Title: Tuscany Winery Hotels from CA $181: 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 $181 - ![](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 [Nov 26 - Nov 27](https://www.expedia.ca/Hotel-Search?regionId=601686&startDate=2025-11-26&endDate=2025-11-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 27 - Nov 28](https://www.expedia.ca/Hotel-Search?regionId=601686&startDate=2025-11-27&endDate=2025-11-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=601686&startDate=2025-11-28&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=601686&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Tuscany Winery Hotels ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/3167b59e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/d55388f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Regional cuisine](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/bf56b5da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/da2e11e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castello Vicchiomaggio Greve in Chianti 9.4/10 Exceptional (370) "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) ![Breakfast, lunch, dinner served; Italian cuisine, garden views ](https://images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/9f05cf5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic Suite, Vineyard View | Vineyard view](https://images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/91065266.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) ![Panoramic Suite, Vineyard View](https://images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/e04b84de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castello di Fonterutoli Wine Resort Castellina in Chianti 9.4/10 Exceptional (198) "Clean room, courteous staff, and good winery" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sangchun CA $211 CA $239 total includes taxes & fees Nov 27 - Nov 28 [](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) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/2000000/1190000/1180600/1180553/068bc6ab.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 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) ![Exclusive Villa, 2 Bedrooms, Garden View, Annex Building | Terrace/patio](https://images.trvl-media.com/lodging/3000000/2760000/2750300/2750235/4fa44438.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/3000000/2760000/2750300/2750235/a71dc3ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive Villa, 2 Bedrooms, Garden View, Annex Building](https://images.trvl-media.com/lodging/3000000/2760000/2750300/2750235/42a0569c.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 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) ![2 restaurants, lunch, dinner served; Italian cuisine](https://images.trvl-media.com/lodging/5000000/4780000/4774100/4774015/89af6209.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, lunch, dinner served; Italian cuisine](https://images.trvl-media.com/lodging/5000000/4780000/4774100/4774015/554821c2.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) ### Castello Banfi - Il Borgo - Relais et Chateaux Montalcino 10/10 Exceptional (125) "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) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/5000000/4320000/4310500/4310479/8b3fbbcc.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) ![Daily buffet breakfast (EUR 12 per person)](https://images.trvl-media.com/lodging/5000000/4320000/4310500/4310479/b28f1d5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/5000000/4320000/4310500/4310479/cd1e0f87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relais Villa Grazianella - UNA Esperienze Montepulciano 9.8/10 Exceptional (275) "Great room and service" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ALFREDO CA $159 CA $181 total includes taxes & fees Nov 27 - Nov 28 [](https://www.expedia.ca/Montepulciano-Hotels-Relais-Villa-Grazianella-UNA-Esperienze.h4310479.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/4000000/3560000/3556600/3556560/ac9c98a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Minibar, in-room safe, desk, free WiFi](https://images.trvl-media.com/lodging/4000000/3560000/3556600/3556560/57d93a90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/4000000/3560000/3556600/3556560/e1345488.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/e4212b2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Locanda le Piazze 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) ![View from property](https://images.trvl-media.com/lodging/10000000/9780000/9778300/9778251/c95e5742.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/10000000/9780000/9778300/9778251/f1e3329a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Bathtub | Private kitchen](https://images.trvl-media.com/lodging/10000000/9780000/9778300/9778251/88cd1bb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/10000000/9780000/9778300/9778251/463c0685.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Loggio Winery and Boutique Hotel 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) ![Exterior](https://images.trvl-media.com/lodging/4000000/3610000/3605900/3605816/6dc1f337.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/4000000/3610000/3605900/3605816/d5b6b0d7.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) ![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) ### Hotel Villa Campomaggio Radda in Chianti 9.2/10 Wonderful (163) "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) ![Restaurant](https://images.trvl-media.com/lodging/3000000/2530000/2526600/2526551/824d18c1.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) ![Property entrance](https://images.trvl-media.com/lodging/3000000/2530000/2526600/2526551/ce02717a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/3000000/2530000/2526600/2526551/c8e9b8f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fattoria San Donato 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 CA $200 CA $228 total includes taxes & fees Nov 30 - Dec 1 [](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=2025-12-10&endDate=2025-12-11®ionId=601686&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AFFINITY_BF_PROMO_601686) ![](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 ![Grand Hotel Cavour](https://images.trvl-media.com/lodging/1000000/20000/11000/10993/50470bbc_y.jpg) ### Grand Hotel Cavour 10/10 Excellent "Check-in was very well done. Folks were professional, helpful, and accommodating." [](https://expedia.ca/Florence-Hotels-Grand-Hotel-Cavour.h10993.Hotel-Information) ![IQ Hotel Firenze](https://images.trvl-media.com/lodging/90000000/89040000/89035100/89035039/72f32f77_y.jpg) ### IQ Hotel Firenze 10/10 Excellent "Room was clean and staff was friendly and helpful. Overall we had an amazing experience there. " [](https://expedia.ca/Florence-Hotels-IQ-Hotel-Firenze.h89035039.Hotel-Information) ![Bernini Palace](https://images.trvl-media.com/lodging/1000000/20000/14000/13999/84743cc7_y.jpg) ### Bernini Palace 10/10 Excellent "Spotless room, fantastic location, courteous staff" [](https://expedia.ca/Florence-Hotels-Bernini-Palace.h13999.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 "Everything was great. Breakfast and the staff were really good and the front desk was friendly and helpful Location was perfect for walking to main attractions in Florence " [](https://expedia.ca/Florence-Hotels-The-Market-Urban-Hotel.h108028.Hotel-Information) ![ Hotel Calimala Florence](https://images.trvl-media.com/lodging/38000000/37960000/37955200/37955169/62707ba1_y.jpg) ### Hotel Calimala Florence 10/10 Excellent "The rooftop bar and dining was lovely. The front desk staff was friendly and attentive. Our view out of the window was enchanting. The decor was stylish, elegant, and fun all wrapped up. " [](https://expedia.ca/Florence-Hotels-Hotel-Calimala.h37955169.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 "Clean room" [](https://expedia.ca/Florence-Hotels-25hours-Hotel-Piazza-San-Paolino.h70128094.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 location and place algo breakfast was super complete" [](https://expedia.ca/Florence-Hotels-Orto-De-Medici-Hotel.h849839.Hotel-Information) ![Hotel Bologna](https://images.trvl-media.com/lodging/1000000/920000/914300/914236/647ffe61_y.jpg) ### Hotel Bologna 10/10 Excellent "Great location, within walking distance of the train station and major attractions. The staff were very pleasant and helpful. The room was spotless but could have used some refurbishing." [](https://expedia.ca/Pisa-Hotels-Hotel-Bologna.h914236.Hotel-Information) ![Art Hotel Villa Agape](https://images.trvl-media.com/lodging/11000000/10510000/10507800/10507728/34e550c1_y.jpg) ### Art Hotel Villa Agape 10/10 Excellent "Property is beautiful and well located. Staff was very helpful and friendly! 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