Title: Book the Best Chianti Region Hotels with FREE PARKING in 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)[Vacation Rentals in Chianti Region](https://expedia.ca/Chianti-Region-Vacation-Rentals.d603148.Travel-Guide-VacationRentals)[Flights to Chianti Region](https://expedia.ca/Cheap-Flights-To-Chianti-Region.d603148.Travel-Guide-Flights)[Things to do in Chianti Region](https://expedia.ca/Things-To-Do-In-Chianti-Region.d603148.Travel-Guide-Activities)[Chianti Region Car Rentals](https://expedia.ca/Car-Rentals-In-Chianti-Region.d603148.Car-Rental-Guide)[Chianti Region Vacation Packages](https://expedia.ca/Chianti-Region.d603148.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/410000/410487-Torre-Del-Mangia.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with Free Parking in Chianti Region ![](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 availability on Chianti Region Hotels with Free Parking Tonight [Oct 29 - Oct 30](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-10-29&endDate=2025-10-30&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 30 - Oct 31](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-10-30&endDate=2025-10-31&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-10-31&endDate=2025-11-02&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chianti Region Hotels with Free Parking ![Property grounds](https://images.trvl-media.com/lodging/5000000/4990000/4985100/4985032/d80b49b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room (Castello La Leccia)](https://images.trvl-media.com/lodging/5000000/4990000/4985100/4985032/600a5ff9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/5000000/4990000/4985100/4985032/f3280e61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily local cuisine breakfast](https://images.trvl-media.com/lodging/5000000/4990000/4985100/4985032/53b0db46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castello La Leccia Castellina in Chianti 10/10 Exceptional (90) "Very beautiful property. Staff is very welcoming and professional." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) haluk CA $270 CA $303 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Castello-La-Leccia.h4985032.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/27000000/26930000/26920200/26920147/93db43df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Romantic Double Room, 1 King Bed, Vineyard View | Bathroom](https://images.trvl-media.com/lodging/27000000/26930000/26920200/26920147/40281bf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch, dinner served; local and international cuisine, garden views ](https://images.trvl-media.com/lodging/27000000/26930000/26920200/26920147/805e5cad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room, Non Smoking](https://images.trvl-media.com/lodging/27000000/26930000/26920200/26920147/9c893ab5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tenuta CorteDomina Radda in Chianti 9.8/10 Exceptional (130) "It's a beautiful property, truly Tuscan style, clean, comfortable, and cozy. Great service, the staff is super friendly, helpful, and willing to assist with anything you need. They produce their own wine, which is delicious. The breakfast is varied and tasty." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ana CA $178 CA $203 total includes taxes & fees Nov 14 - Nov 15 [](https://www.expedia.ca/Radda-In-Chianti-Hotels-Tenuta-CorteDomina.h26920147.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/21000000/20490000/20484000/20483959/56ce48bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/21000000/20490000/20484000/20483959/826b9811.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/21000000/20490000/20484000/20483959/8e8d0a1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, minibar, in-room safe](https://images.trvl-media.com/lodging/21000000/20490000/20484000/20483959/7531f1d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Salvadonica - Borgo del Chianti San Casciano in Val di Pesa 9.6/10 Exceptional (252) "Beautiful setting with delicious food and attentive staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paula CA $151 CA $172 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Salvadonica.h20483959.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/43000000/42060000/42059900/42059842/aaf98c1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Room, located in a dependence, at 300 meters from the historic Villa, accessible with stairs](https://images.trvl-media.com/lodging/43000000/42060000/42059900/42059842/a4499de8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/43000000/42060000/42059900/42059842/079f0a96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/43000000/42060000/42059900/42059842/70e53beb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Torre a Cona Wine Estate Rignano sull'Arno 9.6/10 Exceptional (90) "Beautiful place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shariza CA $517 CA $572 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Rignano-SullArno-Hotels-Torre-A-Cona-Wine-Estate.h42059842.Hotel-Information) ![Poolside bar](https://images.trvl-media.com/lodging/2000000/1130000/1122100/1122097/72f1acd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Land view from property](https://images.trvl-media.com/lodging/2000000/1130000/1122100/1122097/31773bd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; pool views](https://images.trvl-media.com/lodging/2000000/1130000/1122100/1122097/2518e1c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1130000/1122100/1122097/bd9729ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relais Vignale & Spa Radda in Chianti 9.2/10 Wonderful (282) "Beautiful clean quiet. Would visit again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) jaycie CA $230 CA $303 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Radda-In-Chianti-Hotels-Relais-Vignale-Spa.h1122097.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/18000000/17970000/17963800/17963776/510521f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/18000000/17970000/17963800/17963776/a0449af2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite | Living area](https://images.trvl-media.com/lodging/18000000/17970000/17963800/17963776/4dfdaf4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/18000000/17970000/17963800/17963776/6c72b535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Borgo Del Cabreo Greve in Chianti 10/10 Exceptional (266) "Beautiful location, great staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey CA $290 CA $326 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Borgo-Del-Cabreo.h17963776.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/3167b59e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/da2e11e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/d55388f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa, 2 Bedrooms | Living area](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/7c35f9bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castello Vicchiomaggio Greve in Chianti 9.4/10 Exceptional (369) "Beautiful grounds. Room was spacious and the breakfast was delicious. Very friendly staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Devin CA $239 CA $263 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Castello-Vicchiomaggio.h7564854.Hotel-Information) ![Outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/3000000/2530000/2523800/2523750/d7de1ccd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/3000000/2530000/2523800/2523750/446df379.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/3000000/2530000/2523800/2523750/0e954f88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Tree House](https://images.trvl-media.com/lodging/3000000/2530000/2523800/2523750/f9e9d290.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa I Barronci Resort & Spa San Casciano in Val di Pesa 9.2/10 Wonderful (407) "Staff wa really accommodating. Resort really has it all to almost never had to leave they even helped us book a nice wine tour! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Luis CA $135 CA $158 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Villa-I-Barronci-Resort-Spa.h2523750.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/3000000/2550000/2540800/2540742/cac6885d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/3000000/2550000/2540800/2540742/49c8818d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/3000000/2550000/2540800/2540742/3abb8b31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Spa](https://images.trvl-media.com/lodging/3000000/2550000/2540800/2540742/e313c01a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Belvedere di San Leonino Castellina in Chianti 9.6/10 Exceptional (176) "Brilliant hotel , pool and restaurant " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Daniel CA $126 CA $148 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Belvedere-Di-San-Leonino.h2540742.Hotel-Information) ![Apartment, 2 Bedrooms](https://images.trvl-media.com/lodging/24000000/23190000/23183900/23183851/b54f0e1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Manicures and pedicures, massages](https://images.trvl-media.com/lodging/24000000/23190000/23183900/23183851/4f19efbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Terre di Baccio Greve in Chianti 10/10 Exceptional (68) "Very nice hotel , breakfast very good , is a winery and very good Chianti Is a big hotel All the staff is very kind I liked this hotel very much I recommend!!!!!!!" ![Mexico](https://a.travel-assets.com/egds/marks/flags/mx.svg) Orlando Santini CA $316 CA $354 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Terre-Di-Baccio.h23183851.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=2025-11-12&endDate=2025-11-13®ionId=603148&adults=2&amenities=FREE_PARKING&sort=RECOMMENDED&openPlayBack=true) ## Top Chianti Region Hotel Reviews ![Villa Castiglione](//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](//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) ![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 "Everything in this hotel was perfect from Super friendly and accomating staff, amazing food and bar area ! And my room was super comfortable and spacious.. defintley will come back!!! " [](https://expedia.ca/Barberino-Tavarnelle-Hotels-Hotel-Borgo-Di-Cortefreda-Relais.h1216478.Hotel-Information) ![Il Borro - Relais & Châteaux](//images.trvl-media.com/lodging/6000000/5590000/5585700/5585638/4a6bd899_y.jpg) ### Il Borro - Relais & Châteaux 10/10 Excellent "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) ![Park Hotel Chianti](//images.trvl-media.com/lodging/2000000/1410000/1402100/1402089/9fa8e1be_y.jpg) ### Park Hotel Chianti 10/10 Excellent "Lovely hotel in Chianti, staff were outstanding! " [](https://expedia.ca/Barberino-Tavarnelle-Hotels-Park-Hotel-Chianti.h1402089.Hotel-Information) ![Hotel Toscana Ambassador](//images.trvl-media.com/lodging/2000000/1430000/1429500/1429488/7717f75b_y.jpg) ### Hotel Toscana Ambassador 10/10 Excellent "Excellent emplacement pour explorer la région. Facile de se trouver un stationnement gratuit en face de l'hôtel. Chambre propre, mais relativement sans charme, plutôt impersonnelle côté déco, mais tout ce dont on a besoin y est toutefois, donc je recommande si vous cherchez qqchose d'efficace, abordable et fonctionnel. Le déjeuner buffet est très bon!" [](https://expedia.ca/Poggibonsi-Hotels-Hotel-Toscana-Ambassador.h1429488.Hotel-Information) ![Hotel Certaldo](//images.trvl-media.com/lodging/2000000/1680000/1675500/1675499/0f881b23_y.jpg) ### Hotel Certaldo 10/10 Excellent "Beautiful garden in the back" [](https://expedia.ca/Certaldo-Hotels-Hotel-Certaldo.h1675499.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 "Spa experience was wonderful!!" [](https://expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Villa-I-Barronci-Resort-Spa.h2523750.Hotel-Information) ![Palagina la Dimora](//images.trvl-media.com/lodging/2000000/1670000/1661500/1661496/2659699d_y.jpg) ### Palagina la Dimora 10/10 Excellent "Très bien situé pour une visite de Florence et de vignobles de Chianti. Excellent restaurant. Personnel très courtois et attentionné. Chambre spacieuse. Seul hic: la climatisation ne fonctionnait pas." 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