Title: Chianti Region Vacation Home Rentals from CA $109: 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) ![](https://images.trvl-media.com/place/603148/a6b4be95-df3f-44a2-bf6d-bb1e6f500def.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 [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 two months [May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 26 - Jun 28](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-06-26&endDate=2026-06-28&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 entrance](https://images.trvl-media.com/lodging/43000000/42410000/42405100/42405029/343d0b2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Duplex, 2 Bedrooms (Mimosa) | Living area](https://images.trvl-media.com/lodging/43000000/42410000/42405100/42405029/0b31f6fb.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 CA $183 CA $208 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Agriturismo-La-Ferrozzola.h42405029.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/84000000/83590000/83580400/83580374/77d8ad70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83590000/83580400/83580374/15eff195.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83590000/83580400/83580374/f52ea845.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) ### Vacation Home in Barberino Tavarnelle [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Vrbo-Property.h83580374.Hotel-Information) 9.8/10 Exceptional (9 reviews) "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 $237 CA $333 total includes taxes & fees Mar 4 - Mar 5 [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Vrbo-Property.h83580374.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/19000000/18980000/18975400/18975333/075690f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18980000/18975400/18975333/85723b13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/19000000/18980000/18975400/18975333/0ecb2ff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/19000000/18980000/18975400/18975333/e12d84b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Castiglion fibocchi [](https://www.expedia.ca/Castiglion-Fibocchi-Hotels-Casa-Da-Vinci-For-Two.h18975333.Hotel-Information) 8.0/10 Very good (1 review) "Sauber gemütlich, nette Atmosphäre Einrichtung ist ausreichend." ![Germany](https://a.travel-assets.com/egds/marks/flags/de.svg) Perdita I. CA $64 CA $109 total includes taxes & fees Mar 4 - Mar 5 [](https://www.expedia.ca/Castiglion-Fibocchi-Hotels-Casa-Da-Vinci-For-Two.h18975333.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/126000000/125320000/125312900/125312869/579ecb81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/126000000/125320000/125312900/125312869/d4153827.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/126000000/125320000/125312900/125312869/0bda44dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/126000000/125320000/125312900/125312869/1275c1ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in San Vincenzo A Torri [](https://www.expedia.ca/Scandicci-Hotels-Cozy-Holiday-Home-With-Garden-In-Tuscany-San-Vincenzo-A-Torri.h125312869.Hotel-Information) CA $272 CA $360 total includes taxes & fees Mar 25 - Mar 26 [](https://www.expedia.ca/Scandicci-Hotels-Cozy-Holiday-Home-With-Garden-In-Tuscany-San-Vincenzo-A-Torri.h125312869.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) ![Pool](https://images.trvl-media.com/lodging/84000000/83360000/83354900/83354864/a7d5ba95.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 $737 CA $880 total includes taxes & fees Mar 5 - Mar 6 [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Casa-Vacanze-Chianti-Summer-With-Pool.h83354864.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/88000000/87710000/87701400/87701337/d3075204.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/88000000/87710000/87701400/87701337/f9c1b398.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, highchair, cookware/dishes/utensils](https://images.trvl-media.com/lodging/88000000/87710000/87701400/87701337/5576c246.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi](https://images.trvl-media.com/lodging/88000000/87710000/87701400/87701337/970b896e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Greve in Chianti [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Vacation-Home-Fattoria-LOttavo-In-Greve-In-Chianti-2-Persons.h87701337.Hotel-Information) CA $200 CA $206 total includes taxes & fees Mar 6 - Mar 7 [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Vacation-Home-Fattoria-LOttavo-In-Greve-In-Chianti-2-Persons.h87701337.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) ![TV](https://images.trvl-media.com/lodging/124000000/123170000/123161400/123161359/11b7eb29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/124000000/123170000/123161400/123161359/83ca9227.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) ### Vacation Home in Montevarchi [](https://www.expedia.ca/Montevarchi-Hotels-Holiday-Home-Poggio-Loccano-With-Private-Garden-And-Balcony.h123161359.Hotel-Information) CA $311 CA $471 total includes taxes & fees Mar 4 - Mar 5 [](https://www.expedia.ca/Montevarchi-Hotels-Holiday-Home-Poggio-Loccano-With-Private-Garden-And-Balcony.h123161359.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) ![Interior](https://images.trvl-media.com/lodging/20000000/19150000/19149100/19149003/cb3775a2.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) ![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) ### Vacation Home in impruneta [](https://www.expedia.ca/Impruneta-Hotels-House-With-Views-Of-The-Chianti.h19149003.Hotel-Information) 10/10 Exceptional (2 reviews) "Great place, quaint and spacious. Beautiful view and equipped with everything needed for a pleasant stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Becky H. CA $128 CA $389 total includes taxes & fees Mar 25 - Mar 26 [](https://www.expedia.ca/Impruneta-Hotels-House-With-Views-Of-The-Chianti.h19149003.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) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/28000000/27470000/27461900/27461842/1d63c974.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 $358 CA $517 total includes taxes & fees Mar 4 - Mar 5 [](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 dining](https://images.trvl-media.com/lodging/70000000/69540000/69539700/69539666/df9cff0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/70000000/69540000/69539700/69539666/e894f062.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/70000000/69540000/69539700/69539666/17e0627e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/70000000/69540000/69539700/69539666/3f6956a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Greve in Chianti [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Casagreve-Stylish-House-In-Tuscan-Village-Breathtaking-View-From-Its-Terrace.h69539666.Hotel-Information) 10/10 Exceptional (9 reviews) "This was my favorite stay during our travels throughout Italy. Restaurants on the square or dining out on the lovely balcony. We had a wonderful stay here. Perfect location for dayctrips to Sienna and Florence, bike riding through Tuscany, . Great hosts as well!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda L. CA $512 CA $582 total includes taxes & fees Mar 10 - Mar 11 [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Casagreve-Stylish-House-In-Tuscan-Village-Breathtaking-View-From-Its-Terrace.h69539666.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/40000000/39990000/39983400/39983368/6e6f272f.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) ### Vacation Home in impruneta [](https://www.expedia.ca/Impruneta-Hotels-Beautiful-Tuscan-Farmhouse-With-Large-Spaces-And-Panoramic-Views.h39983368.Hotel-Information) 9.6/10 Exceptional (25 reviews) "Loved the property and views,the owner was very helpful and informative would definitely come back" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andy P. CA $133 CA $413 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Impruneta-Hotels-Beautiful-Tuscan-Farmhouse-With-Large-Spaces-And-Panoramic-Views.h39983368.Hotel-Information) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/107000000/106010000/106004000/106003929/2a16bc08.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) ![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/107000000/106010000/106004000/106003929/54f20ef9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Certaldo [](https://www.expedia.ca/Certaldo-Hotels-Holiday-Home-Sandra-House-With-Private-Garden-And-Wi-Fi.h106003929.Hotel-Information) 10/10 Exceptional (1 review) "Pros: Die familiäre Aufnahme und Unterstützung war sehr angenehm." ![Germany](https://a.travel-assets.com/egds/marks/flags/de.svg) Anonymous traveller CA $124 CA $207 total includes taxes & fees Mar 4 - Mar 5 [](https://www.expedia.ca/Certaldo-Hotels-Holiday-Home-Sandra-House-With-Private-Garden-And-Wi-Fi.h106003929.Hotel-Information) ![1 bedroom, desk, iron/ironing board, WiFi](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) ![Flat-screen TV, books](https://images.trvl-media.com/lodging/34000000/33680000/33675900/33675891/1a6006b6.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 $160 CA $237 total includes taxes & fees Mar 4 - Mar 5 [](https://www.expedia.ca/Impruneta-Hotels-La-Suite-Dei-Ricordi-Apartment-Between-Florence-And-Chianti.h33675891.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) ![Dining](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165667/50bbe6a6.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) ![Outdoor dining](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165667/e287c79c.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 $245 CA $249 total includes taxes & fees Mar 14 - Mar 15 [](https://www.expedia.ca/Montespertoli-Hotels-Villa-Il-Frantoio-With-Shared-Pool.h78165667.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/124000000/123850000/123843300/123843285/cfd96991.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/124000000/123850000/123843300/123843285/ad3649ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/124000000/123850000/123843300/123843285/bed92807.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/124000000/123850000/123843300/123843285/2e5fef1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Poggibonsi [](https://www.expedia.ca/Poggibonsi-Hotels-Charming-Villa-In-Tuscan-Vineyard-Estate-With-Pool-BBQ.h123843285.Hotel-Information) CA $195 CA $452 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Poggibonsi-Hotels-Charming-Villa-In-Tuscan-Vineyard-Estate-With-Pool-BBQ.h123843285.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) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96140000/96134600/96134582/28da50bb.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) ![Interior](https://images.trvl-media.com/lodging/96000000/95540000/95538700/95538644/2c01476e.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) ![Interior](https://images.trvl-media.com/lodging/96000000/95540000/95538700/95538644/cf327626.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) ### Vacation Home in Certaldo - Firenze [](https://www.expedia.ca/Certaldo-Hotels-Lendroit-Du-Coeur-En-Toscane.h95538644.Hotel-Information) CA $192 CA $349 total includes taxes & fees Mar 6 - Mar 7 [](https://www.expedia.ca/Certaldo-Hotels-Lendroit-Du-Coeur-En-Toscane.h95538644.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) ![Exterior](https://images.trvl-media.com/lodging/118000000/117300000/117295700/117295627/ab10301d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/118000000/117300000/117295700/117295627/821001fb.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) ### Vacation Home in Rignano sull'Arno [](https://www.expedia.ca/Rignano-SullArno-Hotels-Holiday-Home-Felciolina-With-Mountain-View.h117295627.Hotel-Information) CA $238 CA $241 total includes taxes & fees Mar 5 - Mar 6 [](https://www.expedia.ca/Rignano-SullArno-Hotels-Holiday-Home-Felciolina-With-Mountain-View.h117295627.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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/103000000/102120000/102118900/102118899/7cb9dd4c.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 $374 CA $477 total includes taxes & fees Mar 4 - Mar 5 [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-Vacation-Home-Limonaia-With-Shared-Pool.h102118899.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) ![Interior](https://images.trvl-media.com/lodging/118000000/117880000/117875500/117875443/70e917ee.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) ![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) ### Vacation Home in Montevarchi [](https://www.expedia.ca/Montevarchi-Hotels-Between-Florence.h117875443.Hotel-Information) CA $182 CA $235 total includes taxes & fees Mar 4 - Mar 5 [](https://www.expedia.ca/Montevarchi-Hotels-Between-Florence.h117875443.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=2026-03-17&endDate=2026-03-18®ionId=603148&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AA_SPRING_PROMO_603148) ## 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=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&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=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=APARTMENT) Residences [](https://www.expedia.ca/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy®ionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&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=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&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=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=COTTAGE) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy®ionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=APART_HOTEL) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy®ionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=CHALET) Condos [](https://www.expedia.ca/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy®ionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&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=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=CABIN) ![](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 ![Salvadonica - Borgo del Chianti](https://images.trvl-media.com/lodging/21000000/20490000/20484000/20483959/56ce48bb_y.jpg) ### Salvadonica - Borgo del Chianti 10/10 Excellent "The staff were very helpful and the buffet breakfast was delicious! " [](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 "Very good place, clean, good service, great food, the rooms were amazing." [](https://expedia.ca/Colle-Di-Val-DElsa-Hotels-Hotel-Palazzo-San-Lorenzo-SPA.h3474921.Hotel-Information) ![hu Firenze Certosa camping in town](https://images.trvl-media.com/lodging/102000000/101510000/101503700/101503652/f6cba490_y.jpg) ### hu Firenze Certosa camping in town 10/10 Excellent "Fantastic! The staff was very helpfull, the rooms were impeacable (and warm) and the dinner at the restaurant was delicious. Better than an hotel in our opinion. Congrats! The only drawback as lack of EV charger... but they said it was coming.." [](https://expedia.ca/Impruneta-Hotels-Firenze-Certosa-Camping.h101503652.Hotel-Information) ![Villa Le Barone](https://images.trvl-media.com/lodging/3000000/2550000/2542300/2542211/2748a205_y.jpg) ### Villa Le Barone 10/10 Excellent "Great experience!!!" [](https://expedia.ca/Greve-In-Chianti-Hotels-Villa-Le-Barone.h2542211.Hotel-Information) ![Villa Casagrande Resort & SPA](https://images.trvl-media.com/lodging/1000000/900000/891700/891661/994bfd62_y.jpg) ### Villa Casagrande Resort & SPA 8/10 Good "Beautiful property." [](https://expedia.ca/Figline-E-Incisa-Valdarno-Hotels-Villa-Casagrande-Resort-SPA.h891661.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) ![Borgo Del Cabreo](https://images.trvl-media.com/lodging/18000000/17970000/17963800/17963776/6c72b535_y.jpg) ### Borgo Del Cabreo 10/10 Excellent "This was our second stay here. The service is excellent, staff are so friendly and the room was spotless with a stunning view at breakfast sitting outside. Nice little spread for breakfast. " [](https://expedia.ca/Greve-In-Chianti-Hotels-Borgo-Del-Cabreo.h17963776.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) ![Castello Vicchiomaggio](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/62d09fdf_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) ## Find out more about Chianti Region ## Chianti Region Vacation Homes information | Number of reviews | 61 | | ----------------- | ------------------ | | Accommodation | 436 Vacation Homes | | Lowest Price | CA $109 | | Highest Price | CA $880 | ## 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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