Title: Castellina in Chianti Villas from CA $244 | Expedia.ca [Castellina in Chianti Travel Guide](https://expedia.ca/Castellina-In-Chianti.dx55534)[Hotels in Castellina in Chianti](https://expedia.ca/Castellina-In-Chianti-Hotels.d55534.Travel-Guide-Hotels)[Vacation Rentals in Castellina in Chianti](https://expedia.ca/Castellina-In-Chianti-Vacation-Rentals.d55534.Travel-Guide-VacationRentals)[Flights to Castellina in Chianti](https://expedia.ca/Cheap-Flights-To-Castellina-In-Chianti.d55534.Travel-Guide-Flights)[Castellina in Chianti Car Rentals](https://expedia.ca/Car-Rentals-In-Castellina-In-Chianti.d55534.Car-Rental-Guide)[Castellina in Chianti Vacation Packages](https://expedia.ca/Castellina-In-Chianti.d55534.Destination-Travel-Guides) ![Castellina in Chianti showing heritage architecture, religious elements and a church or cathedral](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/157000/157304-Tuscany.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Castellina in Chianti Villa Rentals from CA $244 ![](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 Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=55534&startDate=2025-10-31&endDate=2025-11-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=55534&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=55534&startDate=2025-11-21&endDate=2025-11-23&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=55534&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Castellina in Chianti Villas ![Exterior detail](https://images.trvl-media.com/lodging/34000000/33090000/33086300/33086208/7dd4167e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/34000000/33090000/33086300/33086208/79ded7ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/34000000/33090000/33086300/33086208/b96fa96e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/34000000/33090000/33086300/33086208/cf57554c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25 Careggi Rifredi 10/10 Exceptional (1) "Staff went over and above for us. Food was wonderful service 5 stars" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) robert g. CA $15,493 CA $15,493 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Florence-Hotels-VILLA-MEDICEA-Seven-Bedroom-Villa.h33086208.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/6112d62c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/28509faf.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) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/df76d7aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28 Gaiole in Chianti CA $9,683 CA $10,497 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-CHIANTIGAIO-Fourteen-Bedroom-Villa.h33066451.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/111000000/110140000/110132300/110132299/7f0bb06d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/111000000/110140000/110132300/110132299/360bcf7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Spa](https://images.trvl-media.com/lodging/111000000/110140000/110132300/110132299/63f2ab21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/111000000/110140000/110132300/110132299/7c521815.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Dei Pavoni - Luxury Villa on top of hills in Florence Toscana 10/10 Exceptional (1) "The host was amazing! The property was beautiful. All was seamless! All of our needs were met. Highly recommend! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leopard I. CA $2,900 CA $3,313 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Bagno-A-Ripoli-Hotels-Villa-Dei-Pavoni-Luxury-Villa-On-Top-Of-Hills-In-Florence.h110132299.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/28000000/27130000/27125200/27125149/d88438f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![](https://images.trvl-media.com/lodging/28000000/27130000/27125200/27125149/w745h499x12y7-5d6f59fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, in-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/28000000/27130000/27125200/27125149/31ed4590.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27130000/27125200/27125149/cc6f8d82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### panoramica casa con piscina privata siena 7.0/10 Good (10) "We had a lovely stay and the hosts were warm, accommodating and responsive. The location is incredible -- extensive views from both sides of the property; the hilltop village setting is out of a postcard with lovely little streets and nooks to explore; and the local shops, market days, restaurants provide everything needed locally. The property is adequate, a little rustic, but well suited to time outdoors by the lovely pool and as a springboard for day trips throughout amazing Tuscany.... ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Olivier B. CA $132 CA $244 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Chiusdino-Hotels-Panoramica-Casa-Con-Piscina-Privata.h27125149.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/87000000/86500000/86496800/86496746/c9dc3be7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/87000000/86500000/86496800/86496746/4214b7a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/87000000/86500000/86496800/86496746/bd7589fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/87000000/86500000/86496800/86496746/1f150e3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Tuscan home between Florence & Siena Florence 10/10 Exceptional (6) "From the moment we entered to our last day everything was perfect. Group of 15 and we all fit comfortably. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Debra P. CA $1,797 CA $2,796 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Beautiful-Tuscan-Home-Between-Florence-Siena.h86496746.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165677/9188e7e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, table tennis](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165677/419c09ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![7 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165677/6703c11a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Milani with Shared Pool, Private Terrace & Wi-Fi Montespertoli 10/10 Exceptional (1) "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 $2,143 CA $2,147 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Montespertoli-Hotels-Villa-Milani-With-Shared-Pool.h78165677.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/100000000/99440000/99430700/99430681/5d1ad91c.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) ![5 bedrooms, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/100000000/99440000/99430700/99430681/c44dc7fb.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 'La Petrosa' with Private Pool, Private Garden and Balcony Radda in Chianti 10/10 Exceptional (1) "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 $1,826 CA $2,865 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Radda-In-Chianti-Hotels-Villa-La-Petrosa-With-Private-Pool.h99430681.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/33000000/32590000/32584300/32584249/495a2b82.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) ![9 bedrooms, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/33000000/32590000/32584300/32584249/e3cae5da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!! Montespertoli 10/10 Exceptional (12) "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 $2,034 CA $2,330 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Montespertoli-Hotels-Luxury.h32584249.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/113000000/112080000/112078800/112078745/c7d590be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![9 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112080000/112078800/112078745/608550a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, dishwasher](https://images.trvl-media.com/lodging/113000000/112080000/112078800/112078745/02b896e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/113000000/112080000/112078800/112078745/ea41bd7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### VILLA SOLATA - Nine Bedroom Villa, Sleeps 20 Siena CA $2,905 CA $2,905 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Bucine-Hotels-VILLA-SOLATA-Nine-Bedroom-Villa.h112078745.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/106000000/105600000/105595300/105595286/55c68f22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace, books](https://images.trvl-media.com/lodging/106000000/105600000/105595300/105595286/29c05483.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace, books](https://images.trvl-media.com/lodging/106000000/105600000/105595300/105595286/d02d90eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, cookware/dishes/utensils](https://images.trvl-media.com/lodging/106000000/105600000/105595300/105595286/2610e960.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Il Signorino GREVE IN CHIANTI 10/10 Exceptional (2) "Nice place 👌 " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Avi A. CA $498 CA $711 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Vrbo-Property.h105595286.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) ![6 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99790000/99787300/99787239/f89f6ede.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99790000/99787300/99787239/5448a085.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/100000000/99790000/99787300/99787239/ba66cbc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning Rignano sull'Arno 7.0/10 Good (2) "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 $2,540 CA $3,440 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Rignano-SullArno-Hotels-Villa-Il-Frassine-With-Private-Pool.h99787239.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/116000000/115910000/115909300/115909202/129066f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic Villa, Hill View | Living area](https://images.trvl-media.com/lodging/116000000/115910000/115909300/115909202/61a9caf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic Villa, Hill View | Living area](https://images.trvl-media.com/lodging/116000000/115910000/115909300/115909202/9a3a96a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115910000/115909300/115909202/a408caff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wine Apartments Florence Lawrence Scandicci CA $65 CA $445 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Scandicci-Hotels-Wine-Apartments-Florence-Lawrence.h115909202.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/90000000/89590000/89589300/89589245/1654ecb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89590000/89589300/89589245/0ac9183c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/90000000/89590000/89589300/89589245/f9f06ea3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/90000000/89590000/89589300/89589245/24ff1535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa "Il Fornacino" with Pool, Garden & Wi-Fi Rapolano Terme 9.0/10 Wonderful (4) "Wonderful house. Big, cool even with 36 degrees outside. Very Nice swimming pool with shaddow places if needed. Very friendly and helpfull host." ![Netherlands](https://a.travel-assets.com/egds/marks/flags/nl.svg) Toon M. CA $794 CA $1,197 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Rapolano-Terme-Hotels-Villa-Il-Fornacino-With-Pool.h89589245.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/19000000/18780000/18773500/18773430/47b129c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18780000/18773500/18773430/afd50901.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18780000/18773500/18773430/e94bf161.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/19000000/18780000/18773500/18773430/3d6f9205.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Villa in the Florentine hills Florence 9.8/10 Exceptional (143) "Beautiful property and great experience " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) edward p. CA $570 CA $819 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Florence-Hotels-Luxury-Villa-In-The-Florentine-Hills.h18773430.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106400000/106395500/106395493/bee6bf59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106400000/106395500/106395493/bd4b3a9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106400000/106395500/106395493/7d23d3c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106400000/106395500/106395493/6623ebf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casa dei Renai by Rentbeat Signa CA $82 CA $404 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Signa-Hotels-Casa-Dei-Renai-By-Rentbeat.h106395493.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) ![Smart TV, books](https://images.trvl-media.com/lodging/91000000/90190000/90189600/90189550/af3ef658.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) ![Interior](https://images.trvl-media.com/lodging/91000000/90190000/90189600/90189550/1424f3bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country House with heated pool near the center Careggi Rifredi 9.4/10 Exceptional (10) "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 $488 CA $781 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Florence-Hotels-Romantic-Villa-With-Private-Pool-Near-The-Center.h90189550.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/106000000/105350000/105347600/105347550/792b75e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/106000000/105350000/105347600/105347550/8516acc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105350000/105347600/105347550/2a6c678e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105350000/105347600/105347550/af826b95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### "A Casa di Franca Villa con piscina" Gambassi Terme 10/10 Exceptional (1) "Pros: La estancia en la casa fue muy bonita. Estaba cerca de Florencia, Siena, Sant Gimigano, etc. Viajamos toda la familia y los propietarios fueron muy acogedores. La piscina es un sitio perfecto para relajarse y bañarse después de ver la Toscana. Nuestros hijos y sobrinos jugaron porque tenían de todo. La casa muy equipada y limpia con televisión en todas las habitaciones. Los propietarios además nos ayudaron con un pequeño contratiempo que tuvimos. Nos sentimos como en casa, muchas... ![Spain](https://a.travel-assets.com/egds/marks/flags/es.svg) Anonymous traveller CA $595 CA $1,196 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Gambassi-Terme-Hotels-A-Casa-Di-Franca-Villa-Nel-Chianti-With-Private-Pool.h105347550.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83210000/83207300/83207211/f2af4ebd.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/84000000/83210000/83207300/83207211/41d8a81a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83210000/83207300/83207211/61b3ffc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/84000000/83210000/83207300/83207211/34f96c14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### "Villa Erbolino" with Private Garden, Outdoor Stone Bathtub & Wi-Fi Gaiole in Chianti 10/10 Exceptional (7) "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 $1,000 CA $1,039 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Villa-Erbolino-With-Private-Garden.h83207211.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/115000000/114250000/114245500/114245407/f1f06d14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114250000/114245500/114245407/9081825d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/115000000/114250000/114245500/114245407/c3bcd9af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/115000000/114250000/114245500/114245407/76f44bf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC Radda in Chianti 8.0/10 Very good (1) "We spent a great family time at Adme’s house.The house has everything. Was very clean and well maintained . Will highly recommend." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ana r. CA $1,055 CA $2,099 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Radda-In-Chianti-Hotels-4-Bedroom-Stonehouse-With-Stunning-Pool-In-The-Chianti-Countryside-With-WiFi.h114245407.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108280000/108275300/108275238/w1166h830x2y0-085ca741.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108280000/108275300/108275238/w1166h835x2y0-8d015ca6.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/w1168h860x1y0-67cae5a7.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) ### Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~ Impruneta 10/10 Exceptional (3) "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 $487 CA $640 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Impruneta-Hotels-Vrbo-Property.h108275238.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=2025-11-09&endDate=2025-11-10®ionId=55534&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](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%2FCastellina-In-Chianti-Villas.d55534-aaVillas.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FCastellina-In-Chianti-Villas.d55534-aaVillas.Travel-Guide-Accommodation) ## Top Castellina in Chianti Hotel Reviews ![Solo Experience Hotel](//images.trvl-media.com/lodging/3000000/2540000/2533900/2533892/2466c367_y.jpg) ### Solo Experience Hotel 10/10 Excellent "This hotel is in a great location, very walkable to all the sites and restaurants. We didn't hear any noise from the market nearby or other hotel guests. Rachel the attendant at breakfast is AMAZING and made our stay even better. I would highly recommend this hotel and would stay again if I'm in Florence." [](https://expedia.ca/Florence-Hotels-Solo-Experience-Hotel.h2533892.Hotel-Information) ![Hotel De La Ville](//images.trvl-media.com/lodging/1000000/30000/21500/21408/85f0ef28_y.jpg) ### Hotel De La Ville 10/10 Excellent "Excellent. Friendly staff." [](https://expedia.ca/Florence-Hotels-Hotel-De-La-Ville.h21408.Hotel-Information) ![Bernini Palace](//images.trvl-media.com/lodging/1000000/20000/14000/13999/84743cc7_y.jpg) ### Bernini Palace 10/10 Excellent "Lovely property very conveniently situated " [](https://expedia.ca/Florence-Hotels-Bernini-Palace.h13999.Hotel-Information) ![The Social Hub Florence Belfiore](//images.trvl-media.com/lodging/111000000/110560000/110551000/110550930/66ceba72_y.jpg) ### The Social Hub Florence Belfiore 10/10 Excellent "Easy airport shuttle." [](https://expedia.ca/Florence-Hotels-The-Social-Hub-Florence-Belfiore.h110550930.Hotel-Information) ![Hotel Delle Nazioni](//images.trvl-media.com/lodging/1000000/930000/920200/920176/dd1e8db6_y.jpg) ### Hotel Delle Nazioni 10/10 Excellent "Great location. Next to train station. Nice room. Breakfast was good too. Definitely going to stay again here in Florence. " [](https://expedia.ca/Florence-Hotels-Hotel-Delle-Nazioni.h920176.Hotel-Information) ![IQ Hotel Firenze](//images.trvl-media.com/lodging/90000000/89040000/89035100/89035039/72f32f77_y.jpg) ### IQ Hotel Firenze 10/10 Excellent "Lovely building. Convenient location. Staff excellent. Room very comfortable." [](https://expedia.ca/Florence-Hotels-IQ-Hotel-Firenze.h89035039.Hotel-Information) ![Grand Hotel Baglioni](//images.trvl-media.com/lodging/1000000/10000/6400/6371/849fb031_y.jpg) ### Grand Hotel Baglioni 10/10 Excellent "A lovely hotel full of rich history! We thoroughly enjoyed our stay. The rooftop restaurant and terrace have amazing city views which added to the magic." [](https://expedia.ca/Florence-Hotels-Grand-Hotel-Baglioni.h6371.Hotel-Information) ![The Social Hub Florence Lavagnini](//images.trvl-media.com/lodging/24000000/23200000/23198300/23198289/fdc60d68_y.jpg) ### The Social Hub Florence Lavagnini 10/10 Excellent "Great hotel with wonderful staff and breakfast." [](https://expedia.ca/Florence-Hotels-The-Social-Hub-Florence-Lavagnini.h23198289.Hotel-Information) ![The Market Urban Hotel](//images.trvl-media.com/lodging/1000000/110000/108100/108028/7e915af7_y.jpg) ### The Market Urban Hotel 10/10 Excellent "Great location with very clean room. Breakfast was great with pastries, fruit, eggs and efficient staff." [](https://expedia.ca/Florence-Hotels-The-Market-Urban-Hotel.h108028.Hotel-Information) ## Find out more about Castellina in Chianti ## Castellina in Chianti Villas information | Number of reviews | 145 | | --- | --- | | Accommodation | 2117 Villas | | Lowest Price | CA $244 | | Highest Price | CA $15,493 | ## Frequently asked questions ### How much do villas in Castellina in Chianti cost? > Villas in Castellina in Chianti range between CA $244 and CA $15,493 per night. These stays offer the privacy of your own space at a price that doesn't break the bank. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply. ### How many villas are there in Castellina in Chianti? > You can choose from 2117 villas in Castellina in Chianti. No matter if you're traveling with the family or planning a getaway with your buddies, Expedia will help you find the ideal base for your squad. ### Why book your villa in Castellina in Chianti with Expedia? > Reserving a villa in Castellina in Chianti is as simple as deciding on your travel dates and picking the option suited to your needs. In search of something affordable or luxurious, or a property that also has a kitchen and laundry? Use Expedia's search filters to narrow your results and find the perfect pad. ### How can I find cheap villas in Castellina in Chianti? > The easiest way to compare cheap villas in Castellina in Chianti is with Expedia's convenient filter tool. Narrow your search by amenities, budget and star rating to nab awesome rates in only a few clicks. ### What is there to do near my villa in Castellina in Chianti? > Whatever your interests, Castellina in Chianti has loads to keep you on the hop. [Buondonno Winery](https://www.expedia.ca/Buondonno-Winery-Castellina-in-Chianti.d553248635823420151.Vacation-Attraction), [City Hall Castellina In Chianti](https://www.expedia.ca/City-Hall-Castellina-In-Chianti-Castellina-in-Chianti.d553248635175258965.Vacation-Attraction) and [Casa Vinicola Luigi Cecchi](https://www.expedia.ca/Casa-Vinicola-Luigi-Cecchi-Castellina-in-Chianti.d6103262.Vacation-Attraction) are on most visitors' itineraries. Don't forget to explore [Walls of Monteriggioni](https://www.expedia.ca/Walls-Of-Monteriggioni-Castellina-in-Chianti.d553248621532497696.Vacation-Attraction), [Castellina Fortress](https://www.expedia.ca/Castellina-Fortress-Castellina-in-Chianti.d715302045798678528.Vacation-Attraction) and [Archaeological Museum of Chianti](https://www.expedia.ca/Archaeological-Museum-Of-Chianti-Castellina-in-Chianti.d553248621533001050.Vacation-Attraction) either. With Expedia's Castellina in Chianti hotel deals, you can discover even more terrific attractions like these with the cash you save. ## Explore a world of travel with Expedia - More ways to book - [Book Villas in Castellina in Chianti on Expedia.it](https://www.expedia.it/Castellina-In-Chianti-Ville.d55534-aaVille.Guida-Viaggi-Alloggi)