Title: Chianti Region Vacation Home Rentals : 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://a.travel-assets.com/findyours-php/viewfinder/images/res70/157000/157505-Chianti-Region.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Chianti Region Vacation Rentals ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=VACATION_HOME&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) ![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) ![Exterior](https://images.trvl-media.com/lodging/43000000/42410000/42405100/42405029/313690ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Agriturismo La Ferrozzola Castellina in Chianti 9.4/10 Exceptional (9) "Very nice agriturismo. " CA $186 CA $211 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Agriturismo-La-Ferrozzola.h42405029.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/22000000/21120000/21114900/21114825/679da5ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/22000000/21120000/21114900/21114825/dd9f1e7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/22000000/21120000/21114900/21114825/18de298e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/22000000/21120000/21114900/21114825/d9870570.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Borgo Argiano Castelnuovo Berardenga 10/10 Exceptional (70) "Very comfortable stay. " CA $405 CA $459 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-Borgo-Argiano.h21114825.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) ![Outdoor dining](https://images.trvl-media.com/lodging/48000000/47030000/47026200/47026113/d9e20b86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A LUXURY VILLA ON THE HILLS OF FLORENCE Impruneta CA $16,228 CA $18,113 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Impruneta-Hotels-A-Luxury-Villa-ON-THE-Hills-OF-Florence.h47026113.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/20000000/19150000/19149100/19149003/4440a68e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/20000000/19150000/19149100/19149003/ff740e0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/20000000/19150000/19149100/19149003/405b4867.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/20000000/19150000/19149100/19149003/83ddb8ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### House with views of the Chianti impruneta 10/10 Exceptional (1) "Great place, quaint and spacious. Beautiful view and equipped with everything needed for a pleasant stay. " CA $110 CA $375 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Impruneta-Hotels-House-With-Views-Of-The-Chianti.h19149003.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) ![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/e1a1ee18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/113000000/112480000/112477800/112477726/05c4a567.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home 'Piccolo Angolo Di Tranquillità' with Private Garden and Wi-Fi Poggibonsi 10/10 Exceptional (2) "Pros: Tutto stupendo la casa la posizione è. La dolcezza della proprietaria" CA $146 CA $202 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Poggibonsi-Hotels-Holiday-Home-Piccolo-Angolo-Di-Tranquillita-With-Private-Garden-And-Wi-Fi.h112477726.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) ![Interior](https://images.trvl-media.com/lodging/79000000/78590000/78589900/78589849/004a5c84.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) ![Outdoor dining](https://images.trvl-media.com/lodging/79000000/78590000/78589900/78589849/a6521e68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment 'Vernaccia Country House - Agriturismo' with Pool, Garden & Wi-Fi BARBERINO TAVARNELLE 10/10 Exceptional (1) "Das Objekt liegt zwischen Florenz und Siena umgeben von Olivenbäumen. Die Lage ist perfekt für Ausflüge." CA $405 CA $509 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Apartment-Vernaccia-Country-House-Agriturismo-With-Pool.h78589849.Hotel-Information) ![2 bedrooms, internet, bed sheets](https://images.trvl-media.com/lodging/40000000/39990000/39983400/39983368/34638ab1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39990000/39983400/39983368/6671f978.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/40000000/39990000/39983400/39983368/w2034h1365x14y0-0edee40d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/40000000/39990000/39983400/39983368/acc5b1eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wonderful Tuscan farmhouse with large spaces and panoramic views impruneta 9.8/10 Exceptional (23) "If you are looking for a beautiful area close to but not in Florence this is the place for you! Rustic Tuscan farmhouse that is just lovely with beautiful views. Mattia is a wonderful host with great recommendations for visits and food. This is close to all that Tuscany has to offer, would definitely stay here again ." CA $122 CA $393 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Impruneta-Hotels-Beautiful-Tuscan-Farmhouse-With-Large-Spaces-And-Panoramic-Views.h39983368.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/84000000/83590000/83580400/83580374/2c97b1ed.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) ![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) ### Chianti Craft House Badia a Passignano Barberino Tavarnelle 9.8/10 Exceptional (8) "Great food in the area. Beautiful church tour and a fantastic host for our stay!" CA $212 CA $309 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Vrbo-Property.h83580374.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) ![Exterior](https://images.trvl-media.com/lodging/103000000/102120000/102118900/102118895/1bf394da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/103000000/102120000/102118900/102118895/025d6df5.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) ### Vacation Home "Casalino" with Shared Pool, Shared Garden & Wi-Fi Castelnuovo Berardenga CA $606 CA $787 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-Vacation-Home-Casalino-With-Shared-Pool.h102118895.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/117000000/116500000/116495300/116495207/b12869c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116500000/116495300/116495207/fe7fc54f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116500000/116495300/116495207/b428bb2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/117000000/116500000/116495300/116495207/5d13d3ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### THE CASTELLETTO Toscana CA $211 CA $276 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-Vrbo-Property.h116495207.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) ![Exterior detail](https://images.trvl-media.com/lodging/107000000/106010000/106004000/106003929/71637324.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) ### Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi Certaldo 10/10 Exceptional (1) "Pros: Die familiäre Aufnahme und Unterstützung war sehr angenehm." CA $192 CA $276 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Certaldo-Hotels-Holiday-Home-Sandra-House-With-Private-Garden-And-Wi-Fi.h106003929.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) ![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) ![Outdoor dining](https://images.trvl-media.com/lodging/97000000/96690000/96687900/96687854/6d8f1a28.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) ### Pet-friendly Holiday Home 'Poggio Al Mandorlo' with Garden, Whirlpool & Wi-Fi 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." CA $249 CA $325 total includes taxes & fees Oct 21 - Oct 22 [](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) ![Pool](https://images.trvl-media.com/lodging/28000000/27470000/27461900/27461842/bea6b45a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/28000000/27470000/27461900/27461842/c7076070.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) ### 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. 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... CA $393 CA $555 total includes taxes & fees Oct 12 - Oct 13 [](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) ![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) ![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) ![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) ### Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi Montespertoli CA $357 CA $360 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Montespertoli-Hotels-Villa-Il-Frantoio-With-Shared-Pool.h78165667.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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117880000/117875500/117875443/3b9259d6.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) ### Between Florence, Siena and Chianti Montevarchi CA $195 CA $252 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Montevarchi-Hotels-Between-Florence.h117875443.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) ![Interior](https://images.trvl-media.com/lodging/118000000/117300000/117295700/117295627/5196db78.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) ### Holiday Home 'Felciolina' with Mountain View, Private Terrace and Wi-Fi Rignano sull'Arno CA $237 CA $241 total includes taxes & fees Nov 3 - Nov 4 [](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) ![Property grounds](https://images.trvl-media.com/lodging/96000000/95540000/95538700/95538644/196c906a.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) ![Dining](https://images.trvl-media.com/lodging/96000000/95540000/95538700/95538644/b1e3c029.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Your nest in the Tuscany countryside Certaldo - Firenze CA $179 CA $339 total includes taxes & fees Oct 18 - Oct 19 [](https://www.expedia.ca/Certaldo-Hotels-Lendroit-Du-Coeur-En-Toscane.h95538644.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) ![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) ![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) ### Tuscan House Relax in the heart of the Tuscan countryside Montespertoli CA $146 CA $180 total includes taxes & fees Oct 10 - Oct 11 [](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) ![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) ### APART. OF CHARM, AIR CONDITIONING, FENCED POOL IN THE HEART OF CHIANTI-FLORENCE 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. " CA $437 CA $686 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Monteriggioni-Hotels-Apart-Charm.h35773392.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/106000000/105470000/105466300/105466234/9b1122b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105470000/105466300/105466234/0cee9b19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/106000000/105470000/105466300/105466234/609d2d59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home 'Villa Silvia' with Private Pool, Wi-Fi and Air Conditioning Rignano sull'Arno CA $2,499 CA $3,578 total includes taxes & fees Oct 10 - Oct 11 [](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=2025-10-23&endDate=2025-10-24®ionId=603148&adults=2&lodging=VACATION_HOME&sort=RECOMMENDED&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%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 ![Relais Vignale & Spa](//images.trvl-media.com/lodging/2000000/1130000/1122100/1122097/72f1acd5_y.jpg) ### Relais Vignale & Spa 10/10 Excellent "Beautiful property, friendly staff, nice breakfast buffet all made this place a great experience. We had multiple dining options within walking distance and cute shopping. The views are so good, they look fake." [](https://expedia.ca/Radda-In-Chianti-Hotels-Relais-Vignale-Spa.h1122097.Hotel-Information) ![Il Borro - Relais & Châteaux](//images.trvl-media.com/lodging/6000000/5590000/5585700/5585638/4a6bd899_y.jpg) ### Il Borro - Relais & Châteaux 10/10 Excellent "Charming property. Excellent staff and food options. Would recommend booking activities early and try a little of everything. Would also recommend trying each of the three restaurants and a variety of their wines. " [](https://expedia.ca/Loro-Ciuffenna-Hotels-Il-Borro-Relais-Chateaux.h5585638.Hotel-Information) ![Villa I Barronci Resort & Spa](//images.trvl-media.com/lodging/3000000/2530000/2523800/2523750/d7de1ccd_y.jpg) ### Villa I Barronci Resort & Spa 10/10 Excellent "This magnificent Hotel exceeded all our expectations. The rooms were very generous is size and the beds were so comfy. Breakfast was exceptional too.... The heated swimming pool with Jacuzzi and the view of the countryside was breathtaking." [](https://expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Villa-I-Barronci-Resort-Spa.h2523750.Hotel-Information) ![Palazzo Leopoldo Dimora Storica & Spa](//images.trvl-media.com/lodging/1000000/920000/911700/911656/95292913_y.jpg) ### Palazzo Leopoldo Dimora Storica & Spa 10/10 Excellent "Excellent breakfast. " [](https://expedia.ca/Radda-In-Chianti-Hotels-Palazzo-Leopoldo-Dimora-Storica-Spa.h911656.Hotel-Information) ![Salvadonica - Borgo del Chianti](//images.trvl-media.com/lodging/21000000/20490000/20484000/20483959/56ce48bb_y.jpg) ### Salvadonica - Borgo del Chianti 10/10 Excellent "Very friendly staff. Stunning views! Excellent restaurant on site with breakfast included. Great rooms with plenty of old-world charm. Can't wait to come back!" [](https://expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Salvadonica.h20483959.Hotel-Information) ![Castello di Spaltenna- Small Luxury Hotels of the World](//images.trvl-media.com/lodging/3000000/2550000/2540800/2540741/75ac6194_y.jpg) ### Castello di Spaltenna- Small Luxury Hotels of the World 10/10 Excellent "This hotel is wonderful with beautiful views from the terrace! The only complaint is the number of stairs you have to take if staying on upper floors (no elevator) - my husband has a bad back so that’s a consideration. Also, wish they would accommodate all the guests in the gourmet restaurant as we couldn’t get a reservation during our 2-day stay! Book ahead of time!" [](https://expedia.ca/Gaiole-In-Chianti-Hotels-Castello-Di-Spaltenna.h2540741.Hotel-Information) ![Castello di Fonterutoli Wine Resort](//images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/9f05cf5a_y.jpg) ### Castello di Fonterutoli Wine Resort 10/10 Excellent "Amazing experience all around! Stayed for 2 nights!" [](https://expedia.ca/Castellina-In-Chianti-Hotels-Castello-Di-Fonterutoli.h5172395.Hotel-Information) ![Hu Norcenni Girasole Village](//images.trvl-media.com/lodging/4000000/3540000/3530100/3530075/dcea3a98_y.jpg) ### Hu Norcenni Girasole Village 10/10 Excellent "Good value for money" [](https://expedia.ca/Figline-E-Incisa-Valdarno-Hotels-Norcenni-Girasole-Village.h3530075.Hotel-Information) ![Borgo Vescine](//images.trvl-media.com/lodging/2000000/1190000/1180600/1180553/8d2f3252_y.jpg) ### Borgo Vescine 10/10 Excellent "This was a beautiful location. The room was spacious and loved the patio for coffee in the mornings. It was very private. We enjoyed the pool and restaurants were great. Breakfast was amazing. We did the picnic and dinner in the Olive Garden and loved getting to know others at our table. The chefs food choices were so wonderful. We would definitely stay again. " [](https://expedia.ca/Radda-In-Chianti-Hotels-Il-Borgo-Di-Vescine.h1180553.Hotel-Information) ## Find out more about Chianti Region ## Chianti Region Vacation Homes information | Number of reviews | | | --- | --- | | Accommodation | Vacation Homes | | Lowest Price | | | Highest Price | | ## 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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[Flights from Gaiole in Chianti](https://www.expedia.ca/lp/flights/603149/flights-from-gaiole-in-chianti) - [Buondonno Winery](https://www.expedia.ca/Buondonno-Winery-Castellina-in-Chianti.d553248635823420151.Vacation-Attraction) - [Casa Vinicola Luigi Cecchi](https://www.expedia.ca/Casa-Vinicola-Luigi-Cecchi-Castellina-in-Chianti.d6103262.Vacation-Attraction) - [Visit Castelnuovo dei Sabbioni](https://www.expedia.ca/Castelnuovo-Dei-Sabbioni.dx602580) - [Church of San Sigismondo](https://www.expedia.ca/Church-Of-San-Sigismondo-Gaiole-in-Chianti.d6238140.Vacation-Attraction) - [Visit Gaiole in Chianti](https://www.expedia.ca/Gaiole-In-Chianti.dx603149) - [Visit Greve in Chianti](https://www.expedia.ca/Greve-In-Chianti.dx601773) - [Visit Meleto](https://www.expedia.ca/Meleto.dx6292517) - [Visit Montefioralle](https://www.expedia.ca/Montefioralle.dx3000404943) - [Visit Panzano in Chianti](https://www.expedia.ca/Panzano-In-Chianti.dx602564) - [Visit Ponte Agli Stolli](https://www.expedia.ca/Ponte-Agli-Stolli.dx6342228) - [Visit Radda in Chianti](https://www.expedia.ca/Radda-In-Chianti.dx601693) - [Visit San Donato in Poggio](https://www.expedia.ca/San-Donato-In-Poggio.dx6292835) - [Visit Sicelle](https://www.expedia.ca/Sicelle.dx6343024) - [Visit Vertine](https://www.expedia.ca/Vertine.dx632712480144572416) - [Car rental Castellina in Chianti](https://www.expedia.ca/Car-Rentals-In-Castellina-In-Chianti.d55534.Car-Rental-Guide) - [Car rental Greve in Chianti](https://www.expedia.ca/Car-Rentals-In-Greve-In-Chianti.d601773.Car-Rental-Guide) - [Car rental Panzano in Chianti](https://www.expedia.ca/Car-Rentals-In-Panzano-In-Chianti.d602564.Car-Rental-Guide) - [Car rental Radda in Chianti](https://www.expedia.ca/Car-Rentals-In-Radda-In-Chianti.d601693.Car-Rental-Guide) - [Things to do in Fonterutoli](https://www.expedia.ca/Things-To-Do-In-Fonterutoli.d6342141.Travel-Guide-Activities) - [Things to do in Gaiole in Chianti](https://www.expedia.ca/Things-To-Do-In-Gaiole-In-Chianti.d603149.Travel-Guide-Activities) - [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)