Title: Chianti Region Vacation Rentals from CA $158: Short-Term Rentals for 2026 | 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)[Flights to Chianti Region](https://expedia.ca/Cheap-Flights-To-Chianti-Region.d603148.Travel-Guide-Flights)[Things to do in Chianti Region](https://expedia.ca/Things-To-Do-In-Chianti-Region.d603148.Travel-Guide-Activities)[Chianti Region Car Rentals](https://expedia.ca/Car-Rentals-In-Chianti-Region.d603148.Car-Rental-Guide)[Chianti Region Vacation Packages](https://expedia.ca/Chianti-Region.d603148.Destination-Travel-Guides) ![Chianti Region showing farmland](https://images.trvl-media.com/place/603148/a6b4be95-df3f-44a2-bf6d-bb1e6f500def.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Chianti Region Vacation Rentals - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-05-08&endDate=2026-05-10&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 rentals ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/40000000/39680000/39673400/39673326/3db308c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Apartment, 1 Bedroom, Non Smoking, Kitchen | Living area](https://images.trvl-media.com/lodging/40000000/39680000/39673400/39673326/bdde45d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/40000000/39680000/39673400/39673326/45947cc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, oven, stovetop, espresso maker](https://images.trvl-media.com/lodging/40000000/39680000/39673400/39673326/45f2e5f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rocca Palazzaccio [](https://www.expedia.ca/Impruneta-Hotels-Rocca-Palazzaccio.h39673326.Hotel-Information) Impruneta 9.0/10 Wonderful (14 reviews) "A lovely stay at this property with our 2 year old.The apartment had everything we needed and communication with the host was very good There are steep hills to access the property by car or foot so bear that in mind but we managed fine with a pram and a car its just worth noting Handy to have laundry facilities on site aswell. There is a coop just a few minutes down the road Lovely views and a clean pool which was perfect for our little one to use and toys there that he could play in the... ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Lauren CA $125 CA $342 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Impruneta-Hotels-Rocca-Palazzaccio.h39673326.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1140000/1131000/1130942/b50d05a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1140000/1131000/1130942/7a95d976.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 9:00 AM to 7:00 PM, sun loungers](https://images.trvl-media.com/lodging/2000000/1140000/1131000/1130942/6055a736.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/2000000/1140000/1131000/1130942/0dc1dfcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Cassia di Baccano [](https://www.expedia.ca/Loro-Ciuffenna-Hotels-Villa-Cassia-Di-Baccano.h1130942.Hotel-Information) Loro Ciuffenna 9.4/10 Exceptional (23 reviews) "The staff were great and the villa was amazing" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ralphvincent CA $166 CA $183 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Loro-Ciuffenna-Hotels-Villa-Cassia-Di-Baccano.h1130942.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/3000000/2700000/2690400/2690342/fd869ab3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2700000/2690400/2690342/c92d2813.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2700000/2690400/2690342/01ed134f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/3000000/2700000/2690400/2690342/d7d83723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### B&B La Fonte del Machiavelli [](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Bed-And-Breakfast-La-Fonte-Del-Machiavelli.h2690342.Hotel-Information) San Casciano in Val di Pesa 9.2/10 Wonderful (82 reviews) "It was a wonderful stay the bed was comfortable and the view was beautiful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ruben CA $168 CA $191 total includes taxes & fees Feb 2 - Feb 3 [](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Bed-And-Breakfast-La-Fonte-Del-Machiavelli.h2690342.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/23000000/22750000/22746400/22746331/994aad7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, soundproofing, free WiFi](https://images.trvl-media.com/lodging/23000000/22750000/22746400/22746331/2b26409c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/23000000/22750000/22746400/22746331/aba3f4d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/23000000/22750000/22746400/22746331/ddbdc210.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### L' Eroico [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-L-Eroico.h22746331.Hotel-Information) Gaiole in Chianti 10/10 Exceptional (12 reviews) "Monica was the friendliest most enthusiastic host we’ve stayed with. Everything from her greeting to the amazing breakfast was perfect. She does a lot of baking, so the breakfast was really a treat and you could also get eggs cooked in various ways. The room was a little small but very comfortable. Parking was on the street, but it was fairly close and easy." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Perry [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-L-Eroico.h22746331.Hotel-Information) ![Panoramic Apartment (2) | Terrace/patio](https://images.trvl-media.com/lodging/43000000/42410000/42405300/42405254/975fa997.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic Apartment (3)](https://images.trvl-media.com/lodging/43000000/42410000/42405300/42405254/24770db5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/43000000/42410000/42405300/42405254/36cba6ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic Apartment](https://images.trvl-media.com/lodging/43000000/42410000/42405300/42405254/4140baee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casa Vacanze Squarcialupi [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Casa-Vacanze-Squarcialupi.h42405254.Hotel-Information) Castellina in Chianti 8.8/10 Excellent (3 reviews) "Staff was very helpful. Was a bit bummed the pool was closed as that was part of the reason for choosing the hotel. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey CA $160 CA $186 total includes taxes & fees Feb 7 - Feb 8 [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Casa-Vacanze-Squarcialupi.h42405254.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/111000000/110880000/110872300/110872226/1f917275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Studio, Valley View](https://images.trvl-media.com/lodging/111000000/110880000/110872300/110872226/14afd628.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Studio, Valley View | Living area](https://images.trvl-media.com/lodging/111000000/110880000/110872300/110872226/59370526.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110880000/110872300/110872226/ac32e408.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Borgo Antico Residence [](https://www.expedia.ca/Certaldo-Hotels-Borgo-Antico-Residence.h110872226.Hotel-Information) Certaldo Alto 10/10 Exceptional (3 reviews) "Great place to relax take in the local culture and enjoy Tuscany." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) jane CA $104 CA $160 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Certaldo-Hotels-Borgo-Antico-Residence.h110872226.Hotel-Information) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/24000000/23190000/23183900/23183851/f58917b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/24000000/23190000/23183900/23183851/9c14d908.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Birthday party area](https://images.trvl-media.com/lodging/24000000/23190000/23183900/23183851/498c2bc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Duplex, 2 Bedrooms | Living area](https://images.trvl-media.com/lodging/24000000/23190000/23183900/23183851/cbaa7c02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Terre di Baccio [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Terre-Di-Baccio.h23183851.Hotel-Information) Greve in Chianti 9.8/10 Exceptional (71 reviews) "The stay was great, and the staff were wonderful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) SYDNEY [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Terre-Di-Baccio.h23183851.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/1000000/980000/971900/971821/967d2c05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/980000/971900/971821/ddee21d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/1000000/980000/971900/971821/4f478603.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor banquet area](https://images.trvl-media.com/lodging/1000000/980000/971900/971821/f623ffee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Antica Pieve B&B [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Antica-Pieve-BB.h971821.Hotel-Information) Barberino Tavarnelle 9.4/10 Exceptional (14 reviews) "Very nice stay here! Great breakfast and coffee every morning. Great location to tour around to different wineries and towns. Free parking. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Jessica CA $125 CA $176 total includes taxes & fees Feb 2 - Feb 3 [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Antica-Pieve-BB.h971821.Hotel-Information) ![Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/6000000/5340000/5331800/5331739/59068004.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5340000/5331800/5331739/03eeab0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/6000000/5340000/5331800/5331739/727e0d46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast meal](https://images.trvl-media.com/lodging/6000000/5340000/5331800/5331739/1d36a1bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relais Villa Belvedere [](https://www.expedia.ca/Figline-E-Incisa-Valdarno-Hotels-Relais-Villa-Belvedere.h5331739.Hotel-Information) Figline e Incisa Valdarno 9.2/10 Wonderful (70 reviews) "Very nice place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria CA $142 CA $158 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Figline-E-Incisa-Valdarno-Hotels-Relais-Villa-Belvedere.h5331739.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/96000000/95250000/95247500/95247428/265e303f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/96000000/95250000/95247500/95247428/a1551d86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free self parking](https://images.trvl-media.com/lodging/96000000/95250000/95247500/95247428/b0f5db83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/96000000/95250000/95247500/95247428/8275ba4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sportland [](https://www.expedia.ca/Colle-Di-Val-DElsa-Hotels-Sportland.h95247428.Hotel-Information) Colle di Val d'Elsa 7.2/10 Good (5 reviews) "Struttura essenziale ed economica " ![Italy](https://a.travel-assets.com/egds/marks/flags/it.svg) Giorgio [](https://www.expedia.ca/Colle-Di-Val-DElsa-Hotels-Sportland.h95247428.Hotel-Information) ![Panoramic Apartment](https://images.trvl-media.com/lodging/4000000/3630000/3620800/3620731/de61baae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![32-inch TV with cable channels](https://images.trvl-media.com/lodging/4000000/3630000/3620800/3620731/4f6d217b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3630000/3620800/3620731/b87dac4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/4000000/3630000/3620800/3620731/f41ed065.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residence Il Connubio [](https://www.expedia.ca/Impruneta-Hotels-Residence-Il-Connubio.h3620731.Hotel-Information) Impruneta 8.8/10 Excellent (32 reviews) "Such a cute little place! Very clean and easy to get around! Would highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Desiree [](https://www.expedia.ca/Impruneta-Hotels-Residence-Il-Connubio.h3620731.Hotel-Information) ![Family Apartment, 2 Bedrooms, Hill View, Tower | View from room](https://images.trvl-media.com/lodging/102000000/101940000/101930900/101930876/d8d59316.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Apartment, 2 Bedrooms, 2 Bathrooms, Courtyard View | Living area](https://images.trvl-media.com/lodging/102000000/101940000/101930900/101930876/56c25777.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Apartment, 2 Bedrooms, Non Smoking, Tower | Living area](https://images.trvl-media.com/lodging/102000000/101940000/101930900/101930876/24daf1d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/102000000/101940000/101930900/101930876/bd8eeebf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casa Vacanze Le Fornaci [](https://www.expedia.ca/Pergine-Valdarno-Hotels-Casa-Vacanze-Le-Fornaci.h101930876.Hotel-Information) Pergine Valdarno 9.4/10 Exceptional (3 reviews) "We absolutely loved our stay at this hotel. The suite was perfect and the restaurant had probably the best food I have had in Tuscany. We definitely plan to stay there again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gregory CA $178 CA $201 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Pergine-Valdarno-Hotels-Casa-Vacanze-Le-Fornaci.h101930876.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/3000000/2730000/2723600/2723529/4c3be6b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/3000000/2730000/2723600/2723529/c9ef69ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/3000000/2730000/2723600/2723529/36dbdc56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Memory foam beds, minibar, individually decorated](https://images.trvl-media.com/lodging/3000000/2730000/2723600/2723529/e7f84930.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa il Fedino [](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Villa-Il-Fedino.h2723529.Hotel-Information) San Casciano in Val di Pesa 9.6/10 Exceptional (97 reviews) "Great people, great location great service" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) James CA $188 CA $214 total includes taxes & fees Feb 12 - Feb 13 [](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Villa-Il-Fedino.h2723529.Hotel-Information) ![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) ![Property grounds](https://images.trvl-media.com/lodging/43000000/42410000/42405100/42405029/80b09a28.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) ### Agriturismo La Ferrozzola [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Agriturismo-La-Ferrozzola.h42405029.Hotel-Information) Castellina in Chianti 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) ![View from room](https://images.trvl-media.com/lodging/6000000/5280000/5273900/5273860/52973642.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/6000000/5280000/5273900/5273860/823021fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, 1 Double Bed (2 adults)](https://images.trvl-media.com/lodging/6000000/5280000/5273900/5273860/9d79efbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/6000000/5280000/5273900/5273860/b614c935.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chianti Village Morrocco [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Chianti-Village-Morrocco.h5273860.Hotel-Information) Barberino Tavarnelle 8.6/10 Excellent (111 reviews) "Spacious room in large resort style complex, set up as fully self contained with kitchen and dining furniture. Peaceful location with lovely views. Very pleasant staff and exceptional breakfast. " ![France](https://a.travel-assets.com/egds/marks/flags/fr.svg) Richard [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Chianti-Village-Morrocco.h5273860.Hotel-Information) ![Apartment | Exterior](https://images.trvl-media.com/lodging/90000000/89180000/89179500/89179420/59e23101.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment | Interior](https://images.trvl-media.com/lodging/90000000/89180000/89179500/89179420/15ad5902.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment | Interior](https://images.trvl-media.com/lodging/90000000/89180000/89179500/89179420/ff0d3da5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment | Dining](https://images.trvl-media.com/lodging/90000000/89180000/89179500/89179420/22f499bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Lux Apartment Chianti Firenze Area Italy [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Beautiful-Apartment-In-Chianti.h89179420.Hotel-Information) Barberino Tavarnelle CA $620 CA $757 total includes taxes & fees Jan 16 - Jan 17 [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Beautiful-Apartment-In-Chianti.h89179420.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/28000000/27400000/27397700/27397624/a64418f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/28000000/27400000/27397700/27397624/de3fa368.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room dining](https://images.trvl-media.com/lodging/28000000/27400000/27397700/27397624/d186b654.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/28000000/27400000/27397700/27397624/e1962a8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### B&B Le Dimore Mezza Costa [](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-BB-Le-Dimore-Mezza-Costa.h27397624.Hotel-Information) San Casciano in Val di Pesa 9.4/10 Exceptional (25 reviews) "The beautiful place, very comfortable, the incredible attention, the breakfast felt like in Homewith a lot of love We hope to return one day" ![Mexico](https://a.travel-assets.com/egds/marks/flags/mx.svg) Raymundo [](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-BB-Le-Dimore-Mezza-Costa.h27397624.Hotel-Information) ![Deluxe Room, City View](https://images.trvl-media.com/lodging/105000000/104550000/104540900/104540885/db32679d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, City View](https://images.trvl-media.com/lodging/105000000/104550000/104540900/104540885/6615ccb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/105000000/104550000/104540900/104540885/c24bbc8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/105000000/104550000/104540900/104540885/c2f130ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Maison Ginori Guelfa [](https://www.expedia.ca/Florence-Hotels-Maison-Ginori-Guelfa.h104540885.Hotel-Information) Historic Centre of Florence 10/10 Exceptional (21 reviews) "We loved everything about Maison Ginori Guelfa, from our host, our room and how close the walking distance to the center of the city." ![Australia](https://a.travel-assets.com/egds/marks/flags/au.svg) Janet CA $208 CA $249 total includes taxes & fees Jan 17 - Jan 18 [](https://www.expedia.ca/Florence-Hotels-Maison-Ginori-Guelfa.h104540885.Hotel-Information) ![Family Triple Room](https://images.trvl-media.com/lodging/20000000/19730000/19722800/19722799/afd8d18a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/20000000/19730000/19722800/19722799/f188ca9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/20000000/19730000/19722800/19722799/214c6915.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/20000000/19730000/19722800/19722799/f2f7037e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residenza La Musa Amarcord [](https://www.expedia.ca/Florence-Hotels-Residenza-La-Musa-Amarcord.h19722799.Hotel-Information) Historic Centre of Florence 9.8/10 Exceptional (153 reviews) "Room was large & well appointed. Bathroom was new with update products. Staff was great." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John [](https://www.expedia.ca/Florence-Hotels-Residenza-La-Musa-Amarcord.h19722799.Hotel-Information) ![Deluxe Double Room, City View | Room amenity](https://images.trvl-media.com/lodging/20000000/19420000/19411700/19411651/ce1860bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room, City View](https://images.trvl-media.com/lodging/20000000/19420000/19411700/19411651/ada72939.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/20000000/19420000/19411700/19411651/2a7cd831.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/20000000/19420000/19411700/19411651/e98a98d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### San Giuliano Inn - Adults Only [](https://www.expedia.ca/Florence-Hotels-San-Giuliano-Inn.h19411651.Hotel-Information) Historic Centre of Florence 10/10 Exceptional (406 reviews) "Great inn. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carol CA $128 CA $161 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Florence-Hotels-San-Giuliano-Inn.h19411651.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=2026-01-27&endDate=2026-01-28®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=2026-04-12&d1=2026-04-12&endDate=2026-04-15&d2=2026-04-15&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=2026-04-12&d1=2026-04-12&endDate=2026-04-15&d2=2026-04-15&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=2026-04-12&d1=2026-04-12&endDate=2026-04-15&d2=2026-04-15&lodging=RESIDENCE) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Chianti+Region%2C+Tuscany%2C+Italy®ionId=603148&latLong=43.534735%2C11.364917&adults=2&startDate=2026-04-12&d1=2026-04-12&endDate=2026-04-15&d2=2026-04-15&lodging=APART_HOTEL) 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=2026-04-12&d1=2026-04-12&endDate=2026-04-15&d2=2026-04-15&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=2026-04-12&d1=2026-04-12&endDate=2026-04-15&d2=2026-04-15&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=2026-04-12&d1=2026-04-12&endDate=2026-04-15&d2=2026-04-15&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=2026-04-12&d1=2026-04-12&endDate=2026-04-15&d2=2026-04-15&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=2026-04-12&d1=2026-04-12&endDate=2026-04-15&d2=2026-04-15&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-Vacation-Rentals.d603148.Travel-Guide-VacationRentals)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChianti-Region-Vacation-Rentals.d603148.Travel-Guide-VacationRentals) ## 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 niccolò & Spa](https://images.trvl-media.com/lodging/2000000/1290000/1289200/1289163/b8b0f4e2_y.jpg) ### Hotel Palazzo San niccolò & Spa 10/10 Excellent "One of the best hotels I’ve visited! " [](https://expedia.ca/Radda-In-Chianti-Hotels-Hotel-Palazzo-San-Niccolo.h1289163.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) ![COMO Castello Del Nero](https://images.trvl-media.com/lodging/2000000/1280000/1279800/1279768/5908bcb2_y.jpg) ### COMO Castello Del Nero 10/10 Excellent "Wonderful stay. 5-stars across the board if you’re looking for disconnecting and relaxing in the rolling hills of the Tuscan countryside. Easy day/dinner trips to Florence or Siena (rental car). " [](https://expedia.ca/Barberino-Tavarnelle-Hotels-COMO-Castello-Del-Nero.h1279768.Hotel-Information) ![Il Borro - Relais & Châteaux](https://images.trvl-media.com/lodging/6000000/5590000/5585700/5585638/4a6bd899_y.jpg) ### Il Borro - Relais & Châteaux 10/10 Excellent "A one of a kind, unique property amazing cuisine, and the tour we took of the wine cellar was the best I have ever experienced thanks to the helpfulness and knowledge of our guide Sophia" [](https://expedia.ca/Loro-Ciuffenna-Hotels-Il-Borro-Relais-Chateaux.h5585638.Hotel-Information) ## Find out more about Chianti Region You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded. As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chianti Region. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do. ## Explore a world of travel with Expedia - Recommended Vacation Rental Destinations - Trending destinations on Expedia.ca - All accommodation types in Chianti Region - [Province of Siena Vacation Rentals ](https://expedia.ca/Destinations-In-Province-Of-Siena.d6047850.Vacation-Rental-Destinations) - [Province of Florence Vacation Rentals ](https://expedia.ca/Destinations-In-Province-Of-Florence.d179893.Vacation-Rental-Destinations) - [Florence Vacation Rentals ](https://expedia.ca/Florence-Vacation-Rentals.d1222.Travel-Guide-VacationRentals) - [Province of Pisa Vacation Rentals ](https://expedia.ca/Destinations-In-Province-Of-Pisa.d6046818.Vacation-Rental-Destinations) - [Perugia Vacation Rentals ](https://expedia.ca/Perugia-Vacation-Rentals.d2762.Travel-Guide-VacationRentals) - [Province of Bologna Vacation Rentals ](https://expedia.ca/Destinations-In-Province-Of-Bologna.d6035254.Vacation-Rental-Destinations) - 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