Title: Book the Best Chianti Region WINERY Hotels in 2026 | 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 availability on Chianti Region Winery Hotels Tonight [Jan 22 - Jan 23](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-01-22&endDate=2026-01-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 23 - Jan 24](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-01-23&endDate=2026-01-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-01-23&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chianti Region hotels with winery ![Reception](https://images.trvl-media.com/lodging/21000000/20490000/20484000/20483959/4eac4992.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, minibar, in-room safe, individually decorated](https://images.trvl-media.com/lodging/21000000/20490000/20484000/20483959/4eeae5eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/21000000/20490000/20484000/20483959/56ce48bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/21000000/20490000/20484000/20483959/4d9792cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Salvadonica - Borgo del Chianti [](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Salvadonica.h20483959.Hotel-Information) San Casciano in Val di Pesa 9.6/10 Exceptional (265 reviews) "One of the finest boutique hotels I have ever stayed in. The hosts, the view, the room, the food they serve, the location is all memorable. The stay was the highlight of our trip to Florence ." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $137 CA $157 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Salvadonica.h20483959.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/8a9d9969.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/46476210.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; Italian cuisine, alfresco dining ](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/a55956cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/10000000/9800000/9797700/9797642/d6652f62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Certosa di Pontignano [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-La-Certosa-Di-Pontignano.h9797642.Hotel-Information) Castelnuovo Berardenga 9.6/10 Exceptional (508 reviews) "Excellent place to stay even for the next time. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Xuejie CA $151 CA $173 total includes taxes & fees Feb 14 - Feb 15 [](https://www.expedia.ca/Castelnuovo-Berardenga-Hotels-La-Certosa-Di-Pontignano.h9797642.Hotel-Information) ![Seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/3000000/2540000/2537900/2537801/089cca52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch and dinner served, alfresco dining ](https://images.trvl-media.com/lodging/3000000/2540000/2537900/2537801/afca094e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Winery](https://images.trvl-media.com/lodging/3000000/2540000/2537900/2537801/cbeec78c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2540000/2537900/2537801/f5b61d12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castello di Meleto [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Castello-Di-Meleto.h2537801.Hotel-Information) Gaiole in Chianti 8.8/10 Excellent (93 reviews) "We had a great time" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anna CA $215 CA $249 total includes taxes & fees Jan 23 - Jan 24 [](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Castello-Di-Meleto.h2537801.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/5000000/4900000/4890100/4890092/f9f34d83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/5000000/4900000/4890100/4890092/ff2e2ae0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4900000/4890100/4890092/67b6533a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 9:00 AM to 7:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/5000000/4900000/4890100/4890092/d8b69484.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Torraccia di Chiusi [](https://www.expedia.ca/San-Gimignano-Hotels-Torraccia-Di-Chiusi.h4890092.Hotel-Information) San Gimignano 10/10 Exceptional (97 reviews) "A beautiful base for exploring Tuscany away from the crowds." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anthony CA $257 CA $291 total includes taxes & fees Feb 20 - Feb 21 [](https://www.expedia.ca/San-Gimignano-Hotels-Torraccia-Di-Chiusi.h4890092.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/120000000/119330000/119324400/119324317/w2532h1132x0y19-eb15f7b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/120000000/119330000/119324400/119324317/dd89fac3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/120000000/119330000/119324400/119324317/a88420d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/120000000/119330000/119324400/119324317/6cf9f8a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Agriturismo Montemagni di Sopra [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Agriturismo-Montemagni-Di-Sopra.h119324317.Hotel-Information) Greve in Chianti 9.0/10 Wonderful (8 reviews) "The hostess is very accommodating and sweet. The beds were incredibly comfy and shower was spacious. A very lovely and peaceful stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rachel CA $119 CA $138 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Agriturismo-Montemagni-Di-Sopra.h119324317.Hotel-Information) ![Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/12000000/11050000/11047100/11047087/58b438dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/12000000/11050000/11047100/11047087/d2ad0eb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/12000000/11050000/11047100/11047087/f80e256a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/12000000/11050000/11047100/11047087/e3a4df1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Agriturismo Nerbona [](https://www.expedia.ca/Colle-Di-Val-DElsa-Hotels-Agriturismo-Nerbona.h11047087.Hotel-Information) Colle di Val d'Elsa 9.6/10 Exceptional (18 reviews) "Very nice place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JULISSA CA $131 CA $148 total includes taxes & fees Feb 21 - Feb 22 [](https://www.expedia.ca/Colle-Di-Val-DElsa-Hotels-Agriturismo-Nerbona.h11047087.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/97000000/96090000/96089000/96088992/c1317286.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive Studio Suite, 1 Bedroom, Hot Tub, Garden View](https://images.trvl-media.com/lodging/97000000/96090000/96089000/96088992/b9a4ef80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/97000000/96090000/96089000/96088992/81f70485.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool views ](https://images.trvl-media.com/lodging/97000000/96090000/96089000/96088992/8edfd189.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casa di Palaia [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Casa-Di-Palaia.h96088992.Hotel-Information) Greve in Chianti 10/10 Exceptional (22 reviews) "Very well located in the heart if the Tuscany region." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eli CA $119 CA $137 total includes taxes & fees Feb 18 - Feb 19 [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Casa-Di-Palaia.h96088992.Hotel-Information) ![Horseback riding](https://images.trvl-media.com/lodging/6000000/5590000/5585700/5585638/fb1bfe8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5590000/5585700/5585638/fa2ac4f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5590000/5585700/5585638/5b35f6b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5590000/5585700/5585638/00ea9987.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Il Borro - Relais & Châteaux [](https://www.expedia.ca/Loro-Ciuffenna-Hotels-Il-Borro-Relais-Chateaux.h5585638.Hotel-Information) Loro Ciuffenna 9.2/10 Wonderful (99 reviews) "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" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Ian CA $657 CA $723 total includes taxes & fees Feb 16 - Feb 17 [](https://www.expedia.ca/Loro-Ciuffenna-Hotels-Il-Borro-Relais-Chateaux.h5585638.Hotel-Information) ![Dinner served, Regional cuisine](https://images.trvl-media.com/lodging/56000000/55020000/55015700/55015679/028e9fba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/56000000/55020000/55015700/55015679/2a2eb237.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/56000000/55020000/55015700/55015679/87ab5e1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/56000000/55020000/55015700/55015679/w1845h1003x163y0-1ddc19dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Agriturismo La Posta Reale [](https://www.expedia.ca/Castiglion-Fibocchi-Hotels-Agriturismo-La-Posta-Reale.h55015679.Hotel-Information) Castiglion Fibocchi 9.0/10 Wonderful (2 reviews) "Our host was very attentive and lovely. She invited us to a very nice evening wine party on-site aside of a small lake. It was quite charming. It was also nice to see the vineyards and olive trees. One downside was no A/C as advertised, but we had fans. Still very quaint." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael [](https://www.expedia.ca/Castiglion-Fibocchi-Hotels-Agriturismo-La-Posta-Reale.h55015679.Hotel-Information) ![2 restaurants, breakfast, lunch, dinner served; Italian cuisine](https://images.trvl-media.com/lodging/1000000/900000/891700/891661/f41faf16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples treatment rooms, sauna, hot tub, steam room, Turkish bath](https://images.trvl-media.com/lodging/1000000/900000/891700/891661/ff372f94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/900000/891700/891661/c3549fd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/900000/891700/891661/af2e1f78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Casagrande Resort & SPA [](https://www.expedia.ca/Figline-E-Incisa-Valdarno-Hotels-Villa-Casagrande-Resort-SPA.h891661.Hotel-Information) Figline e Incisa Valdarno 9.2/10 Wonderful (378 reviews) "Always beautiful when I stay here, staff are helpful and every room clean and tidy " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Claire CA $139 CA $156 total includes taxes & fees Feb 10 - Feb 11 [](https://www.expedia.ca/Figline-E-Incisa-Valdarno-Hotels-Villa-Casagrande-Resort-SPA.h891661.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=2026-02-05&endDate=2026-02-06®ionId=603148&adults=2&location_highlights_explore=winery&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.ca/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.ca/Colle-Di-Val-DElsa-Hotels-Hotel-Palazzo-San-Lorenzo-SPA.h3474921.Hotel-Information) ![Villa San Lucchese](https://images.trvl-media.com/lodging/2000000/1690000/1685900/1685892/f05836b4_y.jpg) ### Villa San Lucchese 10/10 Excellent "Beautiful place Great service " [](https://expedia.ca/Poggibonsi-Hotels-Villa-San-Lucchese.h1685892.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.ca/Castellina-In-Chianti-Hotels-Castello-Di-Fonterutoli.h5172395.Hotel-Information) ![Hotel Borgo di Cortefreda Relais](https://images.trvl-media.com/lodging/2000000/1220000/1216500/1216478/288cff0c_y.jpg) ### Hotel Borgo di Cortefreda Relais 10/10 Excellent "The hotel and services exceeded my expectations." [](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) ### 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) ![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.ca/Greve-In-Chianti-Hotels-Castello-Vicchiomaggio.h7564854.Hotel-Information) ![Villa Castiglione](https://images.trvl-media.com/lodging/2000000/1350000/1348200/1348125/dbdc1d6b_y.jpg) ### Villa Castiglione 10/10 Excellent "Nice and cute place. Great price. " [](https://expedia.ca/Impruneta-Hotels-Villa-Castiglione.h1348125.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) ## 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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