Title: Chianti Region Vacation Rentals from CA $78: 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://a.travel-assets.com/findyours-php/viewfinder/images/res70/157000/157505-Chianti-Region.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Chianti Region Vacation Rentals ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-11-21&endDate=2025-11-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-01-16&endDate=2026-01-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Vacation Rentals in Chianti Region ![Exterior](https://images.trvl-media.com/lodging/4000000/3540000/3530100/3530075/dcea3a98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Chalet | Private kitchen](https://images.trvl-media.com/lodging/4000000/3540000/3530100/3530075/3c496c9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio](https://images.trvl-media.com/lodging/4000000/3540000/3530100/3530075/27bf5fc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Highchair](https://images.trvl-media.com/lodging/4000000/3540000/3530100/3530075/2a21ee53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hu Norcenni Girasole Village Figline e Incisa Valdarno 8.6/10 Excellent (304) "Great friendly fun camp site" CA $68 CA $78 total includes taxes & fees Sep 24 - Sep 25 [](https://www.expedia.ca/Figline-E-Incisa-Valdarno-Hotels-Norcenni-Girasole-Village.h3530075.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) ![1 bedroom, 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) ![View from property](https://images.trvl-media.com/lodging/17000000/16160000/16157300/16157250/e496b256.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) ### Camping Village Il Poggetto Rignano sull'Arno 8.0/10 Very good (60) "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 " CA $84 CA $96 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Rignano-SullArno-Hotels-Camping-Village-Il-Poggetto.h16157250.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/800000/797300/797278/36e10829.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) ![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) ### Relais Villa Olmo Impruneta 9.4/10 Exceptional (223) "Wonderful stay- we really enjoyed our stay and did not want to leave!! Beautiful hotel and wonderful service!" CA $335 CA $374 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Impruneta-Hotels-Relais-Villa-Olmo.h797278.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) ![Property entrance](https://images.trvl-media.com/lodging/6000000/5280000/5273900/5273860/078ea232.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) ![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 (103) "Front desk was very helpful and very comfortable room. " CA $112 CA $127 total includes taxes & fees Sep 27 - Sep 28 [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Chianti-Village-Morrocco.h5273860.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) ![Property grounds](https://images.trvl-media.com/lodging/19000000/18770000/18760900/18760840/7066b059.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) ![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) ### ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views Castellina in Chianti 10/10 Exceptional (63) "We had booked the villa for our wedding week to host 23 of our closest friends and family. It exceeded expectations in everyway, the views are breathtaking, the outside living areas are perfect for hosting large lunches and dinners, all the rooms are beautiful, and Raffaella and her team made sure we had everything we needed and more during our stay. It is so peaceful and quiet to enjoy the true beauty of Tuscany but also so close to the local town for dinners and shopping. The list of... [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Isola-Serena-New-Private-Luxury-Villa-Chianti-Pool-Stunning-Views.h18760840.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) ![Courtyard](https://images.trvl-media.com/lodging/6000000/5340000/5331800/5331739/ffdc0f34.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) ### Relais Villa Belvedere Figline e Incisa Valdarno 9.2/10 Wonderful (67) "Beautiful apartments and grounds with lovely views, Every one was very helpful and friendly. breakfast was very good, wish we could have stayed longer." CA $136 CA $153 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Figline-E-Incisa-Valdarno-Hotels-Relais-Villa-Belvedere.h5331739.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/31000000/30360000/30357400/30357304/b10e2694.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) ![Outdoor pool](https://images.trvl-media.com/lodging/31000000/30360000/30357400/30357304/4e759628.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa with large garden in the Chianti hills Siena 9.6/10 Exceptional (72) "Our group enjoyed staying in this location. It was comfortable and a perfect central location for exploring Tuscany." [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Villa-With-Large-Garden-In-The-Chianti-Hills.h30357304.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) ![Property grounds](https://images.trvl-media.com/lodging/19000000/18770000/18768700/18768614/3b7932fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/19000000/18770000/18768700/18768614/a852118a.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) ### Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C. San Casciano in Val di Pesa 10/10 Exceptional (118) "We spent 2 weeks in this beautiful villa with close access to Florence and the easy trains of Italy. Bea and Jacapo were wonderful hosts and meals at the villa were delicious. The pool was a great relief at the end of warm and busy traveling days. We highly recommend this beautiful villa. " [](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Charming-Villa-Torre-In-Chianti.h18768614.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/43000000/42410000/42405100/42405029/3584552d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 Bedroom, Kitchenette (Iris)](https://images.trvl-media.com/lodging/43000000/42410000/42405100/42405029/eb2dffec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 Bedroom, Kitchenette (Iris) | Private kitchen](https://images.trvl-media.com/lodging/43000000/42410000/42405100/42405029/a0c7f7fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/43000000/42410000/42405100/42405029/313690ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Agriturismo La Ferrozzola Castellina in Chianti 9.4/10 Exceptional (9) "Very nice agriturismo. " [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Agriturismo-La-Ferrozzola.h42405029.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) ![Exterior](https://images.trvl-media.com/lodging/4000000/3530000/3522800/3522769/6901a1c5.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) ![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) ### Riserva di Fizzano Residence Castellina in Chianti 9.8/10 Exceptional (22) "We had 2 beautiful days here in Chianti. Lovely property with a very good restaurant. Stunning views over the vineyards and Tuscany hills. Close drive to interesting cites. And the wine.... love to come back, and can absolutely recomend a stay here." CA $280 CA $312 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Riserva-Di-Fizzano-Residence.h3522769.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) ![Outdoor dining](https://images.trvl-media.com/lodging/20000000/19150000/19149200/19149185/c265eef8.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 (142) "What a view! This location was all that we were hoping for. Thank you! " [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Farmhouse-In-The-Heart-Of-The-Real-Chiantishire.h19149185.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) ![Reception](https://images.trvl-media.com/lodging/3000000/2530000/2523800/2523707/d197edf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/3000000/2530000/2523800/2523707/8f10a5fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Il Palagio Rignano sull'Arno 8.4/10 Very good (58) "We stayed 2 nights and loved it! We have a 2 bedroom , 2 bath apartment and it was so spacious. We enjoyed the kind staff and the breakfast had a lot of choices. It was great" CA $118 CA $135 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Rignano-SullArno-Hotels-Villa-Il-Palagio.h2523707.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/30000000/29750000/29741600/29741545/60589de1.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) ![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 (40) "Very spacious and clean villa in between Florence and Siena in the heart of Chianti. Tremendous hosts that communicated often and met a couple special requests. Have already referred this listing and will definitely come back!" [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Your-Panoramic-House-In-Tuscany-Between-Vineyards-And-Olive-Groves.h29741545.Hotel-Information) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/7000000/6360000/6359500/6359426/3d6cda97.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) ![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 10/10 Exceptional (37) "Much nicer stay then the rooms at the Como" [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Podere-San-Filippo.h6359426.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34140000/34139100/34139023/1d675416.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34140000/34139100/34139023/5d98ae7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/35000000/34140000/34139100/34139023/57888d87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34140000/34139100/34139023/abb7f18e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Exclusive 7BR-8BA Villa with pool, a few mins from town, yet in the countryside Impruneta 10/10 Exceptional (80) "Our family of eight spent twelve days at Villa Le Colline. The Villa was the perfect location from which to tour various areas of Italy. We could not have been more pleased. The home, grounds and views are much more beautiful than the pictures showed! It was a wonderful stay, and we would highly recommend this Villa for large families spending several days in the area. " [](https://www.expedia.ca/Impruneta-Hotels-Exclusive-7BR-8BA-Villa-With-Pool.h34139023.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/12000000/11810000/11807600/11807517/cc572805.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Buffet](https://images.trvl-media.com/lodging/12000000/11810000/11807600/11807517/c96d8943.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/12000000/11810000/11807600/11807517/bfdf14a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room Single Use, 1 Queen Bed, Balcony, Hill View | View from room](https://images.trvl-media.com/lodging/12000000/11810000/11807600/11807517/3f8ec422.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Palazzo Pacini Colle di Val d'Elsa 9.8/10 Exceptional (95) "We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food " CA $210 CA $234 total includes taxes & fees Sep 30 - Oct 1 [](https://www.expedia.ca/Colle-Di-Val-DElsa-Hotels-Palazzo-Pacini.h11807517.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/11000000/10390000/10386200/10386149/8d24db13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castello di Montegufoni Montespertoli 8.2/10 Very good (29) "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. " [](https://www.expedia.ca/Montespertoli-Hotels-Castello-Di-Montegufoni.h10386149.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) ![Interior](https://images.trvl-media.com/lodging/28000000/27480000/27478100/27478003/efc1333d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, table tennis, stereo](https://images.trvl-media.com/lodging/28000000/27480000/27478100/27478003/4913a3ab.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) ### Wonderful Villa - Air Bubble Massage Pool - WiFi - max.14peopl Greve in Chianti (Firenze) 10/10 Exceptional (41) "We celebrated our 25th wedding anniversary with friends. It was a beautiful property with the most amazing views. This family owned and operated property was well taken care of. The service was exceptional." [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Wonderful-Villa-Air-Bubble-Massage-Pool-WiFi-Max14peopl.h27478003.Hotel-Information) ![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) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/40000000/39680000/39673400/39673326/958cb39c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, oven, stovetop, espresso maker](https://images.trvl-media.com/lodging/40000000/39680000/39673400/39673326/48f7d2f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/40000000/39680000/39673400/39673326/252d70f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rocca Palazzaccio Impruneta 9.0/10 Wonderful (13) "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... CA $96 CA $110 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Impruneta-Hotels-Rocca-Palazzaccio.h39673326.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) ![Exterior](https://images.trvl-media.com/lodging/19000000/19000000/18992900/18992864/4630dd1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/19000000/19000000/18992900/18992864/dfaac6d3.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) "The Leoni Villa is the perfect spot for a family vacation. There were 14 of us from 2 years old to 65 years old and we all had a great time! The rooms are great as well as the grounds which offers lemon, plum and olive trees. The Villa also has a spectacular pool with great views. Marco the caretaker was wonderful and helped us with anything we needed." [](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) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-06&endDate=2025-10-07®ionId=603148&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChianti-Region-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 Borgo di Cortefreda Relais](//images.trvl-media.com/lodging/2000000/1220000/1216500/1216478/288cff0c_y.jpg) ### Hotel Borgo di Cortefreda Relais 10/10 Excellent "We really enjoyed our honeymoon suite. We would definitely recommend this spot." [](https://expedia.ca/Barberino-Tavarnelle-Hotels-Hotel-Borgo-Di-Cortefreda-Relais.h1216478.Hotel-Information) ![Castello di Spaltenna- Small Luxury Hotels of the World](//images.trvl-media.com/lodging/3000000/2550000/2540800/2540741/75ac6194_y.jpg) ### Castello di Spaltenna- Small Luxury Hotels of the World 10/10 Excellent "Of all the beautiful places we stayed on our Italy trip, this was, hands down our favorite. From the moment we pulled up, we were met by staff to take our luggage and drive us to the reception area for check in. We were greeted by a friendly staff members, given a tour of the property and information we might need for our stay. The property is breathtakingly stunning. Our room was absolutely beautiful and the perfect blend of luxury and rustic, Tuscan charm. The dinner we had at one of their restaurants was incredible and the staff attentive in the best way possible- while allowing us the time to savor the delicious meal, converse and just take in all the beautiful atmosphere. We booked time together at their Spa, which we enjoyed, and my husband had a relaxing sports massage. The breakfast in the morning had the greatest variety, attentive staff and quality choices that we have ever experienced. We can’t recommend Castelló di Spaltenna enough, truly a magical place, nestled in the heart of the Chianti region." [](https://expedia.ca/Gaiole-In-Chianti-Hotels-Castello-Di-Spaltenna.h2540741.Hotel-Information) ![hu Firenze Certosa camping in town](//images.trvl-media.com/lodging/102000000/101510000/101503700/101503652/f6cba490_y.jpg) ### hu Firenze Certosa camping in town 10/10 Excellent "Overall I liked everything " [](https://expedia.ca/Impruneta-Hotels-Firenze-Certosa-Camping.h101503652.Hotel-Information) ![Hotel Villa Campomaggio](//images.trvl-media.com/lodging/4000000/3610000/3605900/3605816/f6f6c579_y.jpg) ### Hotel Villa Campomaggio 10/10 Excellent "A perfect stay, we wish we booked more nights! Gorgeous property, quiet grounds and even better massages and facials done by the best, Julia! We will come back!" [](https://expedia.ca/Radda-In-Chianti-Hotels-Hotel-Villa-Campomaggio.h3605816.Hotel-Information) ![Salvadonica - Borgo del Chianti](//images.trvl-media.com/lodging/21000000/20490000/20484000/20483959/56ce48bb_y.jpg) ### Salvadonica - Borgo del Chianti 10/10 Excellent "This stay exceeded my expectations! A beautiful location, great food with an excellent breakfast included, and tons of well-planned experiences for the guests. This stay was one of my favorites out of my entire trip" [](https://expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Salvadonica.h20483959.Hotel-Information) ![Hu Norcenni Girasole Village](//images.trvl-media.com/lodging/4000000/3540000/3530100/3530075/dcea3a98_y.jpg) ### Hu Norcenni Girasole Village 10/10 Excellent "Clean pool, everything within easy reach, beautiful rooms, lovely staff, my only concern was the lack of a kettle in the room- this was managable but I'd say a kettle is more universal that an espresso maker. Take bug bite spray though- the bugs ate me alive due to being in the hills, but still one of the best places with everything being near. The little road train was fabulous! Its made me want to book another break with Hu! " [](https://expedia.ca/Figline-E-Incisa-Valdarno-Hotels-Norcenni-Girasole-Village.h3530075.Hotel-Information) ![Villa I Barronci Resort & Spa](//images.trvl-media.com/lodging/3000000/2530000/2523800/2523750/d7de1ccd_y.jpg) ### Villa I Barronci Resort & Spa 10/10 Excellent "Wonderful place to stay to soak in the views of Tuscany. The pool area with views are gorgeous. Breakfast was fantastic. Rooms were clean, property was quiet. There are a lot of dining options a 10 min drive away in the town of San Casciano. You definately need a car here. Absoltuely wonderful stay, the highlight of my trip!" [](https://expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Villa-I-Barronci-Resort-Spa.h2523750.Hotel-Information) ![Torre a Cona Wine Estate](//images.trvl-media.com/lodging/43000000/42060000/42059900/42059842/aaf98c1b_y.jpg) ### Torre a Cona Wine Estate 10/10 Excellent "It’s hard to know where to begin when describing this property, but I guess I have to start somewhere. This is quite possibly the most beautiful property I’ve ever had the pleasure to visit. The grounds are exceptionally gorgeous. The food is mind-blowingly excellent. The wine superb. The service incredible. We had the best time at our cooking class as we were grouped with 8 strangers who became friends by the end of the evening. The pool is enchanting, the room was huge and impeccably appointed. Wow. Wow. Wow. I will miss my time at Torre A Cona!" [](https://expedia.ca/Rignano-SullArno-Hotels-Torre-A-Cona-Wine-Estate.h42059842.Hotel-Information) ![Castello di Fonterutoli Wine Resort](//images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/9f05cf5a_y.jpg) ### Castello di Fonterutoli Wine Resort 10/10 Excellent "Really nice, quiet, next to the vineyard. " [](https://expedia.ca/Castellina-In-Chianti-Hotels-Castello-Di-Fonterutoli.h5172395.Hotel-Information) ## Find out more about Chianti Region **Everything you need to know about** **Chianti Region** **vacation rentals** Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chianti Region vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on! There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chianti Region vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.  **Chianti Region vacation rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Chianti Region. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in .  Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chianti Region vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chianti Region vacation rentals we have selected for you start as low as CA $78 per night. Entering your travel dates in the search wizard you might find even better deals! **How to find incredible deals on Chianti Region rentals** At Expedia, we put the best Chianti Region vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.  To find some top Chianti Region rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chianti Region vacation. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chianti Region. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.  ## 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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)