Title: Book the Best Chianti Region LUXURY Hotels - Upscale Hotels in Chianti Region | 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) # Find luxury hotels 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 Luxury Hotels Tonight [Dec 1 - Dec 2](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-12-01&endDate=2025-12-02&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Dec 2 - Dec 3](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-12-02&endDate=2025-12-03&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) This weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-12-05&endDate=2025-12-07&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-12-12&endDate=2025-12-14&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Top Chianti Region Luxury Hotels ![2 restaurants, breakfast, lunch, dinner served; international cuisine](https://images.trvl-media.com/lodging/2000000/1280000/1279800/1279768/5908bcb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Heritage)](https://images.trvl-media.com/lodging/2000000/1280000/1279800/1279768/48bd2186.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/2000000/1280000/1279800/1279768/7f490258.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1280000/1279800/1279768/69679e88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### COMO Castello Del Nero Barberino Tavarnelle 9.6/10 Exceptional (132) "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). " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew CA $1,163 CA $1,293 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-COMO-Castello-Del-Nero.h1279768.Hotel-Information) ![Couples treatment rooms, Turkish bath, body treatments, body wraps](https://images.trvl-media.com/lodging/3000000/2590000/2589400/2589383/b16ad5c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/3000000/2590000/2589400/2589383/e302ad8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, lunch, dinner served; Italian cuisine](https://images.trvl-media.com/lodging/3000000/2590000/2589400/2589383/f854e266.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, minibar, in-room safe, individually decorated](https://images.trvl-media.com/lodging/3000000/2590000/2589400/2589383/9db7bc16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castel Monastero - The Leading Hotels of the World Castelnuovo Berardenga 8.8/10 Excellent (144) "Had two wonderful nights at the Castel Monastero (wish we had more). Will definitely go back" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) John CA $787 CA $882 total includes taxes & fees Dec 20 - Dec 21 [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-Castel-Monastero.h2589383.Hotel-Information) ![Ballroom](https://images.trvl-media.com/lodging/1000000/800000/796700/796662/8b42326b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/1000000/800000/796700/796662/02562aa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, Terrace | View from room](https://images.trvl-media.com/lodging/1000000/800000/796700/796662/239d33c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/800000/796700/796662/4fe0a1f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Grand Hotel Continental Siena – Starhotels Collezione Siena City Centre 9.2/10 Wonderful (573) "Great hotel / room, city center, friendly staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nebojsa CA $299 CA $339 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Siena-Hotels-Grand-Hotel-Continental-Siena-Starhotels-Collezione.h796662.Hotel-Information) ![2 restaurants, lunch, dinner served; local cuisine](https://images.trvl-media.com/lodging/1000000/530000/528500/528471/61bcbebb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite Loggia | Garden](https://images.trvl-media.com/lodging/1000000/530000/528500/528471/d88fe9ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, free cabanas, pool umbrellas](https://images.trvl-media.com/lodging/1000000/530000/528500/528471/739b27a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/530000/528500/528471/ca53ff62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Borgo San Felice Resort Castelnuovo Berardenga 9.8/10 Exceptional (79) "One of our favorite places we’ve ever stayed at. 100% recommend. Hopefully we can visit again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria D [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-Hotel-Borgo-San-Felice.h528471.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1620000/1614900/1614881/4e848a61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite, Terrace (double)](https://images.trvl-media.com/lodging/2000000/1620000/1614900/1614881/8f6a8f66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1620000/1614900/1614881/7bd8c16b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1620000/1614900/1614881/e4c8730b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Le Fontanelle Castelnuovo Berardenga 9.8/10 Exceptional (95) "We had a perfect stay at this hotel! 100% recommend. " ![Netherlands](https://a.travel-assets.com/egds/marks/flags/nl.svg) Andreea [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-Hotel-Le-Fontanelle.h1614881.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/7000000/6110000/6102000/6101998/w4251h2830x3y0-76c9709c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor banquet area](https://images.trvl-media.com/lodging/7000000/6110000/6102000/6101998/bf5cff6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/7000000/6110000/6102000/6101998/9b837927.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/7000000/6110000/6102000/6101998/eec098ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relais la Costa - Dimora Storica Monteriggioni 9.6/10 Exceptional (73) "This place is wonderful, relaxing, and the staff was very helpful! It is a delightful stop on your tour through tuscany!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Samantha [](https://www.expedia.ca/Monteriggioni-Hotels-Relais-La-Costa-Dimora-Storica.h6101998.Hotel-Information) ![Poolside bar](https://images.trvl-media.com/lodging/3000000/2540000/2535700/2535673/0bc534ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/3000000/2540000/2535700/2535673/3dfcd37d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Memory foam beds, minibar, in-room safe, desk](https://images.trvl-media.com/lodging/3000000/2540000/2535700/2535673/5a530872.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/3000000/2540000/2535700/2535673/beb7cd7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa il Sasso - Dimora d'epoca Bagno a Ripoli 10/10 Exceptional (53) "Great place to stay near Florence. Very near and convenient if you need to be in Grassina. Good transportation by bus to Florence, but is ideal if you have a car to move around the beautiful Tuscany region. Breakfast is very good, and the staff couldn't be better hosts. Comfortable and clean rooms." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ALBERTO [](https://www.expedia.ca/Bagno-A-Ripoli-Hotels-Villa-Il-Sasso-Dimora-Depoca.h2535673.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) ![Tree House | View from room](https://images.trvl-media.com/lodging/3000000/2530000/2523800/2523750/5794994c.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) ### Villa I Barronci Resort & Spa San Casciano in Val di Pesa 9.2/10 Wonderful (411) "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 [](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Villa-I-Barronci-Resort-Spa.h2523750.Hotel-Information) ![3 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/17000000/16580000/16576000/16575993/a85d6e83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/17000000/16580000/16576000/16575993/2bac478f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch and dinner served, local and international cuisine](https://images.trvl-media.com/lodging/17000000/16580000/16576000/16575993/a31477a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite](https://images.trvl-media.com/lodging/17000000/16580000/16576000/16575993/f28fb58e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Le Calvane Montespertoli 9.6/10 Exceptional (82) "We had a wonderful time! The pool is amazing with an incredible view. The staff went out of their way to make our stay fantastic, especially our server Leonardo. The breakfast was great with eggs to order and everything freshly prepared. Highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephanie [](https://www.expedia.ca/Montespertoli-Hotels-Villa-Le-Calvane.h16575993.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/4000000/3560000/3556600/3556560/ac9c98a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive Double Room, Patio | View from room](https://images.trvl-media.com/lodging/4000000/3560000/3556600/3556560/20f4cb97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/4000000/3560000/3556600/3556560/e4212b2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/4000000/3560000/3556600/3556560/e1345488.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Locanda le Piazze Castellina in Chianti 9.8/10 Exceptional (183) "Absolutely gorgeous property!" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) David [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Locanda-Le-Piazze.h3556560.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=2025-12-15&endDate=2025-12-16®ionId=603148&adults=2&star=50&sort=RECOMMENDED&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=AFFINITY_BF_PROMO_603148) ## Top Chianti Region Hotel Reviews ![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) ![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) ![Relais Vignale & Spa](https://images.trvl-media.com/lodging/2000000/1130000/1122100/1122097/72f1acd5_y.jpg) ### Relais Vignale & Spa 10/10 Excellent "great place and great views. breakfast was very good." [](https://expedia.ca/Radda-In-Chianti-Hotels-Relais-Vignale-Spa.h1122097.Hotel-Information) ![Castello di Spaltenna- Small Luxury Hotels of the World](https://images.trvl-media.com/lodging/3000000/2550000/2540800/2540741/75ac6194_y.jpg) ### Castello di Spaltenna- Small Luxury Hotels of the World 10/10 Excellent "The breakfast was fresh with lots of options and a outdoor setting on the property. The property is beautiful, pool area and spa so peaceful. Excellent service in all areas of hotel! " [](https://expedia.ca/Gaiole-In-Chianti-Hotels-Castello-Di-Spaltenna.h2540741.Hotel-Information) ![Palazzo Leopoldo Dimora Storica & Spa](https://images.trvl-media.com/lodging/1000000/920000/911700/911656/95292913_y.jpg) ### Palazzo Leopoldo Dimora Storica & Spa 10/10 Excellent "Excellent breakfast. " [](https://expedia.ca/Radda-In-Chianti-Hotels-Palazzo-Leopoldo-Dimora-Storica-Spa.h911656.Hotel-Information) ![Villa Casagrande Resort & SPA](https://images.trvl-media.com/lodging/1000000/900000/891700/891661/f41faf16_y.jpg) ### Villa Casagrande Resort & SPA 10/10 Excellent "We had a great stay and loved the 2 bedrooms as a family of 4. Very friendly and accommodating staff" [](https://expedia.ca/Figline-E-Incisa-Valdarno-Hotels-Villa-Casagrande-Resort-SPA.h891661.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [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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