Title: Tuscany Winery Hotels from CA $229: 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) # Tuscany Winery Hotels from CA $229 - ![](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 ![](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) ![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) ## Check availability on Tuscany Winery Hotels Tonight [Dec 11 - Dec 12](https://www.expedia.ca/Hotel-Search?regionId=601686&startDate=2025-12-11&endDate=2025-12-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 12 - Dec 13](https://www.expedia.ca/Hotel-Search?regionId=601686&startDate=2025-12-12&endDate=2025-12-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=601686&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=601686&startDate=2025-12-19&endDate=2025-12-21&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) ![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) ![Garden](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/29f2f09e.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) "Beautiful grounds. Room was spacious and the breakfast was delicious. Very friendly staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Devin [](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) ![Meeting facility](https://images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/9932f5d5.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) ![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) ### 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 (200) "Clean room, courteous staff, and good winery" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sangchun CA $256 CA $288 total includes taxes & fees Dec 14 - Dec 15 [](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) ![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) ![Interior](https://images.trvl-media.com/lodging/2000000/1190000/1180600/1180553/89fdd299.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) ### 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) "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) ![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) ![Restaurant](https://images.trvl-media.com/lodging/3000000/2760000/2750300/2750235/1f4e227d.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) "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/5000000/4780000/4774100/4774015/09b92259.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) ![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) "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) ![Interior detail](https://images.trvl-media.com/lodging/5000000/4320000/4310500/4310479/3733c3a3.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) ![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 (278) "Great room and service" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ALFREDO CA $202 CA $229 total includes taxes & fees Dec 13 - Dec 14 [](https://www.expedia.ca/Montepulciano-Hotels-Relais-Villa-Grazianella-UNA-Esperienze.h4310479.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/4000000/3560000/3556600/3556560/51cce0d9.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) ![Exterior](https://images.trvl-media.com/lodging/4000000/3560000/3556600/3556560/7e0de83a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/4000000/3560000/3556600/3556560/1ea3baa7.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) "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) ![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) ![Breakfast area](https://images.trvl-media.com/lodging/10000000/9780000/9778300/9778251/a83f54c9.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) "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) ![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/b7219039.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) "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) ![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) ![Double Room | Living area](https://images.trvl-media.com/lodging/3000000/2530000/2526600/2526551/351377de.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) "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=2025-12-25&endDate=2025-12-26®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 ![Hotel Paris](https://images.trvl-media.com/lodging/1000000/60000/54200/54104/ecd15007_y.jpg) ### Hotel Paris 10/10 Excellent "When I visit Florence I always stay here. Lovely front desk staff, l complimentary coffee and snacks, breakfast. Large elegant rooms! Excellent location. Good value. Grazie Mille!" [](https://expedia.ca/Florence-Hotels-Hotel-Paris.h54104.Hotel-Information) ![Solo Experience Hotel](https://images.trvl-media.com/lodging/3000000/2540000/2533900/2533892/2466c367_y.jpg) ### Solo Experience Hotel 10/10 Excellent "Room was clean and large. Staff was very helpful. Great location." [](https://expedia.ca/Florence-Hotels-Solo-Experience-Hotel.h2533892.Hotel-Information) ![25hours Hotel Florence Piazza San Paolino](https://images.trvl-media.com/lodging/71000000/70130000/70128100/70128094/63ed60b3_y.jpg) ### 25hours Hotel Florence Piazza San Paolino 10/10 Excellent "so in love with this hotel, after walking all day long, to come home to such a genuinely cute environment felt great. " [](https://expedia.ca/Florence-Hotels-25hours-Hotel-Piazza-San-Paolino.h70128094.Hotel-Information) ![Bernini Palace](https://images.trvl-media.com/lodging/1000000/20000/14000/13999/84743cc7_y.jpg) ### Bernini Palace 10/10 Excellent "Fresh breakfast " [](https://expedia.ca/Florence-Hotels-Bernini-Palace.h13999.Hotel-Information) ![The Social Hub Florence Lavagnini](https://images.trvl-media.com/lodging/24000000/23200000/23198300/23198289/fdc60d68_y.jpg) ### The Social Hub Florence Lavagnini 10/10 Excellent "Super friendly staff! Great location! " [](https://expedia.ca/Florence-Hotels-The-Social-Hub-Florence-Lavagnini.h23198289.Hotel-Information) ![Il Rivalta - Place of Charme](https://images.trvl-media.com/lodging/46000000/45800000/45790300/45790281/a67d0954_y.jpg) ### Il Rivalta - Place of Charme 10/10 Excellent "Everything was great 😃" [](https://expedia.ca/Florence-Hotels-Alfieri-Signature-Suites.h45790281.Hotel-Information) ![IQ Hotel Firenze](https://images.trvl-media.com/lodging/90000000/89040000/89035100/89035039/72f32f77_y.jpg) ### IQ Hotel Firenze 10/10 Excellent "Excellent " [](https://expedia.ca/Florence-Hotels-IQ-Hotel-Firenze.h89035039.Hotel-Information) ![Grand Hotel Cavour](https://images.trvl-media.com/lodging/1000000/20000/11000/10993/50470bbc_y.jpg) ### Grand Hotel Cavour 10/10 Excellent "Can't say enough amazing things about this hotel. Location is prime, staff was professional and courteous, breakfast service was superb, rooms were very clean and comfortable. Amazing experience overall. Will definitely be coming back." [](https://expedia.ca/Florence-Hotels-Grand-Hotel-Cavour.h10993.Hotel-Information) ![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 place to stay. Close to the historical centre of Florence. Staff was friendly and the amenities were good. " [](https://expedia.ca/Florence-Hotels-Orto-De-Medici-Hotel.h849839.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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