Title: Chianti Region Vacation Rentals from CA $150: Short-Term Rentals for 2025 | 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 Tonight [Nov 28 - Nov 29](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-11-28&endDate=2025-11-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 29 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-11-29&endDate=2025-11-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-11-28&endDate=2025-11-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Vacation Rentals in Chianti Region ![2 bedrooms, cribs/infant beds, bed sheets](https://images.trvl-media.com/lodging/102000000/101510000/101503700/101503652/f6cba490.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bungalow](https://images.trvl-media.com/lodging/102000000/101510000/101503700/101503652/10c2f471.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/102000000/101510000/101503700/101503652/8027b728.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Chalet](https://images.trvl-media.com/lodging/102000000/101510000/101503700/101503652/e325c14e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### hu Firenze Certosa camping in town Impruneta 8.0/10 Very good (56) "Wonderful staff and great amenities!" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Chenjin [](https://www.expedia.ca/Impruneta-Hotels-Firenze-Certosa-Camping.h101503652.Hotel-Information) ![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) ![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) ![Property entrance](https://images.trvl-media.com/lodging/6000000/5280000/5273900/5273860/078ea232.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/6000000/5280000/5273900/5273860/156bd335.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chianti Village Morrocco Barberino Tavarnelle 8.6/10 Excellent (108) "Front desk was very helpful and very comfortable room. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Chianti-Village-Morrocco.h5273860.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/1000000/800000/797300/797278/c9efa80f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic Suite, Garden View | Living area](https://images.trvl-media.com/lodging/1000000/800000/797300/797278/50c585d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/800000/797300/797278/e66754fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/800000/797300/797278/b741acfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relais Villa Olmo Impruneta 9.4/10 Exceptional (227) "This is a beautiful Villa with a stunning views. Rooms were large and very clean and the location was wonderful. It was close to Florence and ideal for exploring Tuscany. Restaurant offered delicious buffet breakfast and many other wonderful local dishes for lunch and dinner. I would highly recommend this Villa and would love to stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ewa [](https://www.expedia.ca/Impruneta-Hotels-Relais-Villa-Olmo.h797278.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/20000000/19150000/19149200/19149185/3c3d9142.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, stereo](https://images.trvl-media.com/lodging/20000000/19150000/19149200/19149185/3005f289.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/20000000/19150000/19149200/19149185/9f090477.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, stereo](https://images.trvl-media.com/lodging/20000000/19150000/19149200/19149185/816a4ba5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Farmhouse in the heart of the real chiantishire Castellina in Chianti 10/10 Exceptional (147) "We loved our stay! The Farmhouse is really lovely and the view out the back is exceptional. We enjoyed a lot of home cooked meals with the most stunning view. Daniele was amazing to communicate with as well. Definitely hope to be back one day! " ![Australia](https://a.travel-assets.com/egds/marks/flags/au.svg) Rebekah T. [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Farmhouse-In-The-Heart-Of-The-Real-Chiantishire.h19149185.Hotel-Information) ![Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/6000000/5340000/5331800/5331739/13c851d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Apartment, 2 Bedrooms, Non Smoking, Garden View | View from room](https://images.trvl-media.com/lodging/6000000/5340000/5331800/5331739/94007780.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Apartment, 2 Bedrooms, Non Smoking | Private kitchen](https://images.trvl-media.com/lodging/6000000/5340000/5331800/5331739/9a487d30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/6000000/5340000/5331800/5331739/ffdc0f34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relais Villa Belvedere Figline e Incisa Valdarno 9.2/10 Wonderful (69) "Very nice place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria CA $134 CA $150 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Figline-E-Incisa-Valdarno-Hotels-Relais-Villa-Belvedere.h5331739.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/19000000/18770000/18768700/18768614/7adfb34e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/19000000/18770000/18768700/18768614/be3a90be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/19000000/18770000/18768700/18768614/3b7932fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18770000/18768700/18768614/7e5228ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### CHRISTMAS OFFER!10% DISCOUNT! Charming Villa Torre in Chianti, 8ensuite bedrooms San Casciano in Val di Pesa 10/10 Exceptional (124) "Excellent property Great bedrooms and eating area" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) douglas f. [](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Charming-Villa-Torre-In-Chianti.h18768614.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/31000000/30360000/30357400/30357304/266fd5bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/31000000/30360000/30357400/30357304/4e759628.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/31000000/30360000/30357400/30357304/f6bec757.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/31000000/30360000/30357400/30357304/c3290bf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa with large garden in the Chianti hills Siena 9.6/10 Exceptional (75) "Our group enjoyed staying in this location. It was comfortable and a perfect central location for exploring Tuscany." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica P. [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Villa-With-Large-Garden-In-The-Chianti-Hills.h30357304.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/19000000/19000000/18992900/18992864/d17810d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/19000000/18992900/18992864/8a99975c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/19000000/18992900/18992864/4630dd1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/19000000/19000000/18992900/18992864/a7397929.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi Montespertoli 9.4/10 Exceptional (66) "Check in smoothHost helpfulBeds comfortable.Perfect for a 2 week vacation for 21 family members.Close to major tourist attractions.Pool area very frequently used,the kids loved it.Evenings spent talking in the court yard were lovely.Chef Loradena's cooking class at the house in the industrial kitchen was a hit with all.P" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elisabeth R. [](https://www.expedia.ca/Montespertoli-Hotels-Villa-Between-Florence-Siena-And-Pisa-1-Km-To-Village-AC-In-All-Rooms-Wi-Fi.h18992864.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33960000/33956800/33956712/f1536fdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool, sun loungers](https://images.trvl-media.com/lodging/34000000/33960000/33956800/33956712/65e72921.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, Netflix, DVD player](https://images.trvl-media.com/lodging/34000000/33960000/33956800/33956712/361cf923.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/34000000/33960000/33956800/33956712/73cc2cee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa with concierge service & heated pool at 20 minute from Florence center impruneta 10/10 Exceptional (105) "Our host (Cate), along with her sister and mother, were fantastic. Very responsive, easy to get ahold of and worked very hard to ensure our visit was amazing. Cate was onsite and worked closely with the catering company and made sure all went well.." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Tom A. CA $1,904 CA $2,183 total includes taxes & fees Nov 29 - Nov 30 [](https://www.expedia.ca/Impruneta-Hotels-Tailored-To-YouVilla-Wheated-Pool-And-Concierge-Only-8-Mile-To-Florence-Center.h33956712.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/4000000/3530000/3522800/3522769/e2d4f39b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch, dinner served; local cuisine, garden views ](https://images.trvl-media.com/lodging/4000000/3530000/3522800/3522769/7e32286c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Apartment, 1 Queen Bed, Hill View, Ground Floor](https://images.trvl-media.com/lodging/4000000/3530000/3522800/3522769/6368a112.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/4000000/3530000/3522800/3522769/6e42344d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Riserva di Fizzano Residence Castellina in Chianti 9.8/10 Exceptional (23) "Perfect location on the top of a hill surrounded by the beautiful vineyards of Chianti. Enjoy the view by the pool or the fabulous sunset with a glass of wine. The staff were friendly and the restaurant was 5 star. I highly recommend a stay to fulfill all your Tuscan dreams. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eileen [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Riserva-Di-Fizzano-Residence.h3522769.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/20000000/19400000/19392600/19392539/80240ac7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, books, stereo](https://images.trvl-media.com/lodging/20000000/19400000/19392600/19392539/e221f421.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, books, stereo](https://images.trvl-media.com/lodging/20000000/19400000/19392600/19392539/3b834f1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/20000000/19400000/19392600/19392539/ee32f64a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### PICTURESQUE VIEWS OLIVE VINEYARDS EAT DRINK PURE RECREATION Ruffoli 9.8/10 Exceptional (59) "Great location in the heart Chianti. The host was very welcoming and the apartment was perfect. very comfortable bed and very quiet location. Nice terrace and pool but unfortunately the weather wasnt warm enough for us to enjoy the pool. There is a dirt road to get to the apartment but very easy to navigate so dont be worried about it. Thank you Babette, we hope to have the pleasure of going back sometime." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andre P. [](https://www.expedia.ca/Greve-In-Chianti-Hotels-PICTURESQUE-VIEWS-OLIVE-VINEYARDS-EAT-DRINK-PURE-RECREATION.h19392539.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/92000000/91100000/91097500/91097415/aa901301.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/92000000/91100000/91097500/91097415/23551d12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/92000000/91100000/91097500/91097415/f353b156.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/92000000/91100000/91097500/91097415/8a59c231.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stunning villa for 6 guests with private pool, WIFI, A/C, TV, patio and pets allowed Cavriglia 10/10 Exceptional (13) "Really great stay here.The villa is absolutely beautiful on the outside and inside.Parking was easy (right in front of property).Location was beautiful and hosts were great." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mohammed S. [](https://www.expedia.ca/Cavriglia-Hotels-Wonderful-Villa-For-6-Guests-With-AC.h91097415.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/3000000/2530000/2523800/2523707/deea12d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2530000/2523800/2523707/174b4f16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/3000000/2530000/2523800/2523707/5d2f1a55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/3000000/2530000/2523800/2523707/d197edf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Il Palagio Rignano sull'Arno 8.6/10 Excellent (60) "The best place in the region" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Kamen [](https://www.expedia.ca/Rignano-SullArno-Hotels-Villa-Il-Palagio.h2523707.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/19000000/18770000/18760900/18760840/cd8d91ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18770000/18760900/18760840/d32a44ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18770000/18760900/18760840/fd9dd70d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![11 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/19000000/18770000/18760900/18760840/d808b9e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views Castellina in Chianti 10/10 Exceptional (64) "Gorgeous property - we had a wonderful stay " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Michelle D. [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Isola-Serena-New-Private-Luxury-Villa-Chianti-Pool-Stunning-Views.h18760840.Hotel-Information) ![Interior detail](https://images.trvl-media.com/lodging/11000000/10390000/10386200/10386149/94f3c761.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic Apartment, 4 Bedrooms (Refrigerator,Galleria) | Living area](https://images.trvl-media.com/lodging/11000000/10390000/10386200/10386149/c93c8969.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/11000000/10390000/10386200/10386149/8d24db13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic Apartment, 4 Bedrooms (Refrigerator,Galleria)](https://images.trvl-media.com/lodging/11000000/10390000/10386200/10386149/28d72b99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castello di Montegufoni Montespertoli 8.0/10 Very good (31) "This was a stunning castle to stay in. The frescoed ceilings were gorgeous. Loved every minute that we were there. The staff were wonderful. The only thing i would recommend is to add a vending machine and maybe to offer pastries in thr morning. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cheryl [](https://www.expedia.ca/Montespertoli-Hotels-Castello-Di-Montegufoni.h10386149.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/17000000/16160000/16157300/16157250/32284d0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Poolside bar](https://images.trvl-media.com/lodging/17000000/16160000/16157300/16157250/789c7666.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mobile Home Deluxe | Terrace/patio](https://images.trvl-media.com/lodging/17000000/16160000/16157300/16157250/9b90d038.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/17000000/16160000/16157300/16157250/b4cc24c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Camping Village Il Poggetto Rignano sull'Arno 8.0/10 Very good (65) "Second stay at this property but got a 3 bed 2 bath cabin this time. Happy with most things could have had more housekeeping for a ten day stay. Great base to explore Tuscany excellent bar especially the staff as well as a nice restaurant " ![Australia](https://a.travel-assets.com/egds/marks/flags/au.svg) Rebecca [](https://www.expedia.ca/Rignano-SullArno-Hotels-Camping-Village-Il-Poggetto.h16157250.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/7000000/6360000/6359500/6359426/be420108.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/7000000/6360000/6359500/6359426/718c66e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/7000000/6360000/6359500/6359426/3d6cda97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 2 Bedrooms, Patio (Chianti)](https://images.trvl-media.com/lodging/7000000/6360000/6359500/6359426/ea5953bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castello Del Nero - Podere San Filippo Barberino Tavarnelle 9.8/10 Exceptional (38) "Much nicer stay then the rooms at the Como" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Podere-San-Filippo.h6359426.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/28000000/27480000/27478100/27478003/7e4aed19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/28000000/27480000/27478100/27478003/cafe3d68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, table tennis, stereo](https://images.trvl-media.com/lodging/28000000/27480000/27478100/27478003/68193f32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/28000000/27480000/27478100/27478003/efc1333d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wonderful Villa - Air Bubble Massage Pool - WiFi - max.14peopl Greve in Chianti (Firenze) 10/10 Exceptional (42) "Elena and her staff were excellent. They provided us with a welcome dinner which was great after our long trip in, as well as breakfast the next morning. Property is beautiful up in top of a hill overlooking the beautiful landscape. We had 9 people with more than enough room for all of us. Highly recommended!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ryan F. [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Wonderful-Villa-Air-Bubble-Massage-Pool-WiFi-Max14peopl.h27478003.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/41000000/40900000/40894800/40894778/819919b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, in-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/41000000/40900000/40894800/40894778/1bde548f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels, soap, shampoo](https://images.trvl-media.com/lodging/41000000/40900000/40894800/40894778/w1103h1598x0y0-372f03af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/41000000/40900000/40894800/40894778/fc5f2ab3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Romantic house in the middle of the Chianti vineyards in the heart of Tuscany. Greve in Chianti 9.0/10 Wonderful (24) "Wonderful house with all the facilities you need for self-catering. Although we used it as a base to visit all around the area, we also spent a few days just relaxing in the garden and going to the pool.Well equipped kitchen including a dishwasher and washing machine.Very peacefu, would love to come back one day." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert H. [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Vrbo-Property.h40894778.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/30000000/29750000/29741600/29741545/187dffc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/30000000/29750000/29741600/29741545/9b665b5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/30000000/29750000/29741600/29741545/60589de1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/30000000/29750000/29741600/29741545/ccecd19f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Your panoramic house in Tuscany between vineyards and olive groves. Barberino Val d'Elsa 9.8/10 Exceptional (43) "The property was absolutely charming. It really had that homey, Italian, Tuscan charm about it. The kids and my husband loved it too. I wish I had planned for more days there. We didn’t have time to partake in the cooking class or truffle hunting, but I guess that just leaves a reason to come back. The location was great too because it’s in the country away from the busy cities, but a close enough drive to all the various Tuscan sites.The owners were very nice and spoke good enough English.... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gwen L. [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Your-Panoramic-House-In-Tuscany-Between-Vineyards-And-Olive-Groves.h29741545.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-12&endDate=2025-12-13®ionId=603148&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=VR_BF_PROMO_603148) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChianti-Region-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 ![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 di Fonterutoli Wine Resort](https://images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/9f05cf5a_y.jpg) ### Castello di Fonterutoli Wine Resort 10/10 Excellent "Amazing experience! The staff were very knowledgeable and helpful in setting up our dinner and wine tour. Room had a beautiful view. This was the best part of our journey through Italy. Keep up the great work! A+ " [](https://expedia.ca/Castellina-In-Chianti-Hotels-Castello-Di-Fonterutoli.h5172395.Hotel-Information) ![Salvadonica - Borgo del Chianti](https://images.trvl-media.com/lodging/21000000/20490000/20484000/20483959/56ce48bb_y.jpg) ### Salvadonica - Borgo del Chianti 10/10 Excellent "Great staff, great room and amenities. Outstanding romantic Tuscany location. Going back again." [](https://expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Salvadonica.h20483959.Hotel-Information) ![Hotel Palazzo San Lorenzo & SPA](https://images.trvl-media.com/lodging/4000000/3480000/3475000/3474921/1af45070_y.jpg) ### Hotel Palazzo San Lorenzo & SPA 10/10 Excellent "Beautiful hotel and spa. Excellent amenities and modern luxuries. " [](https://expedia.ca/Colle-Di-Val-DElsa-Hotels-Hotel-Palazzo-San-Lorenzo-SPA.h3474921.Hotel-Information) ![Villa I Barronci Resort & Spa](https://images.trvl-media.com/lodging/3000000/2530000/2523800/2523750/d7de1ccd_y.jpg) ### Villa I Barronci Resort & Spa 10/10 Excellent "Stayed here as part of our honeymoon. Staff were super helpful with reservations and recommendations. The view is beautiful and the rooms are cozy. The breakfast was delicious as well." [](https://expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Villa-I-Barronci-Resort-Spa.h2523750.Hotel-Information) ![Hotel Borgo di Cortefreda Relais](https://images.trvl-media.com/lodging/2000000/1220000/1216500/1216478/288cff0c_y.jpg) ### Hotel Borgo di Cortefreda Relais 10/10 Excellent "The staff at the front desk was amazing. When we arrived he greeted us with such a warm smile and welcomed us to the hotel. He absolutely made the hotel experience much better. " [](https://expedia.ca/Barberino-Tavarnelle-Hotels-Hotel-Borgo-Di-Cortefreda-Relais.h1216478.Hotel-Information) ![Villa Castiglione](https://images.trvl-media.com/lodging/2000000/1350000/1348200/1348125/dbdc1d6b_y.jpg) ### Villa Castiglione 10/10 Excellent "Nice and cute place. Great price. " [](https://expedia.ca/Impruneta-Hotels-Villa-Castiglione.h1348125.Hotel-Information) ![COMO Castello Del Nero](https://images.trvl-media.com/lodging/2000000/1280000/1279800/1279768/5908bcb2_y.jpg) ### COMO Castello Del Nero 10/10 Excellent "Wonderful stay. 5-stars across the board if you’re looking for disconnecting and relaxing in the rolling hills of the Tuscan countryside. Easy day/dinner trips to Florence or Siena (rental car). " [](https://expedia.ca/Barberino-Tavarnelle-Hotels-COMO-Castello-Del-Nero.h1279768.Hotel-Information) ![Il Borro - Relais & Châteaux](https://images.trvl-media.com/lodging/6000000/5590000/5585700/5585638/4a6bd899_y.jpg) ### Il Borro - Relais & Châteaux 10/10 Excellent "A one of a kind, unique property amazing cuisine, and the tour we took of the wine cellar was the best I have ever experienced thanks to the helpfulness and knowledge of our guide Sophia" [](https://expedia.ca/Loro-Ciuffenna-Hotels-Il-Borro-Relais-Chateaux.h5585638.Hotel-Information) ## 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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[Car rentals near Port of Livorno](https://expedia.ca/Car-Rentals-In-Port-Of-Livorno.d6190962.Car-Rental-Guide) Activities - [Things to do in Amalfi Coast](https://expedia.ca/Things-To-Do-In-Amalfi-Coast.d180060.Travel-Guide-Activities) - [Things to do in Castiglioncello](https://expedia.ca/Things-To-Do-In-Castiglioncello.d6034140.Travel-Guide-Activities) - [Things to do in Sorrento Coast](https://expedia.ca/Things-To-Do-In-Sorrento-Coast.d6059422.Travel-Guide-Activities) Packages - [Amalfi Coast All-inclusive Vacation Packages](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations/180060/Amalfi-Coast) - [Capri Island Vacations](https://expedia.ca/Capri-Island.d180062.Destination-Travel-Guides) - [Terme di Saturnia](https://expedia.ca/Terme-Di-Saturnia-Manciano.d6150383.Vacation-Attraction) - [Amalfi Coast Vacations](https://expedia.ca/Amalfi-Coast.d180060.Destination-Travel-Guides) - [Cinque Terre National Park Vacations](https://expedia.ca/Cinque-Terre-National-Park.d180063.Destination-Travel-Guides) Vacation Rentals - [Amalfi Coast Vacation Rentals](https://expedia.ca/Amalfi-Coast-Vacation-Rentals.d180060.Travel-Guide-VacationRentals) General - [Visit Capri Island](https://expedia.ca/Capri-Island.dx180062) - [Visit Porto Santo Stefano](https://expedia.ca/Porto-Santo-Stefano.dx6025634) - [Visit Talamone](https://expedia.ca/Talamone.dx6049866) - [Visit Santa Maria Novella](https://expedia.ca/Florence-Santa-Maria-Novella.dx6084343) - [Visit Sorrento Coast](https://expedia.ca/Sorrento-Coast.dx6059422) - [Visit Elba Island](https://expedia.ca/Elba-Island.dx1090) - [Visit Palermo Coast](https://expedia.ca/Palermo-Coast.dx6084705) - [Visit Pisa City Centre](https://expedia.ca/Pisa-Pisa-City-Centre.dx553248633938945235) - [Visit Brunello di Montalcino Wine Area](https://expedia.ca/Brunello-Di-Montalcino-Wine-Area.dx6342620) - [Visit Amalfi Coast](https://expedia.ca/Amalfi-Coast.dx180060) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)