Title: Chianti Region Vacation Home Rentals from CA $183: 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) ![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 [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-05-15&endDate=2026-05-17&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 vacation homes ![Front of property](https://images.trvl-media.com/lodging/43000000/42410000/42405100/42405029/df1d957c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/43000000/42410000/42405100/42405029/80b09a28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/43000000/42410000/42405100/42405029/343d0b2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/43000000/42410000/42405100/42405029/c2de7201.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Castellina in Chianti [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Agriturismo-La-Ferrozzola.h42405029.Hotel-Information) 9.4/10 Exceptional (9 reviews) "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) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/113000000/112480000/112477800/112477726/3b47f5e3.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/d6cca00c.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) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112480000/112477800/112477726/dd2a0574.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Poggibonsi [](https://www.expedia.ca/Poggibonsi-Hotels-Holiday-Home-Piccolo-Angolo-Di-Tranquillita-With-Private-Garden-And-Wi-Fi.h112477726.Hotel-Information) 10/10 Exceptional (2 reviews) "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 $183 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Poggibonsi-Hotels-Holiday-Home-Piccolo-Angolo-Di-Tranquillita-With-Private-Garden-And-Wi-Fi.h112477726.Hotel-Information) ![1 bedroom, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33680000/33675900/33675891/db850afc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33680000/33675900/33675891/4bcceb91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33680000/33675900/33675891/w4029h2268x0y0-afe178cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels, soap, shampoo](https://images.trvl-media.com/lodging/34000000/33680000/33675900/33675891/ba4a685f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Impruneta [](https://www.expedia.ca/Impruneta-Hotels-La-Suite-Dei-Ricordi-Apartment-Between-Florence-And-Chianti.h33675891.Hotel-Information) 10/10 Exceptional (1 review) "Carina abitazione ristrutturata tipica del centro di un paesino toscano di campagna (Impruneta a pochi chilometri da Firenze). Ottimi impianti e sistemi che rendono l'abitazione molto comoda ed attrezzata (un televisore piatto per stanza, condizionatore presente, cucina attrezzata, ecc. Parcheggi a pochi passi e gratuiti dalla sera alla mattina con negozietti a pochi passi. Massima disponibilità dei proprietari e tipica gentilezza toscana." ![Italy](https://a.travel-assets.com/egds/marks/flags/it.svg) Anonymous traveller CA $161 CA $239 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Impruneta-Hotels-La-Suite-Dei-Ricordi-Apartment-Between-Florence-And-Chianti.h33675891.Hotel-Information) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117790000/117789600/117789522/e22a1f8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117790000/117789600/117789522/1c8dda56.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) ![Interior](https://images.trvl-media.com/lodging/118000000/117790000/117789600/117789522/1b1dee6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Montespertoli [](https://www.expedia.ca/Montespertoli-Hotels-Vrbo-Property.h117789522.Hotel-Information) CA $160 CA $194 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Montespertoli-Hotels-Vrbo-Property.h117789522.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/28000000/27470000/27461900/27461842/c7076070.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) ![Property grounds](https://images.trvl-media.com/lodging/28000000/27470000/27461900/27461842/72d49276.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) ### Vacation Home in Monteriggioni [](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) 10/10 Exceptional (12 reviews) "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 $362 CA $522 total includes taxes & fees Jan 23 - Jan 24 [](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) ![Smart TV](https://images.trvl-media.com/lodging/98000000/97110000/97106600/97106560/3f6b360d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/98000000/97110000/97106600/97106560/20fabb58.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) ![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) ### Vacation Home in Impruneta [](https://www.expedia.ca/Impruneta-Hotels-House-With-Separate-Entrance-At-The-Gates-Of-Florence-And-Chianti.h97106560.Hotel-Information) CA $116 CA $216 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Impruneta-Hotels-House-With-Separate-Entrance-At-The-Gates-Of-Florence-And-Chianti.h97106560.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/97000000/96140000/96134600/96134582/ebec6d19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96140000/96134600/96134582/d1d61167.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96140000/96134600/96134582/01f22c3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96140000/96134600/96134582/dcf0e569.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Montespertoli [](https://www.expedia.ca/Montespertoli-Hotels-Villa-Latini-Agriturismo-La-Capanna.h96134582.Hotel-Information) [](https://www.expedia.ca/Montespertoli-Hotels-Villa-Latini-Agriturismo-La-Capanna.h96134582.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) ![Fireplace](https://images.trvl-media.com/lodging/118000000/117300000/117295700/117295627/c8ec2ebf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117300000/117295700/117295627/0d2201aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117300000/117295700/117295627/ab10301d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Rignano sull'Arno [](https://www.expedia.ca/Rignano-SullArno-Hotels-Holiday-Home-Felciolina-With-Mountain-View.h117295627.Hotel-Information) CA $236 CA $240 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Rignano-SullArno-Hotels-Holiday-Home-Felciolina-With-Mountain-View.h117295627.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/48000000/47030000/47026200/47026113/f50de840.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/48000000/47030000/47026200/47026113/db15858a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/48000000/47030000/47026200/47026113/727fddb6.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 [](https://www.expedia.ca/Impruneta-Hotels-A-Luxury-Villa-ON-THE-Hills-OF-Florence.h47026113.Hotel-Information) CA $16,149 CA $17,460 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Impruneta-Hotels-A-Luxury-Villa-ON-THE-Hills-OF-Florence.h47026113.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/96000000/95540000/95538700/95538644/2c01476e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95540000/95538700/95538644/16a5d9ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95540000/95538700/95538644/cf327626.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/96000000/95540000/95538700/95538644/196c906a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Certaldo - Firenze [](https://www.expedia.ca/Certaldo-Hotels-Lendroit-Du-Coeur-En-Toscane.h95538644.Hotel-Information) CA $194 CA $352 total includes taxes & fees Jan 23 - Jan 24 [](https://www.expedia.ca/Certaldo-Hotels-Lendroit-Du-Coeur-En-Toscane.h95538644.Hotel-Information) ![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117880000/117875500/117875443/2fad9f1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117880000/117875500/117875443/3b9259d6.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/ef70c10d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/118000000/117880000/117875500/117875443/7ce71ecc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Montevarchi [](https://www.expedia.ca/Montevarchi-Hotels-Between-Florence.h117875443.Hotel-Information) CA $184 CA $237 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Montevarchi-Hotels-Between-Florence.h117875443.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/84000000/83360000/83354900/83354864/f910598d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/84000000/83360000/83354900/83354864/b68fa7ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83360000/83354900/83354864/04a72517.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/84000000/83360000/83354900/83354864/1858bc78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Gaiole in Chianti [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Casa-Vacanze-Chianti-Summer-With-Pool.h83354864.Hotel-Information) CA $744 CA $889 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Casa-Vacanze-Chianti-Summer-With-Pool.h83354864.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) ![Property grounds](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165667/69c1b25d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165667/50bbe6a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165667/303f6717.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Montespertoli [](https://www.expedia.ca/Montespertoli-Hotels-Villa-Il-Frantoio-With-Shared-Pool.h78165667.Hotel-Information) CA $247 CA $250 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Montespertoli-Hotels-Villa-Il-Frantoio-With-Shared-Pool.h78165667.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/79000000/78590000/78589900/78589849/a98222c0.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) ![Pool](https://images.trvl-media.com/lodging/79000000/78590000/78589900/78589849/7056308f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/79000000/78590000/78589900/78589849/c00bb41f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in BARBERINO TAVARNELLE [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Apartment-Vernaccia-Country-House-Agriturismo-With-Pool.h78589849.Hotel-Information) 10/10 Exceptional (1 review) "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 $366 CA $470 total includes taxes & fees Jan 23 - Jan 24 [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Apartment-Vernaccia-Country-House-Agriturismo-With-Pool.h78589849.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) ![Interior](https://images.trvl-media.com/lodging/36000000/35780000/35773400/35773392/2fc87746.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/36000000/35780000/35773400/35773392/b7437f71.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) ### Vacation Home in MONTERIGGIONI [](https://www.expedia.ca/Monteriggioni-Hotels-Apart-Charm.h35773392.Hotel-Information) 10/10 Exceptional (1 review) "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 $434 CA $688 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Monteriggioni-Hotels-Apart-Charm.h35773392.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/103000000/102120000/102118900/102118899/7c89b7dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/103000000/102120000/102118900/102118899/7cb9dd4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/103000000/102120000/102118900/102118899/25eeffa0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102120000/102118900/102118899/451edd82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Castelnuovo Berardenga [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-Vacation-Home-Limonaia-With-Shared-Pool.h102118899.Hotel-Information) 10/10 Exceptional (1 review) "Pros: The view and unique traditional apartment. Cons: -" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $650 CA $791 total includes taxes & fees Jan 23 - Jan 24 [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-Vacation-Home-Limonaia-With-Shared-Pool.h102118899.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/124000000/123170000/123161400/123161359/928c511a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/124000000/123170000/123161400/123161359/3480436d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/124000000/123170000/123161400/123161359/11b7eb29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/124000000/123170000/123161400/123161359/6dcca57d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Montevarchi [](https://www.expedia.ca/Montevarchi-Hotels-Holiday-Home-Poggio-Loccano-With-Private-Garden-And-Balcony.h123161359.Hotel-Information) CA $567 CA $728 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Montevarchi-Hotels-Holiday-Home-Poggio-Loccano-With-Private-Garden-And-Balcony.h123161359.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/91000000/90940000/90939400/90939308/30f8a5ab.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/91000000/90940000/90939400/90939308/5378f707.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90940000/90939400/90939308/f777443c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90940000/90939400/90939308/7e9fd72b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Castelfranco di Sopra [](https://www.expedia.ca/Castelfranco-Piandisco-Hotels-Holiday-Home-Le-Balze-With-Mountain-View.h90939308.Hotel-Information) CA $473 CA $571 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Castelfranco-Piandisco-Hotels-Holiday-Home-Le-Balze-With-Mountain-View.h90939308.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/33000000/32650000/32642500/32642446/c66ff569.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/33000000/32650000/32642500/32642446/1ce4c9f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32650000/32642500/32642446/99362b4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, video library](https://images.trvl-media.com/lodging/33000000/32650000/32642500/32642446/c94f26f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in San Donato [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Dolce-Cuore-Luxe-Apartment-IN-Heart-OF-Tuscany.h32642446.Hotel-Information) CA $128 CA $367 total includes taxes & fees Jan 23 - Jan 24 [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Dolce-Cuore-Luxe-Apartment-IN-Heart-OF-Tuscany.h32642446.Hotel-Information) ![4 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/106000000/105470000/105466300/105466234/b2e0f021.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/106000000/105470000/105466300/105466234/2e4d7af9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105470000/105466300/105466234/097e241e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/106000000/105470000/105466300/105466234/67785df1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Rignano sull'Arno [](https://www.expedia.ca/Rignano-SullArno-Hotels-Holiday-Home-Villa-Silvia-With-Private-Pool.h105466234.Hotel-Information) CA $3,261 CA $4,332 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Rignano-SullArno-Hotels-Holiday-Home-Villa-Silvia-With-Private-Pool.h105466234.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=2026-02-04&endDate=2026-02-05®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=2026-04-21&d1=2026-04-21&endDate=2026-04-24&d2=2026-04-24&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=2026-04-21&d1=2026-04-21&endDate=2026-04-24&d2=2026-04-24&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=2026-04-21&d1=2026-04-21&endDate=2026-04-24&d2=2026-04-24&lodging=APART_HOTEL) Residences [](https://www.expedia.ca/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy®ionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-04-21&d1=2026-04-21&endDate=2026-04-24&d2=2026-04-24&lodging=RESIDENCE) 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=2026-04-21&d1=2026-04-21&endDate=2026-04-24&d2=2026-04-24&lodging=VACATION_HOME) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy®ionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-04-21&d1=2026-04-21&endDate=2026-04-24&d2=2026-04-24&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=2026-04-21&d1=2026-04-21&endDate=2026-04-24&d2=2026-04-24&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=2026-04-21&d1=2026-04-21&endDate=2026-04-24&d2=2026-04-24&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=2026-04-21&d1=2026-04-21&endDate=2026-04-24&d2=2026-04-24&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-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 ![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 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) ![Castello Vicchiomaggio](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/3167b59e_y.jpg) ### Castello Vicchiomaggio 10/10 Excellent "This beautiful property stole our hearts back in 2019, when my now-wife first visited this magical place. Six years later, we returned — this time to celebrate our wedding reception after tying the knot a few months earlier. From start to finish, everything was beyond wonderful. A special mention to Sandra, the amazing coordinator who made everything run so smoothly, and her fantastic team — Delfina and the lovely lady (whose name, unfortunately, I’ve forgotten) who graciously welcomed and ushered our guests upon arrival. Every detail was handled with care and professionalism. The food and Chianti wines during our celebration were absolutely exceptional — truly a highlight that everyone still talks about! The breakfast and dinner staff were attentive, kind, and ensured everything was perfect throughout our stay. Our rooms were clean, comfortable, and beautifully maintained, with housekeeping doing a fantastic job. We also had the privilege of meeting Mr. John Matta, the owner — such a gracious and inspiring man who leads an extraordinary team. All of our guests loved their stay, and we left with hearts full of joy and gratitude. We can’t wait to come back again — hopefully for our anniversary next time." [](https://expedia.ca/Greve-In-Chianti-Hotels-Castello-Vicchiomaggio.h7564854.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 Vacation Homes information | Number of reviews | 1 | | ----------------- | ------------------ | | Accommodation | 436 Vacation Homes | | Lowest Price | CA $183 | | Highest Price | CA $17,460 | ## 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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