Title: TOP Historic Hotels in Chianti Region for 2026 | Expedia.co.uk [Chianti Region Travel Guide](https://expedia.co.uk/Chianti-Region.dx603148)[Hotels in Chianti Region](https://expedia.co.uk/Chianti-Region-Hotels.d603148.Travel-Guide-Hotels)[Holiday Rentals in Chianti Region](https://expedia.co.uk/Chianti-Region-Holiday-Rentals.d603148.Travel-Guide-HolidayRentals)[Flights to Chianti Region](https://expedia.co.uk/Cheap-Flights-To-Chianti-Region.d603148.Travel-Guide-Flights)[Things to do in Chianti Region](https://expedia.co.uk/Things-To-Do-In-Chianti-Region.d603148.Travel-Guide-Activities)[Chianti Region Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Chianti-Region.d603148.Car-Hire-Guide)[Chianti Region Holidays](https://expedia.co.uk/Chianti-Region.d603148.Holidays-City-Breaks) ![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__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](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 [28 Jan - 29 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=603148&startDate=2026-01-28&endDate=2026-01-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [29 Jan - 30 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=603148&startDate=2026-01-29&endDate=2026-01-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [30 Jan - 1 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=603148&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [6 Feb - 8 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=603148&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chianti Region historic hotels ![Exterior detail](https://images.trvl-media.com/lodging/36000000/35080000/35073400/35073320/58996a54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/36000000/35080000/35073400/35073320/eb021f76.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/b1887ffe.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) ### UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK [](https://www.expedia.co.uk/Greve-In-Chianti-Hotels-UNIQUE-LARGE-TERRACE-WITH-VIEWS-TO-CHAINTI-VALLEY-AND-DRINK.h35073320.Hotel-Information) Ruffoli 9.4/10 Exceptional (20 reviews) "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 £141 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/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/c0ae1e50.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) ![Property grounds](https://images.trvl-media.com/lodging/31000000/30370000/30366000/30365985/74baafed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### CHIANTI VINEYARDS OLIVE GROVES FOOD TASTINGS SCENIC VIEWS [](https://www.expedia.co.uk/Greve-In-Chianti-Hotels-CHIANTI-VINEYARDS-OLIVE-GROVES-FOOD-TASTINGS-SCENIC-VIEWS.h30365985.Hotel-Information) Ruffoli 9.2/10 Wonderful (28 reviews) "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. £235 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Greve-In-Chianti-Hotels-CHIANTI-VINEYARDS-OLIVE-GROVES-FOOD-TASTINGS-SCENIC-VIEWS.h30365985.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/35000000/34110000/34102500/34102457/5d9ea4c0.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) ![Outdoor spa tub](https://images.trvl-media.com/lodging/35000000/34110000/34102500/34102457/0ebd1f06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34110000/34102500/34102457/e089714b.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 [](https://www.expedia.co.uk/Terranuova-Bracciolini-Hotels-Deluxe-Room-Nero-Su-Bianco-With-AC-And-Private-Bathroom-In-Villa-Le-Facezie-BB.h34102457.Hotel-Information) Terranuova Bracciolini 10/10 Exceptional (1 review) "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. £117 includes taxes & fees 29 Jan - 30 Jan [](https://www.expedia.co.uk/Terranuova-Bracciolini-Hotels-Deluxe-Room-Nero-Su-Bianco-With-AC-And-Private-Bathroom-In-Villa-Le-Facezie-BB.h34102457.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/68000000/67580000/67574900/67574832/d2d1c704.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, travel cot, free WiFi](https://images.trvl-media.com/lodging/68000000/67580000/67574900/67574832/cd820022.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) ![Interior](https://images.trvl-media.com/lodging/68000000/67580000/67574900/67574832/3562c29b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Old medieval apartment [](https://www.expedia.co.uk/Barberino-Tavarnelle-Hotels-Old-Medieval-Apartment.h67574832.Hotel-Information) San Donato 9.8/10 Exceptional (7 reviews) "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 £112 includes taxes & fees 29 Jan - 30 Jan [](https://www.expedia.co.uk/Barberino-Tavarnelle-Hotels-Old-Medieval-Apartment.h67574832.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/73000000/72280000/72279600/72279580/7e01a778.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![1 bedroom, in-room safe, travel cot, 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 [](https://www.expedia.co.uk/Colle-Di-Val-DElsa-Hotels-Apartment.h72279580.Hotel-Information) Colle di Val d'Elsa 10/10 Exceptional (2 reviews) "Super clean and a comfortable bed. Everything essential for making meals at home was provided. The host was very attentive and available by text. Housekeeping did an excellent job!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ALLAN £127 includes taxes & fees 29 Jan - 30 Jan [](https://www.expedia.co.uk/Colle-Di-Val-DElsa-Hotels-Apartment.h72279580.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/40000000/39970000/39961800/39961744/7470561f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/40000000/39970000/39961800/39961744/80ffd885.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/40000000/39970000/39961800/39961744/00d2d5a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/40000000/39970000/39961800/39961744/6e3158cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Suite Rosso di Sera with A/C and Private bathroom- Villa le Facezie B&B [](https://www.expedia.co.uk/Terranuova-Bracciolini-Hotels-Le-Facezie-Rosso-Di-Sera-Suite.h39961744.Hotel-Information) Terranuova Bracciolini £151 includes taxes & fees 31 Jan - 1 Feb [](https://www.expedia.co.uk/Terranuova-Bracciolini-Hotels-Le-Facezie-Rosso-Di-Sera-Suite.h39961744.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/40000000/39880000/39877200/39877147/a0626894.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/40000000/39880000/39877200/39877147/5e887fec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/40000000/39880000/39877200/39877147/3f811c84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/40000000/39880000/39877200/39877147/502c34fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Superior Settimo Cielo with A/C and Private Bathroom in Villa le Facezie B&B [](https://www.expedia.co.uk/Terranuova-Bracciolini-Hotels-Superior-Settimo-Cielo-With-AC-And-Private-Bathroom-In-Villa-Le-Facezie-BB.h39877147.Hotel-Information) Terranuova Bracciolini £132 includes taxes & fees 29 Jan - 30 Jan [](https://www.expedia.co.uk/Terranuova-Bracciolini-Hotels-Superior-Settimo-Cielo-With-AC-And-Private-Bathroom-In-Villa-Le-Facezie-BB.h39877147.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/28000000/27470000/27461900/27461842/c7076070.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/28000000/27470000/27461900/27461842/4eeaf647.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/28000000/27470000/27461900/27461842/1d63c974.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/28000000/27470000/27461900/27461842/bea6b45a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pleasant characteristic hayloft that has been renovated into holiday apartment in a part of the Chianti that is ideal for visiting the most important towns. [](https://www.expedia.co.uk/Monteriggioni-Hotels-Pleasant-Characteristic-Hayloft-That-Has-Been-Renovated-Into-Holiday-Apartment-In-A-Part-Of-The-Chianti-That-Is-Ideal-For-Visiting-The-Most-Important-Towns.h27461842.Hotel-Information) Monteriggioni 10/10 Exceptional (12 reviews) "Monteriggioni is the perfect location between Siena, San Gimignani, and roads to Chianti. The hosts Marcela, Enzo, and Alessandro really made us feel at home and comfortable. The property is beautiful, quiet, with unforgettable sunsets! Time at the pool is refreshing and relaxing, with beautiful views of the surrounding countryside. The authentic Italian kitchen was perfect for creating your own breakfasts and dinners. The bathrooms with showers have all you need, and the beds are really... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel D. £283 includes taxes & fees 4 Feb - 5 Feb [](https://www.expedia.co.uk/Monteriggioni-Hotels-Pleasant-Characteristic-Hayloft-That-Has-Been-Renovated-Into-Holiday-Apartment-In-A-Part-Of-The-Chianti-That-Is-Ideal-For-Visiting-The-Most-Important-Towns.h27461842.Hotel-Information) ![1 bedroom, in-room safe, travel cot, free WiFi](https://images.trvl-media.com/lodging/71000000/70510000/70501800/70501797/d853391b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/71000000/70510000/70501800/70501797/24b4407d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/71000000/70510000/70501800/70501797/4d2cd43e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Spa](https://images.trvl-media.com/lodging/71000000/70510000/70501800/70501797/dc09617d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Colle di Val d'Elsa - Siena - Apt White - D [](https://www.expedia.co.uk/Colle-Di-Val-DElsa-Hotels-Colle-Di-Val-DElsa-Siena-Apt-White-D.h70501797.Hotel-Information) Colle di Val d'Elsa £137 includes taxes & fees 10 Feb - 11 Feb [](https://www.expedia.co.uk/Colle-Di-Val-DElsa-Hotels-Colle-Di-Val-DElsa-Siena-Apt-White-D.h70501797.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.co.uk/Hotel-Search?startDate=2026-02-11&endDate=2026-02-12®ionId=603148&adults=2&specialized_stays_group_explore=historic_property&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.co.uk/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.co.uk/Colle-Di-Val-DElsa-Hotels-Hotel-Palazzo-San-Lorenzo-SPA.h3474921.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.co.uk/Castellina-In-Chianti-Hotels-Castello-Di-Fonterutoli.h5172395.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.co.uk/Poggibonsi-Hotels-Hotel-Toscana-Ambassador.h1429488.Hotel-Information) ![Agriturismo San Sano](https://images.trvl-media.com/lodging/2000000/1500000/1492000/1491964/f2375def_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.co.uk/Gaiole-In-Chianti-Hotels-Hotel-Residence-San-Sano.h1491964.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.co.uk/Greve-In-Chianti-Hotels-Castello-Vicchiomaggio.h7564854.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.co.uk/Barberino-Tavarnelle-Hotels-COMO-Castello-Del-Nero.h1279768.Hotel-Information) ![Il Borro - Relais & Châteaux](https://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.co.uk/Loro-Ciuffenna-Hotels-Il-Borro-Relais-Chateaux.h5585638.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.co.uk/Gaiole-In-Chianti-Hotels-Castello-Di-Spaltenna.h2540741.Hotel-Information) ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - Other - More ways to book - [3 Star Hotels in Radda in Chianti ](https://www.expedia.co.uk/3Star-Radda-In-Chianti-Hotels.s30-0-d601693.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Castellina in Chianti ](https://www.expedia.co.uk/Castellina-In-Chianti-Hotels-Adults-Only-Resorts.0-0-d55534-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Beach Resorts & in Castellina in Chianti ](https://www.expedia.co.uk/Castellina-In-Chianti-Hotels-Beach-Hotels.0-0-d55534-tBeachHotels.Travel-Guide-Filter-Hotels) - [Hotels with Restaurant in Castellina in Chianti ](https://www.expedia.co.uk/Castellina-In-Chianti-Hotels-Hotel-With-Restaurant.0-0-d55534-thotelwithrestaurant.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Castellina in Chianti ](https://www.expedia.co.uk/Castellina-In-Chianti-Hotels-Luxury-Hotel.0-0-d55534-tLuxuryHotel.Travel-Guide-Filter-Hotels) - 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