Title: Tuscany Winery Hotels from CA $231: 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://a.travel-assets.com/findyours-php/viewfinder/images/res70/157000/157252-Tuscany.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Tuscany Winery Hotels from CA $231 ![](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 Tuscany Winery Hotels Tonight [Oct 24 - Oct 25](https://www.expedia.ca/Hotel-Search?regionId=601686&startDate=2025-10-24&endDate=2025-10-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 25 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=601686&startDate=2025-10-25&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=601686&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=601686&startDate=2025-10-31&endDate=2025-11-02&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) ![Regional cuisine](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/bf56b5da.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) ![Villa, 2 Bedrooms | Living area](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/7c35f9bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castello Vicchiomaggio Greve in Chianti 9.4/10 Exceptional (369) "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 CA $253 CA $278 total includes taxes & fees Oct 25 - Oct 26 [](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](https://images.trvl-media.com/lodging/6000000/5180000/5172400/5172395/e04b84de.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) ### Castello di Fonterutoli Wine Resort Castellina in Chianti 9.4/10 Exceptional (191) "Amazing experience all around! Stayed for 2 nights!" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Matthew CA $237 CA $268 total includes taxes & fees Oct 28 - Oct 29 [](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/2000000/1190000/1180600/1180553/22162502.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) ![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 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 CA $433 CA $490 total includes taxes & fees Oct 29 - Oct 30 [](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) ![Billiards](https://images.trvl-media.com/lodging/3000000/2760000/2750300/2750235/9500aee5.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) ### Tenuta Santo Pietro Pienza 9.6/10 Exceptional (118) "Great countryside stay" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Josh CA $315 CA $354 total includes taxes & fees Oct 26 - Oct 27 [](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) ![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) ![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/5000000/4780000/4774100/4774015/09b92259.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castello Banfi - Il Borgo Montalcino 10/10 Exceptional (123) "The setting, scenery and hotel were 5 star plus!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Diana CA $1,271 CA $1,414 total includes taxes & fees Oct 25 - Oct 26 [](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) ![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) ![Junior Suite](https://images.trvl-media.com/lodging/5000000/4320000/4310500/4310479/b9811738.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 (268) "Nice place to stay for a few days. " ![Germany](https://a.travel-assets.com/egds/marks/flags/de.svg) Miles CA $204 CA $231 total includes taxes & fees Nov 4 - Nov 5 [](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) ![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) ![Executive Double Room, Patio | View from room](https://images.trvl-media.com/lodging/4000000/3560000/3556600/3556560/20f4cb97.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) ### 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 CA $412 CA $463 total includes taxes & fees Oct 26 - Oct 27 [](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) ![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) ![Classic Double Room](https://images.trvl-media.com/lodging/10000000/9780000/9778300/9778251/5696e650.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) ### 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/f6f6c579.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sauna, hot tub, Turkish bath, body treatments, deep-tissue massages](https://images.trvl-media.com/lodging/4000000/3610000/3605900/3605816/9b686be8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/4000000/3610000/3605900/3605816/4fd3ea89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sauna, hot tub, Turkish bath, body treatments, deep-tissue massages](https://images.trvl-media.com/lodging/4000000/3610000/3605900/3605816/60fdab27.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 CA $226 CA $259 total includes taxes & fees Oct 27 - Oct 28 [](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) ![Property entrance](https://images.trvl-media.com/lodging/3000000/2530000/2526600/2526551/ce02717a.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) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/3000000/2530000/2526600/2526551/74def047.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fattoria San Donato San Gimignano 9.4/10 Exceptional (59) "The place is very nice, in Toscana. Quiet, peacefull" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daisy [](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=2025-11-07&endDate=2025-11-08®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](//images.trvl-media.com/lodging/1000000/60000/54200/54104/ecd15007_y.jpg) ### Hotel Paris 10/10 Excellent "Excellent " [](https://expedia.ca/Florence-Hotels-Hotel-Paris.h54104.Hotel-Information) ![Garden Blue](//images.trvl-media.com/lodging/89000000/89000000/88999100/88999064/062077ea_y.jpg) ### Garden Blue 10/10 Excellent "it was a truly nice experience: friendly and attentive staff. Always willing to go the extra mile to assist. Cafeteria staff prepared nutritious and memorable breakfast. I shall book at the Blue Garden again. In the meantime you have gained my trust, confidence and recommendations. Kudos to all," [](https://expedia.ca/Florence-Hotels-Garden-Blue.h88999064.Hotel-Information) ![The Social Hub Florence Belfiore](//images.trvl-media.com/lodging/111000000/110560000/110551000/110550930/66ceba72_y.jpg) ### The Social Hub Florence Belfiore 10/10 Excellent "amazing place and clean close to everything" [](https://expedia.ca/Florence-Hotels-The-Social-Hub-Florence-Belfiore.h110550930.Hotel-Information) ![The Hoxton Florence](//images.trvl-media.com/lodging/105000000/104900000/104897200/104897196/e5c58994_y.jpg) ### The Hoxton Florence 10/10 Excellent "Great new hotel in a quiet area and about 10-15 min walk to center but further from other areas " [](https://expedia.ca/Florence-Hotels-The-Hoxton-Florence.h104897196.Hotel-Information) ![Solo Experience Hotel](//images.trvl-media.com/lodging/3000000/2540000/2533900/2533892/2466c367_y.jpg) ### Solo Experience Hotel 10/10 Excellent "Good spot in the heart of Florence near the train" [](https://expedia.ca/Florence-Hotels-Solo-Experience-Hotel.h2533892.Hotel-Information) ![Grand Hotel Baglioni](//images.trvl-media.com/lodging/1000000/10000/6400/6371/849fb031_y.jpg) ### Grand Hotel Baglioni 10/10 Excellent "Very nice hotel, wonderful staff. Only issue was room was a bit noisy when the window was open and warm when closed. Area outside is very crowded with people and cars. Hotel did offer to change rooms." [](https://expedia.ca/Florence-Hotels-Grand-Hotel-Baglioni.h6371.Hotel-Information) ![Ruby Bea Hotel Florence](//images.trvl-media.com/lodging/103000000/102430000/102429800/102429735/709afed8_y.jpg) ### Ruby Bea Hotel Florence 10/10 Excellent "Great hotel, well appointed and quiet rooms (despite being on a busy square), attentive staff and casual vibe.slightly out of the main action, but an easy 15 minute stroll to all the centre. Tram outside the front door makes it super accessible. " [](https://expedia.ca/Florence-Hotels-Ruby-Bea-Hotel-Florence.h102429735.Hotel-Information) ![Aurum Firenze](//images.trvl-media.com/lodging/29000000/28970000/28962000/28961941/26fd50f1_y.jpg) ### Aurum Firenze 10/10 Excellent "We were able to check-in early. It is walkable from Santa Maria Novella train station and so are the points of interest. When we arrived, the electric metal blinds was not working. Letitia gave us a sheet to temporarily give us privacy. When we came back from our tour the next day, it was already fixed. Great place to stay. Worth the money we paid for. Santa Maria Novella Basilica is close by. Worth visiting. Well recommended. " [](https://expedia.ca/Florence-Hotels-Aurum-Firenze.h28961941.Hotel-Information) ![c-hotels Ambasciatori](//images.trvl-media.com/lodging/1000000/10000/1900/1829/bddb8fbc_y.jpg) ### c-hotels Ambasciatori 10/10 Excellent "Very convenient to out of Florence day trips " [](https://expedia.ca/Florence-Hotels-C-Hotels-Ambasciatori.h1829.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) - 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