Title: Chianti Region Castles from CA $133 | 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 prices for these dates Next weekend [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-04-03&endDate=2026-04-05&adults=2&lodging=CASTLE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-04-10&endDate=2026-04-12&adults=2&lodging=CASTLE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-04-24&endDate=2026-04-26&adults=2&lodging=CASTLE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-05-22&endDate=2026-05-24&adults=2&lodging=CASTLE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chianti Region castles ![Aerial view](https://images.trvl-media.com/lodging/115000000/114730000/114728600/114728523/50689ae3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/115000000/114730000/114728600/114728523/cc1d13c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/115000000/114730000/114728600/114728523/c4d4cf02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/115000000/114730000/114728600/114728523/16de4c6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castello Di Montemasso [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Castello-Di-Montemasso.h114728523.Hotel-Information) Greve in Chianti 9.8/10 Exceptional (13 reviews) "Sanja and her husband were amazing hosts. They made sure we had everything we needed. The place was so beautiful and comfortable. We loved it!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen CA $165 CA $184 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Castello-Di-Montemasso.h114728523.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/105000000/104780000/104774800/104774707/b1eba8b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/105000000/104780000/104774800/104774707/18ff7255.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/105000000/104780000/104774800/104774707/e6c8855b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/105000000/104780000/104774800/104774707/e1152786.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Torre Sassa - Torre Medievale in Toscana [](https://www.expedia.ca/Montecatini-Val-Di-Cecina-Hotels-Torre-Sassa-Torre-Medievale-In-Toscana.h104774707.Hotel-Information) Sassa 10/10 Exceptional (1 review) "This tower was absolutely beautiful, spacious and clean. The medieval decor was awesome. Stefania came in to cook and it was absolutely amazing and delicious. We left some items behind and Giacomo contacted us promptly and is shipping the items back home to us. An absolutely wonderful experience!!" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Cindylou CA $715 CA $1,003 total includes taxes & fees Mar 27 - Mar 28 [](https://www.expedia.ca/Montecatini-Val-Di-Cecina-Hotels-Torre-Sassa-Torre-Medievale-In-Toscana.h104774707.Hotel-Information) ![Standard Triple Room](https://images.trvl-media.com/lodging/108000000/107200000/107195900/107195877/8df84232.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/108000000/107200000/107195900/107195877/51882a03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107200000/107195900/107195877/0390d01b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107200000/107195900/107195877/108d1b99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cattaleya Rooms [](https://www.expedia.ca/Florence-Hotels-HOSTEL-SANTA-MARIA-NOVELLA.h107195877.Hotel-Information) Santa Maria Novella 8.4/10 Very good (38 reviews) "Had a 2 night stayover in Firenze, and thanks to the good location, we only had a small walk to the city centre. Great value for parking at the Apcoa underground park, 10€ for 24h!! " ![Germany](https://a.travel-assets.com/egds/marks/flags/de.svg) Metin CA $103 CA $133 total includes taxes & fees Mar 25 - Mar 26 [](https://www.expedia.ca/Florence-Hotels-HOSTEL-SANTA-MARIA-NOVELLA.h107195877.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106750000/106742900/106742853/1b39f7ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/107000000/106750000/106742900/106742853/0097a72c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106750000/106742900/106742853/90dd5231.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/107000000/106750000/106742900/106742853/c27e2fe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Montelifré Castle [](https://www.expedia.ca/Montalcino-Hotels-Monte-Lifre-Castle.h106742853.Hotel-Information) Montalcino CA $937 CA $1,298 total includes taxes & fees Apr 17 - Apr 18 [](https://www.expedia.ca/Montalcino-Hotels-Monte-Lifre-Castle.h106742853.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/40000000/39140000/39138500/39138427/a75024ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/40000000/39140000/39138500/39138427/da8ac4b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/40000000/39140000/39138500/39138427/d30c34da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/40000000/39140000/39138500/39138427/14ab515a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### CASTELLO NELLE CRETE [](https://www.expedia.ca/Asciano-Hotels-CASTELLO-NELLE-CRETE.h39138427.Hotel-Information) Siena 10/10 Exceptional (1 review) "Picture yourself in a century-old castle high on a hill in the heart of Tuscany. Your surroundings are those of a majestic Monet painting. Birds humming, and the smell of fresh croissants fills the air. A cup of hot cappucino is being brought to you by the most professional but always smiling and always friendly staff .No you're not dreaming, you and your family of 30 are guests at Villa Leonina, Every room has an ensuite bathroom with daily maintenance and fresh towels. The kitchen and... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) joanne s. CA $24,359 CA $24,359 total includes taxes & fees Mar 25 - Mar 26 [](https://www.expedia.ca/Asciano-Hotels-CASTELLO-NELLE-CRETE.h39138427.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=2026-04-07&endDate=2026-04-08®ionId=603148&adults=2&lodging=CASTLE&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-Castles.d603148-aaCastles.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChianti-Region-Castles.d603148-aaCastles.Travel-Guide-Accommodation) ## Top Chianti Region Hotel Reviews ![Castello di Fonterutoli Wine Resort](https://images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/f80bb145_y.jpg) ### Castello di Fonterutoli Wine Resort 10/10 Excellent "Le personnel est super accueillant. L’endroit est paradisiaque, la bouffe est excellente et le vin divin." [](https://expedia.ca/Castellina-In-Chianti-Hotels-Castello-Di-Fonterutoli.h5172395.Hotel-Information) ![Castello Vicchiomaggio](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/62d09fdf_y.jpg) ### Castello Vicchiomaggio 10/10 Excellent "One of the most amazing experiences we've ever had. I recommend this place 100%. The castle is beautiful, the service is amazing, the suites are beautiful, and the wine tour with lunch is fantastic. " [](https://expedia.ca/Greve-In-Chianti-Hotels-Castello-Vicchiomaggio.h7564854.Hotel-Information) ![Borgo Del Cabreo](https://images.trvl-media.com/lodging/18000000/17970000/17963800/17963776/6c72b535_y.jpg) ### Borgo Del Cabreo 10/10 Excellent "Borgo del Cabreo was our favorite place we stayed on our trip to Italy in March. Every detail of the Borgo was thoughtfully curated and is situated in the most beautiful setting in the Chianti region. The rooms and bathrooms were big. The king size bed was very comfortable. The breakfast was delicious in the most idyllic setting. The city center of Florence was loud at night even in March, so coming here was very restorative to my soul. The sounds of nature, birds singing, the idyllic scenary, was a wonderful contrast to Florence. We had the most wonderful dinner and wine at their sister property Pietra del Cabreo. My kids and I would return to Italy just to stay here again. " [](https://expedia.ca/Greve-In-Chianti-Hotels-Borgo-Del-Cabreo.h17963776.Hotel-Information) ![Villa I Barronci Resort & Spa](https://images.trvl-media.com/lodging/3000000/2530000/2523800/2523750/57a598f5_y.jpg) ### Villa I Barronci Resort & Spa 10/10 Excellent "Wonderful stay. Clean rooms. Such friendly and accommodating staff. The restaurant was temporarily closed but they still made sure there was a full breakfast buffet every morning and dinner had a set menu option each night. The pool was open and warm! Lots of parking if you’re renting a car. Great proximity to Florence and rest of Tuscany if you plan to tour around yourself. " [](https://expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Villa-I-Barronci-Resort-Spa.h2523750.Hotel-Information) ![Salvadonica - Borgo del Chianti](https://images.trvl-media.com/lodging/21000000/20490000/20484000/20483959/4eac4992_y.jpg) ### Salvadonica - Borgo del Chianti 10/10 Excellent "We loved our time at Salvadonica. The food was excellent and we particularly enjoyed the cooking class. I would love to go back during grape and olive harvesting season. The staff was friendly and very helpful " [](https://expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Salvadonica.h20483959.Hotel-Information) ![Villa Casagrande Resort & SPA](https://images.trvl-media.com/lodging/1000000/900000/891700/891661/994bfd62_y.jpg) ### Villa Casagrande Resort & SPA 10/10 Excellent "The staff was extremely knowledgeable, friendly, and available when we had questions. The room was clean and the bed was comfortable. The property was also well maintained and beautiful." [](https://expedia.ca/Figline-E-Incisa-Valdarno-Hotels-Villa-Casagrande-Resort-SPA.h891661.Hotel-Information) ![hu Firenze Certosa camping in town](https://images.trvl-media.com/lodging/102000000/101510000/101503700/101503652/dad23b8c_y.jpg) ### hu Firenze Certosa camping in town 10/10 Excellent "Fantastic! The staff was very helpfull, the rooms were impeacable (and warm) and the dinner at the restaurant was delicious. Better than an hotel in our opinion. Congrats! The only drawback as lack of EV charger... but they said it was coming.." [](https://expedia.ca/Impruneta-Hotels-Firenze-Certosa-Camping.h101503652.Hotel-Information) ![Hotel Toscana Ambassador](https://images.trvl-media.com/lodging/2000000/1430000/1429500/1429488/2f9ea910_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) ![Agriturismo San Sano](https://images.trvl-media.com/lodging/2000000/1500000/1492000/1491964/6322c664_y.jpg) ### Agriturismo San Sano 10/10 Excellent "You can never go wrong in Toscana , even in off season . San Sano even more so, hidden from mass tourism. " [](https://expedia.ca/Gaiole-In-Chianti-Hotels-Hotel-Residence-San-Sano.h1491964.Hotel-Information) ## Find out more about Chianti Region ## Chianti Region Castles information | Number of reviews | 53 | | ----------------- | ---------- | | Accommodation | 48 Castles | | Lowest Price | CA $133 | | Highest Price | CA $24,359 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [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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