Title: Book the Best Chianti Region Hotels with FREE PARKING in 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)[Vacation Rentals in Chianti Region](https://expedia.ca/Chianti-Region-Vacation-Rentals.d603148.Travel-Guide-VacationRentals)[Flights to Chianti Region](https://expedia.ca/Cheap-Flights-To-Chianti-Region.d603148.Travel-Guide-Flights)[Things to do in Chianti Region](https://expedia.ca/Things-To-Do-In-Chianti-Region.d603148.Travel-Guide-Activities)[Chianti Region Car Rentals](https://expedia.ca/Car-Rentals-In-Chianti-Region.d603148.Car-Rental-Guide)[Chianti Region Vacation Packages](https://expedia.ca/Chianti-Region.d603148.Destination-Travel-Guides) ![Chianti Region showing farmland](https://images.trvl-media.com/place/603148/a6b4be95-df3f-44a2-bf6d-bb1e6f500def.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/603148/a6b4be95-df3f-44a2-bf6d-bb1e6f500def.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Chianti Region Hotels with Free Parking Tonight [Jan 20 - Jan 21](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-01-20&endDate=2026-01-21&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 21 - Jan 22](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-01-21&endDate=2026-01-22&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-01-23&endDate=2026-01-25&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-01-30&endDate=2026-02-01&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chianti Region hotels with parking ![Exterior](https://images.trvl-media.com/lodging/11000000/10510000/10507800/10507728/35ef77e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Regional cuisine](https://images.trvl-media.com/lodging/11000000/10510000/10507800/10507728/b32279fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/11000000/10510000/10507800/10507728/f71cac1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/11000000/10510000/10507800/10507728/ee3f2b2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Art Hotel Villa Agape [](https://www.expedia.ca/Florence-Hotels-Art-Hotel-Villa-Agape.h10507728.Hotel-Information) Oltrarno 9.8/10 Exceptional (1,001 reviews) "Exceptional hospitality from the entire team. We truly had a wonderful stay. Breakfast was perfect, and the hotel’s location and peaceful, relaxing atmosphere make you want to stay on the property and not leave." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edgar CA $204 CA $246 total includes taxes & fees Feb 17 - Feb 18 [](https://www.expedia.ca/Florence-Hotels-Art-Hotel-Villa-Agape.h10507728.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/21000000/20490000/20484000/20483959/4eac4992.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/21000000/20490000/20484000/20483959/56ce48bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 8 AM to 8:30 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/21000000/20490000/20484000/20483959/47d0a085.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/21000000/20490000/20484000/20483959/4d9792cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Salvadonica - Borgo del Chianti [](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Salvadonica.h20483959.Hotel-Information) San Casciano in Val di Pesa 9.6/10 Exceptional (265 reviews) "One of the finest boutique hotels I have ever stayed in. The hosts, the view, the room, the food they serve, the location is all memorable. The stay was the highlight of our trip to Florence ." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $144 CA $165 total includes taxes & fees Feb 17 - Feb 18 [](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Salvadonica.h20483959.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/90000000/89040000/89035100/89035039/72f32f77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sauna, hot tub](https://images.trvl-media.com/lodging/90000000/89040000/89035100/89035039/20d8f620.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sauna, hot tub](https://images.trvl-media.com/lodging/90000000/89040000/89035100/89035039/7789bc21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served, Italian cuisine](https://images.trvl-media.com/lodging/90000000/89040000/89035100/89035039/7ff42156.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### IQ Hotel Firenze [](https://www.expedia.ca/Florence-Hotels-IQ-Hotel-Firenze.h89035039.Hotel-Information) Historic Centre of Florence 9.6/10 Exceptional (1,122 reviews) "The hotel was very well equipped. Great location so easy to walk everywhere. Staff were super helpful!" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Natalie CA $131 CA $166 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Florence-Hotels-IQ-Hotel-Firenze.h89035039.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) ![Steam room, Turkish bath, body scrubs, massages](https://images.trvl-media.com/lodging/2000000/1140000/1131000/1130942/e763d814.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) ![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) ### 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 $182 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Loro-Ciuffenna-Hotels-Villa-Cassia-Di-Baccano.h1130942.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/1000000/850000/849900/849839/24f89230.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/1000000/850000/849900/849839/c2f57f8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/850000/849900/849839/b6548f53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/850000/849900/849839/7a86f801.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Orto De Medici Hotel [](https://www.expedia.ca/Florence-Hotels-Orto-De-Medici-Hotel.h849839.Hotel-Information) Historic Centre of Florence 9.6/10 Exceptional (1,001 reviews) "Excellent place to stay in Florence!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Miryam CA $181 CA $221 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Florence-Hotels-Orto-De-Medici-Hotel.h849839.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/8a9d9969.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; Italian cuisine, alfresco dining ](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/a55956cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/d6652f62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/74216348.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Certosa di Pontignano [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-La-Certosa-Di-Pontignano.h9797642.Hotel-Information) Castelnuovo Berardenga 9.6/10 Exceptional (508 reviews) "Excellent place to stay even for the next time. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Xuejie CA $151 CA $172 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-La-Certosa-Di-Pontignano.h9797642.Hotel-Information) ![Seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/3000000/2540000/2537900/2537801/089cca52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2540000/2537900/2537801/f5b61d12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Winery](https://images.trvl-media.com/lodging/3000000/2540000/2537900/2537801/cbeec78c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch and dinner served, alfresco dining ](https://images.trvl-media.com/lodging/3000000/2540000/2537900/2537801/afca094e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castello di Meleto [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Castello-Di-Meleto.h2537801.Hotel-Information) Gaiole in Chianti 8.8/10 Excellent (93 reviews) "We had a great time" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anna CA $207 CA $241 total includes taxes & fees Feb 19 - Feb 20 [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Castello-Di-Meleto.h2537801.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1220000/1216500/1216478/18221048.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples treatment rooms, sauna, steam room, Turkish bath](https://images.trvl-media.com/lodging/2000000/1220000/1216500/1216478/3d30ae6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; local cuisine, garden views ](https://images.trvl-media.com/lodging/2000000/1220000/1216500/1216478/cf05a6fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1220000/1216500/1216478/56435536.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Borgo di Cortefreda Relais [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Hotel-Borgo-Di-Cortefreda-Relais.h1216478.Hotel-Information) Barberino Tavarnelle 9.4/10 Exceptional (483 reviews) "The views were spectacular and the grounds were so peaceful" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle CA $123 CA $145 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Hotel-Borgo-Di-Cortefreda-Relais.h1216478.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) ![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) ![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) ### 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 (98 reviews) "Great people, great location great service" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) James CA $185 CA $211 total includes taxes & fees Feb 20 - Feb 21 [](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Villa-Il-Fedino.h2723529.Hotel-Information) ![Indoor pool, seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1290000/1289200/1289163/187ae210.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1290000/1289200/1289163/637c56f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/2000000/1290000/1289200/1289163/37d88bc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1290000/1289200/1289163/7c981965.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Palazzo San niccolò & Spa [](https://www.expedia.ca/Radda-In-Chianti-Hotels-Hotel-Palazzo-San-Niccolo.h1289163.Hotel-Information) Radda in Chianti 9.2/10 Wonderful (179 reviews) "Ideal country setting" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Dee CA $147 CA $171 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Radda-In-Chianti-Hotels-Hotel-Palazzo-San-Niccolo.h1289163.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=2026-02-03&endDate=2026-02-04®ionId=603148&adults=2&amenities=FREE_PARKING&sort=RECOMMENDED&openPlayBack=true) ## 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 Lorenzo & SPA](https://images.trvl-media.com/lodging/4000000/3480000/3475000/3474921/1af45070_y.jpg) ### Hotel Palazzo San Lorenzo & SPA 10/10 Excellent "Livia was amazing and made me feel very welcomed. She has great customer service skills and showed me where places were on the map. The room and bathroom was spacious." [](https://expedia.ca/Colle-Di-Val-DElsa-Hotels-Hotel-Palazzo-San-Lorenzo-SPA.h3474921.Hotel-Information) ![Villa San Lucchese](https://images.trvl-media.com/lodging/2000000/1690000/1685900/1685892/f05836b4_y.jpg) ### Villa San Lucchese 10/10 Excellent "Beautiful place Great service " [](https://expedia.ca/Poggibonsi-Hotels-Villa-San-Lucchese.h1685892.Hotel-Information) ![Castello di Fonterutoli Wine Resort](https://images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/9f05cf5a_y.jpg) ### Castello di Fonterutoli Wine Resort 10/10 Excellent "Very clean,staff was very kind and helpful. Looking forward to come back! 😊" [](https://expedia.ca/Castellina-In-Chianti-Hotels-Castello-Di-Fonterutoli.h5172395.Hotel-Information) ![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) ![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) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - [Lgbt Friendly Hotels in Antella ](https://www.expedia.ca/Antella-Hotels-LGBT-Friendly-Hotel.0-0-d6142059-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Badia Coltibuono Hotels ](https://www.expedia.ca/Badia-Coltibuono-Hotels.d553248635975857717.Travel-Guide-Hotels) - [Casole Hotels ](https://www.expedia.ca/Casole-Hotels.d3000429476.Travel-Guide-Hotels) - [B&B in Castellina in Chianti ](https://www.expedia.ca/Castellina-In-Chianti-Bed-And-Breakfast.d55534-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Luxury Hotels in Castellina in Chianti ](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Luxury-Hotel.0-0-d55534-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Hotel Wedding Venues Hotels in Castellina in Chianti ](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Wedding-Hotels.0-0-d55534-tWeddingHotels.Travel-Guide-Filter-Hotels) - 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