Title: Book the Best HISTORIC Hotels in Chianti Region 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 Historic 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 Historic Hotels Tonight [Oct 26 - Oct 27](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-10-26&endDate=2025-10-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 27 - Oct 28](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-10-27&endDate=2025-10-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chianti Region Historic Hotels ![Poolside bar](https://images.trvl-media.com/lodging/2000000/1130000/1122100/1122097/72f1acd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Manor House Balcony Suite | View from room](https://images.trvl-media.com/lodging/2000000/1130000/1122100/1122097/dd8f4786.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) ![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) ### 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 $231 CA $304 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Radda-In-Chianti-Hotels-Relais-Vignale-Spa.h1122097.Hotel-Information) ![Indoor pool, outdoor pool, open 8:30 AM to 7 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/870000/862800/862712/64683028.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/1000000/870000/862800/862712/5400ca9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/870000/862800/862712/8a343c92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/870000/862800/862712/f68e355f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Lecchi Hotel Wellness Poggibonsi 9.4/10 Exceptional (80) "My wife and I spent three nights at this hotel. We enjoyed the facilities- both in the spa and the surrounding areas. The staff are outstanding and take a real pride in ensuring that all our needs are taken care of. Food was excellent and service could not be faulted. Highly recommended." ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) ian CA $372 CA $419 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Poggibonsi-Hotels-Villa-Lecchi-Hotel-Wellness.h862712.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/3000000/2550000/2542300/2542211/bd706898.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/3000000/2550000/2542300/2542211/19526edb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/3000000/2550000/2542300/2542211/6d3bc507.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/3000000/2550000/2542300/2542211/9a894adc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Le Barone Greve in Chianti 9.6/10 Exceptional (138) "This was a beautiful property. The staff were very helpful and friendly. I would definitely recommend." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christie CA $334 CA $377 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Villa-Le-Barone.h2542211.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/36000000/35080000/35073400/35073320/4d3d05a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/36000000/35080000/35073400/35073320/913837e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/36000000/35080000/35073400/35073320/d22eee29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/36000000/35080000/35073400/35073320/128ac496.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK Ruffoli 9.4/10 Exceptional (20) "This is truly a unique and special property providing incredible value . One of the most beautiful views in a spectacular setting hidden away in the Tuscan hills above Panzano. A perfect location for day trips to vinyards, restaurants and the Chianti area. Our apartment was extremely well appointed and beautifully decorated. Spacious and varied outdoor sitting areas and patios with a very nice pool area. Our hostess Babette was extremely accomodating and informative which added to our overall... ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) James CA $138 CA $270 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Greve-In-Chianti-Hotels-UNIQUE-LARGE-TERRACE-WITH-VIEWS-TO-CHAINTI-VALLEY-AND-DRINK.h35073320.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/31000000/30370000/30366000/30365985/03b7a756.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, stereo](https://images.trvl-media.com/lodging/31000000/30370000/30366000/30365985/8ab29b22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/31000000/30370000/30366000/30365985/57b83369.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/31000000/30370000/30366000/30365985/717f0916.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### CHIANTI VINEYARDS OLIVE GROVES FOOD TASTINGS SCENIC VIEWS Ruffoli 9.2/10 Wonderful (28) "We loved the property - the kitchen and it's facilities was outstanding, same with the bathroom and the bedrooms. The exterior is peaceful and tranquil with some wonderful views. All in all a wonderful place to stay - highly recommended." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lorna M. CA $205 CA $439 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Greve-In-Chianti-Hotels-CHIANTI-VINEYARDS-OLIVE-GROVES-FOOD-TASTINGS-SCENIC-VIEWS.h30365985.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/68000000/67580000/67574900/67574832/7a5a0942.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, video library, stereo](https://images.trvl-media.com/lodging/68000000/67580000/67574900/67574832/942be153.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/68000000/67580000/67574900/67574832/55711d7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/68000000/67580000/67574900/67574832/3f750956.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Old medieval apartment San Donato 9.8/10 Exceptional (6) "It was a cute and spacious apartment in an medieval looking building. The owner (Leonardo) was a very receptive and pleasant person." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Ali CA $161 CA $197 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Old-Medieval-Apartment.h67574832.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39140000/39138700/39138677/b2996c58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/40000000/39140000/39138700/39138677/bdafe746.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/40000000/39140000/39138700/39138677/9753ec4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/40000000/39140000/39138700/39138677/7983115c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cennano Suite - enter apartment Montevarchi 10/10 Exceptional (3) "After and before the tourist rushes of Florence. I enjoyed a few very quiet and relaxing days in a beautiful and spacious place. " ![Germany](https://a.travel-assets.com/egds/marks/flags/de.svg) Judith T. CA $90 CA $184 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Montevarchi-Hotels-Cennano-Suite-Enter-Apartment.h39138677.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/35000000/34110000/34102500/34102457/2af46e59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34110000/34102500/34102457/935aaa7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34110000/34102500/34102457/a6f6a8e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34110000/34102500/34102457/e756d866.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Deluxe Room Nero su Bianco with A/C and Private Bathroom in Villa le Facezie B&B Terranuova Bracciolini 10/10 Exceptional (1) "Our short stay could not have been better. After difficulty with our phones and GPS, we arrived to a very gracious Christina and a relaxing stay. The breakfasts we're outstanding. Thank you so much, Christina." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lynn P. CA $224 CA $229 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Terranuova-Bracciolini-Hotels-Deluxe-Room-Nero-Su-Bianco-With-AC-And-Private-Bathroom-In-Villa-Le-Facezie-BB.h34102457.Hotel-Information) ![2 bedrooms, internet, bed sheets](https://images.trvl-media.com/lodging/40000000/39990000/39983400/39983368/34638ab1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/40000000/39990000/39983400/39983368/6e6f272f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39990000/39983400/39983368/6671f978.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/40000000/39990000/39983400/39983368/acc5b1eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wonderful Tuscan farmhouse with large spaces and panoramic views impruneta 9.8/10 Exceptional (24) "Loved the property and views,the owner was very helpful and informative would definitely come back" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andy P. CA $122 CA $392 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Impruneta-Hotels-Beautiful-Tuscan-Farmhouse-With-Large-Spaces-And-Panoramic-Views.h39983368.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/73000000/72280000/72279600/72279580/9509d0ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, bidet, towels](https://images.trvl-media.com/lodging/73000000/72280000/72279600/72279580/447e1de4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/73000000/72280000/72279600/72279580/4aba6ade.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, travel crib, free WiFi](https://images.trvl-media.com/lodging/73000000/72280000/72279600/72279580/05ff5304.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Colle di Val d'Elsa - Siena - Apt Blue - C Colle di Val d'Elsa 10/10 Exceptional (1) "Un vero e proprio appartamentino con camera da letto e soggiorno con angolo cottura perfettamente attrezzato. Bagno molto bello con doccia doppia. Comodissimo anche il check in on line che permette di arrivare quando si vuole dopo un cero orario" ![Italy](https://a.travel-assets.com/egds/marks/flags/it.svg) Francesco S. CA $130 CA $244 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Colle-Di-Val-DElsa-Hotels-Apartment.h72279580.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=2025-11-08&endDate=2025-11-09®ionId=603148&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Chianti Region Hotel Reviews ![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) ![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) ![Castello di Spaltenna- Small Luxury Hotels of the World](//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) ![Hotel Ristorante Alcide](//images.trvl-media.com/lodging/2000000/1410000/1402100/1402058/d779a567_y.jpg) ### Hotel Ristorante Alcide 10/10 Excellent "I highly recommended " [](https://expedia.ca/Poggibonsi-Hotels-Hotel-Ristorante-Alcide.h1402058.Hotel-Information) ![Castello di Fonterutoli Wine Resort](//images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/9f05cf5a_y.jpg) ### Castello di Fonterutoli Wine Resort 10/10 Excellent "It was a glorious place. So quaint, clean and rustic. Very relaxing and peaceful stay. Friendly team members and excellent wine. We met some friendly people on the wine tour. The breakfast was delicious! Many options for those who don’t eat pork and a beautiful location. This is a place to return for another vacation. I will be back! 😊 " [](https://expedia.ca/Castellina-In-Chianti-Hotels-Castello-Di-Fonterutoli.h5172395.Hotel-Information) ![Palazzo Leopoldo Dimora Storica & Spa](//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) ![Borgo Vescine](//images.trvl-media.com/lodging/2000000/1190000/1180600/1180553/8d2f3252_y.jpg) ### Borgo Vescine 10/10 Excellent "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. " [](https://expedia.ca/Radda-In-Chianti-Hotels-Il-Borgo-Di-Vescine.h1180553.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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