Title: Chianti Region Vacation Home Rentals from CA $184: Search Top Private Vacation Homes for Rent | 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) # Chianti Region Vacation Rentals - ![](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 [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four 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) ## Browse Select Chianti Region Vacation Homes ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/43000000/42410000/42405100/42405029/3584552d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/43000000/42410000/42405100/42405029/313690ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/43000000/42410000/42405100/42405029/56f95cbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 Bedroom, Kitchenette (Iris)](https://images.trvl-media.com/lodging/43000000/42410000/42405100/42405029/eb2dffec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Castellina in Chianti 9.4/10 Exceptional (9) "Very nice agriturismo. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ruth [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Agriturismo-La-Ferrozzola.h42405029.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/90000000/89680000/89671500/89671431/9841f1ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/90000000/89680000/89671500/89671431/0d9c3cd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/90000000/89680000/89671500/89671431/b303672f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/90000000/89680000/89671500/89671431/4885bdd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Toscana 9.8/10 Exceptional (82) "The hostess Sonia was fabulous." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kim CA $227 CA $377 total includes taxes & fees Nov 29 - Nov 30 [](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Country-House-With-Garden.h89671431.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/84000000/83590000/83580400/83580374/f52ea845.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83590000/83580400/83580374/77d8ad70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/84000000/83590000/83580400/83580374/de85b0c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, stovetop, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/84000000/83590000/83580400/83580374/a27ccb6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Barberino Tavarnelle 9.8/10 Exceptional (9) "Great food in the area. Beautiful church tour and a fantastic host for our stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Craig & Conny M. CA $241 CA $342 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Vrbo-Property.h83580374.Hotel-Information) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/113000000/112480000/112477800/112477726/d6cca00c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/113000000/112480000/112477800/112477726/943e57af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112480000/112477800/112477726/e1a1ee18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/113000000/112480000/112477800/112477726/901e36a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Poggibonsi 10/10 Exceptional (2) "Pros: Tutto stupendo la casa la posizione è. La dolcezza della proprietaria" ![Italy](https://a.travel-assets.com/egds/marks/flags/it.svg) Anonymous traveller CA $128 CA $184 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Poggibonsi-Hotels-Holiday-Home-Piccolo-Angolo-Di-Tranquillita-With-Private-Garden-And-Wi-Fi.h112477726.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106010000/106004000/106003929/fdf431ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/107000000/106010000/106004000/106003929/279906cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/107000000/106010000/106004000/106003929/df47a6bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/107000000/106010000/106004000/106003929/9d75a9e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Certaldo 10/10 Exceptional (1) "Pros: Die familiäre Aufnahme und Unterstützung war sehr angenehm." ![Germany](https://a.travel-assets.com/egds/marks/flags/de.svg) Anonymous traveller CA $187 CA $271 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Certaldo-Hotels-Holiday-Home-Sandra-House-With-Private-Garden-And-Wi-Fi.h106003929.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/90000000/89670000/89668500/89668415/7e5ff4f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/90000000/89670000/89668500/89668415/8e529ae6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/90000000/89670000/89668500/89668415/8ebe355e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/90000000/89670000/89668500/89668415/ff32dcb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Toscana 9.8/10 Exceptional (74) "Great property, well equipped, nice views, well maintained, very friendly and helpful host. We did really enjoy our stay :-)" ![Germany](https://a.travel-assets.com/egds/marks/flags/de.svg) Robert M. CA $227 CA $377 total includes taxes & fees Nov 29 - Nov 30 [](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Apartment-House-With-Garden-Tuscany-Chianti.h89668415.Hotel-Information) ![Fireplace](https://images.trvl-media.com/lodging/97000000/96690000/96687900/96687854/b8cd1c20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96690000/96687900/96687854/c6f9f60f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96690000/96687900/96687854/cce3a55c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96690000/96687900/96687854/02d60594.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Greve in chianti 9.4/10 Exceptional (3) "Cons: Das direkt neben an 2 Hunde den ganzen Tag im Garten waren,die nicht kompatibel waren.Unsere Hunde mussten dann drinnen oder an die Leine. Das hat unseren Urlaub sehr stressig gemacht,und wir hätten es nicht gebucht wenn wir das gewusst hätten.Spühlmaschine schon länger kaputt. Etwas mehr Geschirr wär schön." ![Germany](https://a.travel-assets.com/egds/marks/flags/de.svg) Anonymous traveller CA $249 CA $325 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Pet-Friendly-Holiday-Home-Poggio-Al-Mandorlo-With-Garden.h96687854.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/28000000/27470000/27461900/27461842/72d49276.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27470000/27461900/27461842/567a5988.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/28000000/27470000/27461900/27461842/bea6b45a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/28000000/27470000/27461900/27461842/4eeaf647.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Monteriggioni 10/10 Exceptional (12) "Monteriggioni is the perfect location between Siena, San Gimignani, and roads to Chianti. The hosts Marcela, Enzo, and Alessandro really made us feel at home and comfortable. The property is beautiful, quiet, with unforgettable sunsets! Time at the pool is refreshing and relaxing, with beautiful views of the surrounding countryside. The authentic Italian kitchen was perfect for creating your own breakfasts and dinners. The bathrooms with showers have all you need, and the beds are really... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel D. CA $393 CA $559 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Monteriggioni-Hotels-Pleasant-Characteristic-Hayloft-That-Has-Been-Renovated-Into-Holiday-Apartment-In-A-Part-Of-The-Chianti-That-Is-Ideal-For-Visiting-The-Most-Important-Towns.h27461842.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/103000000/102120000/102118900/102118895/fca48803.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/103000000/102120000/102118900/102118895/6411ce97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102120000/102118900/102118895/a14ec7ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/103000000/102120000/102118900/102118895/df9c256a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Castelnuovo Berardenga CA $673 CA $854 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-Vacation-Home-Casalino-With-Shared-Pool.h102118895.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/118000000/117300000/117295700/117295627/35096bf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117300000/117295700/117295627/5196db78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/118000000/117300000/117295700/117295627/c8ec2ebf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117300000/117295700/117295627/f4379ae4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Rignano sull'Arno CA $202 CA $205 total includes taxes & fees Nov 26 - Nov 27 [](https://www.expedia.ca/Rignano-SullArno-Hotels-Holiday-Home-Felciolina-With-Mountain-View.h117295627.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/96000000/95540000/95538700/95538644/f59aa4a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/96000000/95540000/95538700/95538644/b1e3c029.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/96000000/95540000/95538700/95538644/11255409.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95540000/95538700/95538644/b52c5319.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Certaldo - Firenze CA $195 CA $357 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Certaldo-Hotels-Lendroit-Du-Coeur-En-Toscane.h95538644.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/79000000/78590000/78589900/78589849/6d595859.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/79000000/78590000/78589900/78589849/fa147b1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/79000000/78590000/78589900/78589849/a777a816.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/79000000/78590000/78589900/78589849/fb2ca589.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in BARBERINO TAVARNELLE 10/10 Exceptional (1) "Das Objekt liegt zwischen Florenz und Siena umgeben von Olivenbäumen. Die Lage ist perfekt für Ausflüge." ![Germany](https://a.travel-assets.com/egds/marks/flags/de.svg) Ramona S. CA $404 CA $508 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Apartment-Vernaccia-Country-House-Agriturismo-With-Pool.h78589849.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/58000000/57420000/57418500/57418406/da8174fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/58000000/57420000/57418500/57418406/9e3fc13d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/58000000/57420000/57418500/57418406/a42cd3ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/58000000/57420000/57418500/57418406/a37c5e38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Pian di Sco CA $208 CA $290 total includes taxes & fees Nov 26 - Nov 27 [](https://www.expedia.ca/Castelfranco-Piandisco-Hotels-Independent-Quadruple-Room.h57418406.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/118000000/117790000/117789600/117789522/0921cae9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117790000/117789600/117789522/a132a77a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, bidet, towels, soap](https://images.trvl-media.com/lodging/118000000/117790000/117789600/117789522/3571762f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117790000/117789600/117789522/1b5f1373.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Montespertoli CA $161 CA $195 total includes taxes & fees Nov 28 - Nov 29 [](https://www.expedia.ca/Montespertoli-Hotels-Vrbo-Property.h117789522.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/36000000/35780000/35773400/35773392/f3d94be9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/36000000/35780000/35773400/35773392/c8a44fa0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/36000000/35780000/35773400/35773392/652658c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/36000000/35780000/35773400/35773392/faaf4135.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in MONTERIGGIONI 10/10 Exceptional (1) "We absolutely loved Marcella & Enzo’s property. The pool was exactly what we needed to relax after a busy and hot few days in Rome & Venice. Just a 10 min drive from the train station. The home is set up very nicely with the 2 bedrooms and 2 bathrooms. We loved meeting the donkeys, having a quiet place to relax along with modern conveniences like a washing machine. We were treated like family. We hope to return in the future. Huge thank you! Breathtaking views. The cottage was picture perfect. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $437 CA $692 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Monteriggioni-Hotels-Apart-Charm.h35773392.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/118000000/117880000/117875500/117875443/7ce71ecc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117880000/117875500/117875443/2ea3e2b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, bidet, towels](https://images.trvl-media.com/lodging/118000000/117880000/117875500/117875443/ee869150.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117880000/117875500/117875443/70e917ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Montevarchi CA $185 CA $240 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Montevarchi-Hotels-Between-Florence.h117875443.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165667/76bfb3d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165667/699bdc9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165667/58c48d22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165667/9f41201d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Montespertoli CA $225 CA $228 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Montespertoli-Hotels-Villa-Il-Frantoio-With-Shared-Pool.h78165667.Hotel-Information) ![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/98000000/97110000/97106600/97106560/ccf584f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/98000000/97110000/97106600/97106560/b2a2fe01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, bidet, towels](https://images.trvl-media.com/lodging/98000000/97110000/97106600/97106560/f3ec922c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/98000000/97110000/97106600/97106560/e9760d65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Impruneta CA $117 CA $218 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Impruneta-Hotels-House-With-Separate-Entrance-At-The-Gates-Of-Florence-And-Chianti.h97106560.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/91000000/90020000/90018800/90018709/1c393c70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90020000/90018800/90018709/7a051a0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/91000000/90020000/90018800/90018709/83c89340.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90020000/90018800/90018709/9b8da1dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Laterina 10/10 Exceptional (1) "Bella struttura inun borgo medievale tranquillo proprietari presenti e simpatici giardino tenuto perfettamente consigliato" ![Italy](https://a.travel-assets.com/egds/marks/flags/it.svg) Luca G. CA $802 CA $1,003 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Pergine-Valdarno-Hotels-Holiday-Home-Altrove-With-Private-Pool.h90018709.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/48000000/47030000/47026200/47026113/727fddb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/48000000/47030000/47026200/47026113/38560b1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/48000000/47030000/47026200/47026113/8963b952.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/48000000/47030000/47026200/47026113/bbfe6d56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Impruneta CA $16,234 CA $18,104 total includes taxes & fees Nov 28 - Nov 29 [](https://www.expedia.ca/Impruneta-Hotels-A-Luxury-Villa-ON-THE-Hills-OF-Florence.h47026113.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=2025-12-07&endDate=2025-12-08®ionId=603148&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AA_BF_PROMO_603148) ![](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-Private-Vacation-Homes.d603148-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChianti-Region-Private-Vacation-Homes.d603148-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Chianti Region Hotel Reviews ![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) ![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) ![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) ![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) ![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) ![Hotel Toscana Ambassador](https://images.trvl-media.com/lodging/2000000/1430000/1429500/1429488/7717f75b_y.jpg) ### Hotel Toscana Ambassador 10/10 Excellent "Excellent emplacement pour explorer la région. Facile de se trouver un stationnement gratuit en face de l'hôtel. Chambre propre, mais relativement sans charme, plutôt impersonnelle côté déco, mais tout ce dont on a besoin y est toutefois, donc je recommande si vous cherchez qqchose d'efficace, abordable et fonctionnel. Le déjeuner buffet est très bon!" [](https://expedia.ca/Poggibonsi-Hotels-Hotel-Toscana-Ambassador.h1429488.Hotel-Information) ## Find out more about Chianti Region ## Chianti Region Vacation Homes information | Number of reviews | 107 | | --- | --- | | Accommodation | 462 Vacation Homes | | Lowest Price | CA $184 | | Highest Price | CA $18,104 | ## 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) - [Luxury Hotels in Castellina in Chianti](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Luxury-Hotel.0-0-d55534-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Hotel Wedding Venues Hotels in Castellina in Chianti](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Wedding-Hotels.0-0-d55534-tWeddingHotels.Travel-Guide-Filter-Hotels) - 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[Things to do in Greve in Chianti](https://www.expedia.ca/Things-To-Do-In-Greve-In-Chianti.d601773.Travel-Guide-Activities) - [Things to do in Lecchi in Chianti](https://www.expedia.ca/Things-To-Do-In-Lecchi-In-Chianti.d553248635974650979.Travel-Guide-Activities) - [Things to do in Panzano in Chianti](https://www.expedia.ca/Things-To-Do-In-Panzano-In-Chianti.d602564.Travel-Guide-Activities) - [Book Vacation Homes in Chianti Region on Expedia.it](https://www.expedia.it/Regione-Del-Chianti-Case-Vacanze-Private.d603148-aaCaseVacanzePrivate.Guida-Viaggi-Alloggi)