Title: Tuscany Winery Hotels : Book the Right Winery Hotels Room in Tuscany, Italy - Expedia.ca [Tuscany Travel Guide](https://expedia.ca/Tuscany.dx601686)[Tuscany Hotels](https://expedia.ca/Destinations-In-Tuscany.d601686.Hotel-Destinations)[Vacation Rentals in Tuscany](https://expedia.ca/Destinations-In-Tuscany.d601686.Vacation-Rental-Destinations)[Tuscany Flights](https://expedia.ca/Destinations-In-Tuscany.d601686.Flight-Destinations)[Tuscany Car Rentals](https://expedia.ca/Destinations-In-Tuscany.d601686.Car-Rental-Destinations)[Tuscany Vacations](https://expedia.ca/Tuscany.d601686.Destination-Travel-Guides) ![Montalcino which includes heritage architecture and a sunset](https://images.trvl-media.com/place/6025631/a4fff669-7ab2-4916-b5e4-83b0ec3a76bf.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6025631/a4fff669-7ab2-4916-b5e4-83b0ec3a76bf.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 ## Top Cities in Tuscany ![San Gimignano featuring street scenes and shopping as well as a large group of people](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/157000/157883-San-Gimignano.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### San Gimignano [](https://expedia.ca/San-Gimignano-Hotels-Winery-Hotel.0-0-d11091-tWineryHotel.Travel-Guide-Filter-Hotels) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/408000/408972-Florence.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Florence [](https://expedia.ca/Florence-Hotels-Winery-Hotel.0-0-d1222-tWineryHotel.Travel-Guide-Filter-Hotels) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/409000/409074-Siena.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Siena [](https://expedia.ca/Siena-Hotels-Winery-Hotel.0-0-d9821-tWineryHotel.Travel-Guide-Filter-Hotels) ![Leaning Tower which includes heritage architecture, a garden and heritage elements](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/58000/58146-Leaning-Tower.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Pisa [](https://expedia.ca/Pisa-Hotels-Winery-Hotel.0-0-d2877-tWineryHotel.Travel-Guide-Filter-Hotels) ![Livorno which includes a house](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/58000/58202-Livorno.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Livorno [](https://expedia.ca/Livorno-Hotels-Winery-Hotel.0-0-d178013-tWineryHotel.Travel-Guide-Filter-Hotels) ![Arezzo featuring a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/119000/119649-Arezzo-Province.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Arezzo [](https://expedia.ca/Arezzo-Hotels-Winery-Hotel.0-0-d11306-tWineryHotel.Travel-Guide-Filter-Hotels) ## Check availability on Tuscany Winery Hotels Tonight [Jan 15 - Jan 16](https://www.expedia.ca/Hotel-Search?regionId=601686&startDate=2026-01-15&endDate=2026-01-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 16 - Jan 17](https://www.expedia.ca/Hotel-Search?regionId=601686&startDate=2026-01-16&endDate=2026-01-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=601686&startDate=2026-01-16&endDate=2026-01-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=601686&startDate=2026-01-23&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Tuscany hotels with winery ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/62d09fdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa, 2 Bedrooms](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/88129386.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/373632fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/9c42f1e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castello Vicchiomaggio [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Castello-Vicchiomaggio.h7564854.Hotel-Information) Greve in Chianti 9.4/10 Exceptional (372 reviews) "Very special treat to stay here. We hope to return " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Cheyenne [](https://www.expedia.ca/Greve-In-Chianti-Hotels-Castello-Vicchiomaggio.h7564854.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/f80bb145.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; Italian cuisine, garden views ](https://images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/27a5f04f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Double or Twin Room](https://images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/9f80b6a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/70f4f37a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castello di Fonterutoli Wine Resort [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Castello-Di-Fonterutoli.h5172395.Hotel-Information) Castellina in Chianti 9.4/10 Exceptional (201 reviews) "Amazing experience all around! Stayed for 2 nights!" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Matthew [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Castello-Di-Fonterutoli.h5172395.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1190000/1180600/1180553/8e8f5330.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1190000/1180600/1180553/22162502.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) ### Borgo Vescine [](https://www.expedia.ca/Radda-In-Chianti-Hotels-Il-Borgo-Di-Vescine.h1180553.Hotel-Information) Radda in Chianti 9.4/10 Exceptional (244 reviews) "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) ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2760000/2750300/2750235/77df39f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/3000000/2760000/2750300/2750235/505c05f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/3000000/2760000/2750300/2750235/2f01bea3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Billiards](https://images.trvl-media.com/lodging/3000000/2760000/2750300/2750235/9500aee5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tenuta Santo Pietro [](https://www.expedia.ca/Pienza-Hotels-Tenuta-Santo-Pietro.h2750235.Hotel-Information) Pienza 9.6/10 Exceptional (119 reviews) "Great countryside stay" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Josh [](https://www.expedia.ca/Pienza-Hotels-Tenuta-Santo-Pietro.h2750235.Hotel-Information) ![Junior Suite | View from room](https://images.trvl-media.com/lodging/5000000/4780000/4774100/4774015/cda9c123.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/5000000/4780000/4774100/4774015/91a951f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/5000000/4780000/4774100/4774015/09b92259.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/5000000/4780000/4774100/4774015/4bbcb08d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castello Banfi - Il Borgo - Relais et Chateaux [](https://www.expedia.ca/Montalcino-Hotels-Castello-Banfi-Il-Borgo.h4774015.Hotel-Information) Montalcino 10/10 Exceptional (126 reviews) "The setting, scenery and hotel were 5 star plus!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Diana [](https://www.expedia.ca/Montalcino-Hotels-Castello-Banfi-Il-Borgo.h4774015.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/5000000/4320000/4310500/4310479/cd1e0f87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/5000000/4320000/4310500/4310479/6c794031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/5000000/4320000/4310500/4310479/3733c3a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite](https://images.trvl-media.com/lodging/5000000/4320000/4310500/4310479/b9811738.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relais Villa Grazianella - UNA Esperienze [](https://www.expedia.ca/Montepulciano-Hotels-Relais-Villa-Grazianella-UNA-Esperienze.h4310479.Hotel-Information) Montepulciano 9.8/10 Exceptional (279 reviews) "Very beautiful hotel & friendly staff" ![Switzerland](https://a.travel-assets.com/egds/marks/flags/ch.svg) Winona Mia [](https://www.expedia.ca/Montepulciano-Hotels-Relais-Villa-Grazianella-UNA-Esperienze.h4310479.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/4000000/3560000/3556600/3556560/bc613474.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/4000000/3560000/3556600/3556560/78e0602e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3560000/3556600/3556560/5e2100dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Snack bar](https://images.trvl-media.com/lodging/4000000/3560000/3556600/3556560/58e19d9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Locanda le Piazze [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Locanda-Le-Piazze.h3556560.Hotel-Information) Castellina in Chianti 9.8/10 Exceptional (183 reviews) "Absolutely gorgeous property!" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) David [](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Locanda-Le-Piazze.h3556560.Hotel-Information) ![Seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/10000000/9780000/9778300/9778251/51f9746c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite | View from room](https://images.trvl-media.com/lodging/10000000/9780000/9778300/9778251/17ca3949.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room (Superior)](https://images.trvl-media.com/lodging/10000000/9780000/9778300/9778251/27f8a5e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/10000000/9780000/9778300/9778251/07fedf6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Loggio Winery and Boutique Hotel [](https://www.expedia.ca/Cortona-Hotels-Villa-Loggio-Winery-And-Boutique-Hotel.h9778251.Hotel-Information) Cortona 10/10 Exceptional (3 reviews) "Staff was amazing. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Chloe [](https://www.expedia.ca/Cortona-Hotels-Villa-Loggio-Winery-And-Boutique-Hotel.h9778251.Hotel-Information) ![Sauna, hot tub, steam room, Turkish bath, body treatments, aromatherapy](https://images.trvl-media.com/lodging/4000000/3610000/3605900/3605816/4f1f3296.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3610000/3605900/3605816/4e351342.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sauna, hot tub, steam room, Turkish bath, body treatments, aromatherapy](https://images.trvl-media.com/lodging/4000000/3610000/3605900/3605816/43f57108.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3610000/3605900/3605816/f6f6c579.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Villa Campomaggio [](https://www.expedia.ca/Radda-In-Chianti-Hotels-Hotel-Villa-Campomaggio.h3605816.Hotel-Information) Radda in Chianti 9.2/10 Wonderful (164 reviews) "Amazing place, amazing people " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nitzan [](https://www.expedia.ca/Radda-In-Chianti-Hotels-Hotel-Villa-Campomaggio.h3605816.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2530000/2526600/2526551/8a2f5167.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/3000000/2530000/2526600/2526551/05fd2436.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily buffet breakfast (EUR 14 per person)](https://images.trvl-media.com/lodging/3000000/2530000/2526600/2526551/6af7a35c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/3000000/2530000/2526600/2526551/824d18c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fattoria San Donato [](https://www.expedia.ca/San-Gimignano-Hotels-Fattoria-San-Donato.h2526551.Hotel-Information) San Gimignano 9.4/10 Exceptional (59 reviews) "The people were so welcoming." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) HERBERT [](https://www.expedia.ca/San-Gimignano-Hotels-Fattoria-San-Donato.h2526551.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=2026-01-28&endDate=2026-01-29®ionId=601686&adults=2&location_highlights_explore=winery&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%2FDestinations-In-Tuscany-Winery-Hotel.0-0-d601686-tWineryHotel.Hotel-Filter-Destinations)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Tuscany-Winery-Hotel.0-0-d601686-tWineryHotel.Hotel-Filter-Destinations) ## Top Tuscany Hotel Reviews ![Orto De Medici Hotel](https://images.trvl-media.com/lodging/1000000/850000/849900/849839/c7d418e5_y.jpg) ### Orto De Medici Hotel 10/10 Excellent "Great location for touring Florence. Clean. Excellent breakfast! Staff booked our cabs and recommended restaurants that were very good. We can't wait to return." [](https://expedia.ca/Florence-Hotels-Orto-De-Medici-Hotel.h849839.Hotel-Information) ![Hotel Albani Firenze](https://images.trvl-media.com/lodging/1000000/30000/26000/25903/a7e1bd67_y.jpg) ### Hotel Albani Firenze 10/10 Excellent "I Wes interested with everything in hotel staff clean room breakfast fantastic service thanks so much " [](https://expedia.ca/Florence-Hotels-Hotel-Albani-Firenze.h25903.Hotel-Information) ![Hotel Grifone](https://images.trvl-media.com/lodging/1000000/530000/521300/521259/8c48791f_y.jpg) ### Hotel Grifone 10/10 Excellent "Rooms and common areas spotlessly clean. Quiet. Frequent bus transportation to the city center. Everything in the room worked as it should. Supermarket right around the corner." [](https://expedia.ca/Florence-Hotels-Hotel-Grifone.h521259.Hotel-Information) ![Hotel Delle Nazioni](https://images.trvl-media.com/lodging/1000000/930000/920200/920176/dd1e8db6_y.jpg) ### Hotel Delle Nazioni 10/10 Excellent "Very good " [](https://expedia.ca/Florence-Hotels-Hotel-Delle-Nazioni.h920176.Hotel-Information) ![Hotel Pendini](https://images.trvl-media.com/lodging/1000000/60000/54200/54105/2a00cb08_y.jpg) ### Hotel Pendini 10/10 Excellent "We had a wonderful stay at this hotel! The location is excellent—close to everything we wanted to see and do, which made getting around incredibly convenient. The hospitality truly stood out; the staff was warm, welcoming, and always willing to help with a smile. The room was comfortable and well-maintained, and we felt taken care of from check-in to check-out. We would definitely stay here again and highly recommend it to anyone looking for great service and a perfect location." [](https://expedia.ca/Florence-Hotels-Hotel-Pendini.h54105.Hotel-Information) ![The Market Urban Hotel](https://images.trvl-media.com/lodging/1000000/110000/108100/108028/7e915af7_y.jpg) ### The Market Urban Hotel 10/10 Excellent "The hotel’s location is perfect—just a 3-minute walk from the train station and a 5-minute walk from the historic center of Florence. The room is a bit small, but it is very clean." [](https://expedia.ca/Florence-Hotels-The-Market-Urban-Hotel.h108028.Hotel-Information) ![Bernini Palace](https://images.trvl-media.com/lodging/1000000/20000/14000/13999/84743cc7_y.jpg) ### Bernini Palace 10/10 Excellent "Absolutely Fantastic! Already booked another stay before this one was over. The staff, the history, the service and the location make this Hotel STAND OUT! " [](https://expedia.ca/Florence-Hotels-Bernini-Palace.h13999.Hotel-Information) ![ Hotel Calimala Florence](https://images.trvl-media.com/lodging/38000000/37960000/37955200/37955169/62707ba1_y.jpg) ### Hotel Calimala Florence 10/10 Excellent "Modern hotel with friendly staff in Great Location . " [](https://expedia.ca/Florence-Hotels-Hotel-Calimala.h37955169.Hotel-Information) ![Grand Hotel Baglioni](https://images.trvl-media.com/lodging/1000000/10000/6400/6371/849fb031_y.jpg) ### Grand Hotel Baglioni 10/10 Excellent "Very good hotel in a fantastic location. Meters from all the sites. Rooms and service excellent. Best breakfast in Italy. " [](https://expedia.ca/Florence-Hotels-Grand-Hotel-Baglioni.h6371.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [4 Star Hotels in Florence ](https://www.expedia.ca/4Star-Florence-Hotels.s40-0-d1222.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Florence ](https://www.expedia.ca/5Star-Florence-Hotels.s50-0-d1222.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Province of Florence ](https://www.expedia.ca/Destinations-In-Province-Of-Florence-Boutique-Hotel.0-0-d179893-tBoutiqueHotel.Hotel-Filter-Destinations) - [Lgbt Friendly Hotels in Province of Florence ](https://www.expedia.ca/Destinations-In-Province-Of-Florence-LGBT-Friendly-Hotel.0-0-d179893-tLGBTFriendlyHotel.Hotel-Filter-Destinations) - [Luxury Hotels in Province of Florence ](https://www.expedia.ca/Destinations-In-Province-Of-Florence-Luxury-Hotel.0-0-d179893-tLuxuryHotel.Hotel-Filter-Destinations) - [Mountain Hotels in Province of Florence ](https://www.expedia.ca/Destinations-In-Province-Of-Florence-Mountain-Hotels.0-0-d179893-tMountainHotels.Hotel-Filter-Destinations) - 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