Title: Book the Best Val d'Orcia WINERY Hotels in 2025 | Expedia.ca [Val d'Orcia Travel Guide](https://expedia.ca/Val-DOrcia.dx6047918)[Hotels in Val d'Orcia](https://expedia.ca/Val-DOrcia-Hotels.d6047918.Travel-Guide-Hotels)[Vacation Rentals in Val d'Orcia](https://expedia.ca/Val-DOrcia-Vacation-Rentals.d6047918.Travel-Guide-VacationRentals)[Flights to Val d'Orcia](https://expedia.ca/Cheap-Flights-To-Val-DOrcia.d6047918.Travel-Guide-Flights)[Val d'Orcia Car Rentals](https://expedia.ca/Car-Rentals-In-Val-DOrcia.d6047918.Car-Rental-Guide)[Val d'Orcia Vacation Packages](https://expedia.ca/Val-DOrcia.d6047918.Destination-Travel-Guides) ![Cathedral of Pienza featuring religious elements, a church or cathedral and heritage elements](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/208000/208193-Cathedral-Of-Pienza.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Val d'Orcia - ![](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 Val d'Orcia Winery Hotels Tonight [Oct 31 - Nov 1](https://www.expedia.ca/Hotel-Search?regionId=6047918&startDate=2025-10-31&endDate=2025-11-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 1 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6047918&startDate=2025-11-01&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6047918&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6047918&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Val d'Orcia Winery Hotels ![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) ![Exclusive Villa, 2 Bedrooms, Garden View, Annex Building | Private kitchen](https://images.trvl-media.com/lodging/3000000/2760000/2750300/2750235/d9be60a9.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 (118) "Great countryside stay" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Josh CA $317 CA $356 total includes taxes & fees Nov 8 - Nov 9 [](https://www.expedia.ca/Pienza-Hotels-Tenuta-Santo-Pietro.h2750235.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/37000000/36330000/36326000/36325942/819a9035.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite Deluxe | View from room](https://images.trvl-media.com/lodging/37000000/36330000/36326000/36325942/b41e8535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite Deluxe | View from room](https://images.trvl-media.com/lodging/37000000/36330000/36326000/36325942/e4c153b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite Deluxe](https://images.trvl-media.com/lodging/37000000/36330000/36326000/36325942/767a162a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Capanna Suites Montalcino 9.8/10 Exceptional (125) "Absolutely amazing resort with amazing staff and service. Great food and beautiful spa experience. Highly reccommend anyone going to Tuscany to book here - you will not be disappointed ! " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Megan [](https://www.expedia.ca/Montalcino-Hotels-Capanna-Suites.h36325942.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/76000000/75750000/75743000/75742935/6d575777.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/76000000/75750000/75743000/75742935/935edd00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/76000000/75750000/75743000/75742935/a3596891.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room](https://images.trvl-media.com/lodging/76000000/75750000/75743000/75742935/8615c53d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Le Prata - Residenza del Vescovo Montalcino 10/10 Exceptional (68) "Incredible stay!" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Tomasz CA $484 CA $549 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Montalcino-Hotels-Winery-Boutique-Hotel-Villa-Le-Prata.h75742935.Hotel-Information) ![Spa](https://images.trvl-media.com/lodging/43000000/42580000/42576200/42576161/eb100684.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/43000000/42580000/42576200/42576161/d080f76f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Suite](https://images.trvl-media.com/lodging/43000000/42580000/42576200/42576161/920621bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/43000000/42580000/42576200/42576161/aad56975.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mastrojanni Relais Montalcino 9.8/10 Exceptional (59) "This is the most magical and beautiful property in Tuscany with amazing food and service. The guests talk about how they come back every year to this resort The views from the pool are the best in this area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura [](https://www.expedia.ca/Montalcino-Hotels-Relais-Mastrojanni.h42576161.Hotel-Information) ![Seasonal outdoor pool, open 9:30 AM to 7:30 PM, pool umbrellas](https://images.trvl-media.com/lodging/6000000/5220000/5218800/5218727/f577db3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic Apartment | Living area](https://images.trvl-media.com/lodging/6000000/5220000/5218800/5218727/76f21148.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5220000/5218800/5218727/96861552.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/6000000/5220000/5218800/5218727/3bef8f3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Le Ragnaie Montalcino 9.2/10 Wonderful (321) "A beautiful property!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alyss CA $121 CA $149 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Montalcino-Hotels-Agriturismo-Le-Ragnaie.h5218727.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/23000000/22950000/22946200/22946136/44c52963.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/23000000/22950000/22946200/22946136/4cc1ef4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/23000000/22950000/22946200/22946136/b2818bfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor banquet area](https://images.trvl-media.com/lodging/23000000/22950000/22946200/22946136/48aac8a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Agriturismo Il Macchione Pienza 9.6/10 Exceptional (55) "Lovely small hotel, large comfortable rooms with good facilities. Easy parking nice pool and Francesco, the owner, really helpful. Very good breakfast you largely pre-order " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) James [](https://www.expedia.ca/Pienza-Hotels-Agriturismo-Il-Macchione.h22946136.Hotel-Information) ![Land view from property](https://images.trvl-media.com/lodging/3000000/2530000/2525700/2525690/e0c5b2be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/3000000/2530000/2525700/2525690/7c006ed3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/3000000/2530000/2525700/2525690/50f526cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/3000000/2530000/2525700/2525690/900ab7d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Corsignano Pienza 9.4/10 Exceptional (325) "Excellent location, good service, nice rooms. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mirnes CA $191 CA $220 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Pienza-Hotels-Hotel-Corsignano.h2525690.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) "Great property and excellent dining options. I had to cut one star due reception " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Virendra CA $1,265 CA $1,407 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Montalcino-Hotels-Castello-Banfi-Il-Borgo.h4774015.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/108000000/107620000/107617500/107617451/130faa5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi](https://images.trvl-media.com/lodging/108000000/107620000/107617500/107617451/402d617f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi](https://images.trvl-media.com/lodging/108000000/107620000/107617500/107617451/548d8c36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107620000/107617500/107617451/f4393a11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wine Estate Paradiso di Cacuci Montalcino 7.4/10 Good (3) "They overbooked the wine vineyard and had me stay in their hotel in Montalcino. They didn’t charge me for the stay but it was inconvenient and it wasn’t the stay that i planned. The restaurant next door that they recommended wasn’t what i was looking for. I wantwd a classic tuscan meal." ![Italy](https://a.travel-assets.com/egds/marks/flags/it.svg) Tony CA $367 CA $420 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Montalcino-Hotels-Wine-Estate-Paradiso-Di-Cacuci.h107617451.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/2000000/1040000/1037900/1037832/87359911.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite Terrace (UNESCO view) | Living area](https://images.trvl-media.com/lodging/2000000/1040000/1037900/1037832/9be56e31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/2000000/1040000/1037900/1037832/56195c00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/2000000/1040000/1037900/1037832/5f1c53d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castello di Velona Resort Thermal SPA & Winery Montalcino 9.0/10 Wonderful (335) "Absolutely stunning property and an exceptional staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David [](https://www.expedia.ca/Montalcino-Hotels-Castello-Di-Velona-Resort-The-Leading-Hotels-Of-The-World.h1037832.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=2025-11-14&endDate=2025-11-15®ionId=6047918&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Val d'Orcia Hotel Reviews ![Castello di Velona Resort Thermal SPA & Winery](//images.trvl-media.com/lodging/2000000/1040000/1037900/1037832/87359911_y.jpg) ### Castello di Velona Resort Thermal SPA & Winery 10/10 Excellent "Everything was 5 star. It’s like living in a castle in the sky with hot thermal pools everywhere and amazing food. We loved our outdoor patio with the sunset view of the panorama." [](https://expedia.ca/Montalcino-Hotels-Castello-Di-Velona-Resort-The-Leading-Hotels-Of-The-World.h1037832.Hotel-Information) ![Hotel Dei Capitani](//images.trvl-media.com/lodging/3000000/2530000/2520200/2520185/156cc4b3_y.jpg) ### Hotel Dei Capitani 10/10 Excellent "It’s a lovely hotel. Reception was nice and the room very clean with an incredible view out the window of the valley behind. No balcony but a Juliet railing with large opening windows. The breakfast buffet was excellent, self serve with exception of coffee which was served by a very pleasant waiter. Parking is a bit of challenge in a steeply sloped narrow driveway beside the hotel.Take the time to line up the car to go straight through the narrow gate and you’ll be fine. Also very nice sitting area beside the restaurant. " [](https://expedia.ca/Montalcino-Hotels-Hotel-Dei-Capitani.h2520185.Hotel-Information) ![Hotel San Gregorio](//images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/9fda43a3_y.jpg) ### Hotel San Gregorio 10/10 Excellent "Super convenient location steps to the historic center. Possibly the only hotel with its own dedicated secure / covered parking. Well decorated and breakfast was great!" [](https://expedia.ca/Pienza-Hotels-Hotel-San-Gregorio.h2692135.Hotel-Information) ![SI Montalcino Hotel](//images.trvl-media.com/lodging/9000000/8670000/8662800/8662747/cba09c68_y.jpg) ### SI Montalcino Hotel 10/10 Excellent "Quiet, staff was professional and friendly, lots of parking" [](https://expedia.ca/Montalcino-Hotels-SI-Montalcino-Hotel-Restaurant.h8662747.Hotel-Information) ![Hotel Relais II Chiostro di Pienza](//images.trvl-media.com/lodging/1000000/900000/893100/893017/ef61d192_y.jpg) ### Hotel Relais II Chiostro di Pienza 10/10 Excellent "Excellent location in the heart of pienza old town, the view to the Toscana hills and valleys was unique, great experience staying in this hotel " [](https://expedia.ca/Pienza-Hotels-Hotel-Relais-II-Chiostro-Di-Pienza.h893017.Hotel-Information) ![Hotel Corsignano](//images.trvl-media.com/lodging/3000000/2530000/2525700/2525690/e0c5b2be_y.jpg) ### Hotel Corsignano 10/10 Excellent "Perfect stay" [](https://expedia.ca/Pienza-Hotels-Hotel-Corsignano.h2525690.Hotel-Information) ![Castello Banfi - Il Borgo](//images.trvl-media.com/lodging/5000000/4780000/4774100/4774015/89af6209_y.jpg) ### Castello Banfi - Il Borgo 10/10 Excellent "The setting, scenery and hotel were 5 star plus!" [](https://expedia.ca/Montalcino-Hotels-Castello-Banfi-Il-Borgo.h4774015.Hotel-Information) ![Boutique Villa Liberty - Depandance Hotel - Borgo Capitano Collection - Albergo diffuso](//images.trvl-media.com/lodging/12000000/11760000/11752200/11752153/3c5a4f24_y.jpg) ### Boutique Villa Liberty - Depandance Hotel - Borgo Capitano Collection - Albergo diffuso 10/10 Excellent "Villa Liberty is a lovely hotel. Great room, with an excellent bathroom and a garden patio. Located one block outside the Old Town (which made parking easier). Fabulous breakfast at the related restaurant in Old Town (3 minute walk). Helpful staff. " [](https://expedia.ca/San-Quirico-DOrcia-Hotels-Hotel-Villa-Del-Capitano-Art-Relais-Historic-Luxury-Capitano-Collection.h11752153.Hotel-Information) ![Rosewood Castiglion del Bosco](//images.trvl-media.com/lodging/3000000/2180000/2173600/2173539/9ace3d4a_y.jpg) ### Rosewood Castiglion del Bosco 10/10 Excellent "Beautiful property and great service. Was a little disappointed they charge double the price for wine they make in their back yard then I pay here in Montreal." 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