Title: 5 Stars Hotels in Chianti Region, Tuscany from CA $69 - Find Cheap Chianti Region Hotels With 5 Stars | 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) # 5 Stars Hotels in Chianti Region, Tuscany from CA $69 - ![](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 5 Star Hotels Tonight [Dec 9 - Dec 10](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-12-09&endDate=2025-12-10&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 10 - Dec 11](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-12-10&endDate=2025-12-11&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-12-12&endDate=2025-12-14&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-12-19&endDate=2025-12-21&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chianti Region 5-star 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) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/2000000/1280000/1279800/1279768/96aac713.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) ![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 $1,154 CA $1,283 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-COMO-Castello-Del-Nero.h1279768.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/3000000/2550000/2540800/2540741/75ac6194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/3000000/2550000/2540800/2540741/9f7c196f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Terrace](https://images.trvl-media.com/lodging/3000000/2550000/2540800/2540741/9893307b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2550000/2540800/2540741/78369923.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castello di Spaltenna- Small Luxury Hotels of the World Gaiole in Chianti 9.6/10 Exceptional (261) "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! " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Catherine [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Castello-Di-Spaltenna.h2540741.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/96000000/95120000/95114100/95114066/513e5451.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo | Living area](https://images.trvl-media.com/lodging/96000000/95120000/95114100/95114066/97151d85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Double Room](https://images.trvl-media.com/lodging/96000000/95120000/95114100/95114066/3c8dbeb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Room | Living area](https://images.trvl-media.com/lodging/96000000/95120000/95114100/95114066/dd719a4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pieve Aldina - Fontenille Collection Radda in Chianti 10/10 Exceptional (32) "Gorgeous design, high quality, delicious food and wine, friendly and helpful staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lara [](https://www.expedia.ca/Radda-In-Chianti-Hotels-Pieve-Aldina.h95114066.Hotel-Information) ![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/2000000/1190000/1180600/1180553/8d2f3252.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/2000000/1190000/1180600/1180553/cbf46611.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/2000000/1190000/1180600/1180553/068bc6ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1190000/1180600/1180553/89fdd299.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Borgo Vescine Radda in Chianti 9.4/10 Exceptional (244) "This was a beautiful location. The room was spacious and loved the patio for coffee in the mornings. It was very private. We enjoyed the pool and restaurants were great. Breakfast was amazing. We did the picnic and dinner in the Olive Garden and loved getting to know others at our table. The chefs food choices were so wonderful. We would definitely stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sherie [](https://www.expedia.ca/Radda-In-Chianti-Hotels-Il-Borgo-Di-Vescine.h1180553.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) ![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) ![Garden](https://images.trvl-media.com/lodging/17000000/16580000/16576000/16575993/2bac478f.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) ![](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%2F5Star-Chianti-Region-Hotels.s50-0-d603148.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Chianti-Region-Hotels.s50-0-d603148.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Chianti Region. ![Hotel Ristorante Alcide](https://images.trvl-media.com/lodging/2000000/1410000/1402100/1402058/d779a567_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hotel Ristorante Alcide Viale Marconi, 67/A Poggibonsi SI CA $62 CA $69 total Dec 14 - Dec 15 includes taxes & fees 8/10 Very Good! (460 reviews) [](https://expedia.ca/Poggibonsi-Hotels-Hotel-Ristorante-Alcide.h1402058.Hotel-Information) ![Hotel Borgo di Cortefreda Relais](https://images.trvl-media.com/lodging/2000000/1220000/1216500/1216478/288cff0c_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hotel Borgo di Cortefreda Relais Via Roma 191 Barberino Tavarnelle FI CA $121 CA $142 total Dec 12 - Dec 13 includes taxes & fees 9.4/10 Exceptional! (472 reviews) [](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?impolicy=resizecrop&rw=402&ra=fit) ### Hotel Toscana Ambassador Via Salceto, 11 Poggibonsi SI CA $95 CA $105 total Jan 5 - Jan 6, 2026 includes taxes & fees 8/10 Very Good! (306 reviews) [](https://expedia.ca/Poggibonsi-Hotels-Hotel-Toscana-Ambassador.h1429488.Hotel-Information) Still don't see what you're looking for? [See all properties in Chianti Region.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=10%2F12%2F2025&endDate=11%2F12%2F2025®ionId=603148&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=10%2F12%2F2025&endDate=11%2F12%2F2025®ionId=603148&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=10%2F12%2F2025&endDate=11%2F12%2F2025®ionId=603148&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=10%2F12%2F2025&endDate=11%2F12%2F2025®ionId=603148&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=10%2F12%2F2025&endDate=11%2F12%2F2025®ionId=603148&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=10%2F12%2F2025&endDate=11%2F12%2F2025®ionId=603148&star=50&star=50&amenities=WATER_PARK) 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. ## Learn more about Chianti Region Take a sightseeing trip of Tuscany's renowned wine region and visit its vineyards, wineries, ancient churches, castles and hilltop villages. [See all hotels in Chianti Region](https://www.expedia.ca/Hotel-Search?startDate=2025-12-23&endDate=2025-12-24&adults=2®ionId=603148) ![Chianti Region showing farmland](https://images.trvl-media.com/place/603148/a6b4be95-df3f-44a2-bf6d-bb1e6f500def.jpg?impolicy=fcrop&w=900&h=506&p=1&q=high) ## Top Chianti Region Hotel Reviews ![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) ![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) ## Find out more about Chianti Region ## Five Star Hotels in Chianti Region There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Chianti Region so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Chianti Region and get ready to be pampered like never before. #### Get a Great Deal on 5-Star Hotels in Chianti Region Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places. Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town. #### Make Your Escape to Chianti Region The results are in, and Chianti Region 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Chianti Region! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Chianti Region today and settle down in the lap of luxury tomorrow. ## Frequently asked questions ### How much does it cost to stay in a 5-star hotel in Chianti Region? > - Search for the lowest price per night from CA $69 ### What makes a hotel 5 stars in Chianti Region? ### Are there any 5-star all-inclusive resorts in Chianti Region? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [3 Star Hotels in Arezzo ](https://www.expedia.ca/3Star-Arezzo-Hotels.s30-0-d11306.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Florence ](https://www.expedia.ca/3Star-Florence-Hotels.s30-0-d1222.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Montagna Fiorentina ](https://www.expedia.ca/3Star-Montagna-Fiorentina-Hotels.s30-0-d6131290.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Siena ](https://www.expedia.ca/3Star-Siena-Hotels.s30-0-d9821.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Arezzo ](https://www.expedia.ca/4Star-Arezzo-Hotels.s40-0-d11306.Travel-Guide-Filter-Hotels) - 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