. He went beyond our expectations to ensure that our stay was perfect. He and his wife welcomed us with a delicious homemade apple cake. He drove us to the nearby town of Montespertoli to pick-up groceries and provisions. He recommended a local chef to cook for us at the villa. The meal was amazing and memorable. We will be back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elise D. CA $2,066 CA $2,359 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Montespertoli-Hotels-Luxury.h32584249.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/84000000/83210000/83207300/83207211/81953563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83210000/83207300/83207211/ae2c6602.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83210000/83207300/83207211/0e2eec35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/84000000/83210000/83207300/83207211/a822b4f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Gaiole in Chianti [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Villa-Erbolino-With-Private-Garden.h83207211.Hotel-Information) 10/10 Exceptional (8 reviews) "Country location but easy access to a great local winery/restaurant and the town of Gaiole." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) russ h. CA $1,678 CA $1,716 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Villa-Erbolino-With-Private-Garden.h83207211.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292182/9dbd198e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292182/99750750.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292182/59636b41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292182/09f4ffea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Vico dʼArbia [](https://www.expedia.ca/Siena-Hotels-Villa-Capannina-With-Private-Pool.h123292182.Hotel-Information) CA $1,554 CA $1,714 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Siena-Hotels-Villa-Capannina-With-Private-Pool.h123292182.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/32000000/31540000/31539100/31539094/06053989.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/32000000/31540000/31539100/31539094/682c69f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/32000000/31540000/31539100/31539094/08415ea8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/32000000/31540000/31539100/31539094/37bf79c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Montespertoli [](https://www.expedia.ca/Montespertoli-Hotels-Luxury-Villa-With-Swimmingpool-In-Chianti-Sleeps-22-Large-Groups.h31539094.Hotel-Information) 10/10 Exceptional (38 reviews) "Excellent in every way. Highly recommend" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ed M. CA $2,098 CA $2,396 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Montespertoli-Hotels-Luxury-Villa-With-Swimmingpool-In-Chianti-Sleeps-22-Large-Groups.h31539094.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292187/7dec8a2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292187/e3bba8c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292187/2e9c5263.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor banquet area](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292187/717cdd46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Vico dʼArbia [](https://www.expedia.ca/Siena-Hotels-Villa-Torre-Among-The-Hills-Of-Siena.h123292187.Hotel-Information) CA $2,190 CA $2,350 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Siena-Hotels-Villa-Torre-Among-The-Hills-Of-Siena.h123292187.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99790000/99787300/99787239/60af890d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/100000000/99790000/99787300/99787239/eabd8042.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99790000/99787300/99787239/f69f21a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/100000000/99790000/99787300/99787239/912c9501.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Rignano sull'Arno [](https://www.expedia.ca/Rignano-SullArno-Hotels-Villa-Il-Frassine-With-Private-Pool.h99787239.Hotel-Information) 7.0/10 Good (2 reviews) "We arrived after dark, tired from long overnight flight. We had no water pressure upstairs and no hot water anywhere. This was corrected the next day. One on-suite toilette would not flush properly and leaked at the grinder motor. A "tech" was called in. He informed us that he could not fix it, they would need to call someone else. When we continued to report the issue to the host, she informed us that the "tech" said it was working OK. The "tech" informed us that it was not but he could not fix... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Norman C. CA $3,741 CA $4,633 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Rignano-SullArno-Hotels-Villa-Il-Frassine-With-Private-Pool.h99787239.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/115000000/114510000/114506600/114506575/5657bedf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114510000/114506600/114506575/a5994ef5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114510000/114506600/114506575/24bd1fb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/115000000/114510000/114506600/114506575/538ab53b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Tavarnelle Val di Pesa [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Villa-Virgilio-Colline-Del-Chianti-With-Mountain-View.h114506575.Hotel-Information) CA $1,754 CA $2,187 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Villa-Virgilio-Colline-Del-Chianti-With-Mountain-View.h114506575.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292181/798e008d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292181/b1163ba5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292181/1b3afdb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292181/571a61ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Vico dʼArbia [](https://www.expedia.ca/Siena-Hotels-Villa-Capanna-A-Window-Onto-Tuscany.h123292181.Hotel-Information) CA $2,190 CA $2,350 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Siena-Hotels-Villa-Capanna-A-Window-Onto-Tuscany.h123292181.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/27000000/26500000/26500000/26499959/8208f9d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Triple Room | Bathroom](https://images.trvl-media.com/lodging/27000000/26500000/26500000/26499959/c721d6f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/27000000/26500000/26500000/26499959/4f173bce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/27000000/26500000/26500000/26499959/e04fd69c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Foiano della Chiana [](https://www.expedia.ca/Foiano-Della-Chiana-Hotels-Agriturismo-Artisti-Del-Cavallo.h26499959.Hotel-Information) 8.4/10 Very good (24 reviews) "Good house for one night. " ![Germany](https://a.travel-assets.com/egds/marks/flags/de.svg) Heiner CA $114 CA $129 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Foiano-Della-Chiana-Hotels-Agriturismo-Artisti-Del-Cavallo.h26499959.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/d6476b51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/a8ccbf55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/d05582b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/8099b959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Sinalunga [](https://www.expedia.ca/Sinalunga-Hotels-Il-Poggio-Delleremita.h27448054.Hotel-Information) 10/10 Exceptional (59 reviews) "Fantastic place! Great location. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Paul Q. CA $240 CA $275 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Sinalunga-Hotels-Il-Poggio-Delleremita.h27448054.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/91000000/90190000/90189600/90189550/6c7fa5e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, a heated pool](https://images.trvl-media.com/lodging/91000000/90190000/90189600/90189550/fe208c77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90190000/90189600/90189550/1424f3bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/91000000/90190000/90189600/90189550/27af464f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Careggi Rifredi [](https://www.expedia.ca/Florence-Hotels-Romantic-Villa-With-Private-Pool-Near-The-Center.h90189550.Hotel-Information) 9.4/10 Exceptional (10 reviews) "The property was outstanding and our family had a blast. It was a nice get away from the crowds in the city to enjoy the animals and greenery of the house on the farm. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nancy P. CA $484 CA $775 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Florence-Hotels-Romantic-Villa-With-Private-Pool-Near-The-Center.h90189550.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=2026-02-01&endDate=2026-02-02®ionId=603148&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Villas [](https://www.expedia.ca/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy®ionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-04-18&d1=2026-04-18&endDate=2026-04-21&d2=2026-04-21&lodging=VILLA) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy®ionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-04-18&d1=2026-04-18&endDate=2026-04-21&d2=2026-04-21&lodging=APARTMENT) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy®ionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-04-18&d1=2026-04-18&endDate=2026-04-21&d2=2026-04-21&lodging=APART_HOTEL) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy®ionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-04-18&d1=2026-04-18&endDate=2026-04-21&d2=2026-04-21&lodging=VACATION_HOME) Residences [](https://www.expedia.ca/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy®ionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-04-18&d1=2026-04-18&endDate=2026-04-21&d2=2026-04-21&lodging=RESIDENCE) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy®ionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-04-18&d1=2026-04-18&endDate=2026-04-21&d2=2026-04-21&lodging=COTTAGE) Condos [](https://www.expedia.ca/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy®ionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-04-18&d1=2026-04-18&endDate=2026-04-21&d2=2026-04-21&lodging=CONDO) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy®ionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-04-18&d1=2026-04-18&endDate=2026-04-21&d2=2026-04-21&lodging=CABIN) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy®ionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-04-18&d1=2026-04-18&endDate=2026-04-21&d2=2026-04-21&lodging=CHALET) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChianti-Region-Villas.d603148-aaVillas.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChianti-Region-Villas.d603148-aaVillas.Travel-Guide-Accommodation) ## Top Chianti Region Hotel Reviews ![Villa Casagrande Resort & SPA](https://images.trvl-media.com/lodging/1000000/900000/891700/891661/f41faf16_y.jpg) ### Villa Casagrande Resort & SPA 10/10 Excellent "Always beautiful when I stay here, staff are helpful and every room clean and tidy " [](https://expedia.ca/Figline-E-Incisa-Valdarno-Hotels-Villa-Casagrande-Resort-SPA.h891661.Hotel-Information) ![Hotel Palazzo San niccolò & Spa](https://images.trvl-media.com/lodging/2000000/1290000/1289200/1289163/b8b0f4e2_y.jpg) ### Hotel Palazzo San niccolò & Spa 10/10 Excellent "One of the best hotels I’ve visited! " [](https://expedia.ca/Radda-In-Chianti-Hotels-Hotel-Palazzo-San-Niccolo.h1289163.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 "Livia was amazing and made me feel very welcomed. She has great customer service skills and showed me where places were on the map. The room and bathroom was spacious." [](https://expedia.ca/Colle-Di-Val-DElsa-Hotels-Hotel-Palazzo-San-Lorenzo-SPA.h3474921.Hotel-Information) ![Villa San Lucchese](https://images.trvl-media.com/lodging/2000000/1690000/1685900/1685892/f05836b4_y.jpg) ### Villa San Lucchese 10/10 Excellent "Beautiful place Great service " [](https://expedia.ca/Poggibonsi-Hotels-Villa-San-Lucchese.h1685892.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 "Very clean,staff was very kind and helpful. Looking forward to come back! 😊" [](https://expedia.ca/Castellina-In-Chianti-Hotels-Castello-Di-Fonterutoli.h5172395.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 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) ![Salvadonica - Borgo del Chianti](https://images.trvl-media.com/lodging/21000000/20490000/20484000/20483959/56ce48bb_y.jpg) ### Salvadonica - Borgo del Chianti 10/10 Excellent "Great staff, great room and amenities. Outstanding romantic Tuscany location. Going back again." [](https://expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Salvadonica.h20483959.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) ## Find out more about Chianti Region ## Chianti Region Villas information | Number of reviews | 234 | | ----------------- | ---------- | | Accommodation | 571 Villas | | Lowest Price | CA $129 | | Highest Price | CA $10,409 | ## Frequently asked questions ### How much do villas in Chianti Region cost? ### How many villas are there in Chianti Region? ### Why book your villa in Chianti Region with Expedia? ### How can I find cheap villas in Chianti Region? ### What is there to do near my villa in Chianti Region? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [Badia Coltibuono Hotels ](https://www.expedia.ca/Badia-Coltibuono-Hotels.d553248635975857717.Travel-Guide-Hotels) - [Casole Hotels ](https://www.expedia.ca/Casole-Hotels.d3000429476.Travel-Guide-Hotels) - [B&B in Castellina in Chianti ](https://www.expedia.ca/Castellina-In-Chianti-Bed-And-Breakfast.d55534-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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