Title: Book the Best Pienza WINERY Hotels in 2025 | Expedia.ca [Pienza Travel Guide](https://expedia.ca/Pienza.dx6023645)[Hotels in Pienza](https://expedia.ca/Pienza-Hotels.d6023645.Travel-Guide-Hotels)[Vacation Rentals in Pienza](https://expedia.ca/Pienza-Vacation-Rentals.d6023645.Travel-Guide-VacationRentals)[Flights to Pienza](https://expedia.ca/Cheap-Flights-To-Pienza.d6023645.Travel-Guide-Flights)[Things to do in Pienza](https://expedia.ca/Things-To-Do-In-Pienza.d6023645.Travel-Guide-Activities)[Pienza Car Rentals](https://expedia.ca/Car-Rentals-In-Pienza.d6023645.Car-Rental-Guide)[Pienza Vacation Packages](https://expedia.ca/Pienza.d6023645.Destination-Travel-Guides) ![Pienza which includes heritage architecture and a small town or village as well as a small group of people](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/157000/157948-Pienza.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Pienza from CA $130 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Pienza Winery Hotels Tonight [Sep 25 - Sep 26](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2025-09-25&endDate=2025-09-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 26 - Sep 27](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2025-09-26&endDate=2025-09-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2025-09-26&endDate=2025-09-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Pienza Winery Hotels ## Our top choices for Pienza hotels with winery ![Exterior](https://images.trvl-media.com/lodging/112000000/111490000/111484800/111484787/5a7bf3ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, Vineyard View, Executive Level | View from room](https://images.trvl-media.com/lodging/112000000/111490000/111484800/111484787/b57e1382.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Winery](https://images.trvl-media.com/lodging/112000000/111490000/111484800/111484787/464ad77a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111490000/111484800/111484787/401cae24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Podere Montale Winery Seggiano 9.2/10 Wonderful (5) "We stayed at the Winery and the views were amazing! The sunsets were the best from our entire trip! The staff was always helpful and willing to doing whatever they could to make your visit remarkable. We would definitely recommend staying here!" CA $201 CA $221 total includes taxes & fees Oct 24 - Oct 25 [](https://www.expedia.ca/Seggiano-Hotels-Podere-Montale-Winery.h111484787.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2530000/2524000/2523911/ec6cd8ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Apartment, 2 Bedrooms, Kitchen, Garden Area](https://images.trvl-media.com/lodging/3000000/2530000/2524000/2523911/d0f89602.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room](https://images.trvl-media.com/lodging/3000000/2530000/2524000/2523911/30b6036d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Apartment, 2 Bedrooms, Kitchen, Garden Area](https://images.trvl-media.com/lodging/3000000/2530000/2524000/2523911/4977666a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### AgriHotel Villa Ambra Montepulciano 9.2/10 Wonderful (163) "Great location, easy parking, nice breakfast and friendly staff. " CA $112 CA $130 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Montepulciano-Hotels-Villa-Ambra.h2523911.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) ![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) ![Lounge](https://images.trvl-media.com/lodging/3000000/2760000/2750300/2750235/a71dc3ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tenuta Santo Pietro Pienza 9.6/10 Exceptional (115) "The hotel is amazing! The localization is great, 5 minutes from Pienza. The view is stunning and the restaurant is great! Betina is a very nice host and welcomed us very well." CA $290 CA $326 total includes taxes & fees Oct 25 - Oct 26 [](https://www.expedia.ca/Pienza-Hotels-Tenuta-Santo-Pietro.h2750235.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2540000/2533300/2533253/23323ff6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Apartment | Living area](https://images.trvl-media.com/lodging/3000000/2540000/2533300/2533253/d8a6a342.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Double Room](https://images.trvl-media.com/lodging/3000000/2540000/2533300/2533253/8b52e51c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served, Italian cuisine, garden views ](https://images.trvl-media.com/lodging/3000000/2540000/2533300/2533253/b7ea94d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cortona Resort - Le Terre Dei Cavalieri Cortona 9.8/10 Exceptional (71) "I will be back again! Lovely place. Restaurant is excellent too!" CA $211 CA $240 total includes taxes & fees Sep 26 - Sep 27 [](https://www.expedia.ca/Cortona-Hotels-Cortona-Resort-Le-Terre-Dei-Cavalieri.h2533253.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) ![Garden](https://images.trvl-media.com/lodging/23000000/22950000/22946200/22946136/b2818bfa.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) ![Dishwasher, coffee/tea maker, electric kettle, cookware/dishes/utensils](https://images.trvl-media.com/lodging/23000000/22950000/22946200/22946136/a19596f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Agriturismo Il Macchione Pienza 9.6/10 Exceptional (53) "This was a wonderful spot to stay a short distance outside of town in a very quiet peaceful area. The room was large and comfortable, and the breakfast was excellent. Everyone there was very kind and friendly." CA $191 CA $217 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Pienza-Hotels-Agriturismo-Il-Macchione.h22946136.Hotel-Information) ![Interior detail](https://images.trvl-media.com/lodging/115000000/114240000/114237800/114237760/f1f44d26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite](https://images.trvl-media.com/lodging/115000000/114240000/114237800/114237760/296fa814.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114240000/114237800/114237760/643505d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden view](https://images.trvl-media.com/lodging/115000000/114240000/114237800/114237760/c783fcd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sant'Anna in Camprena Agriturismo Pienza 10/10 Exceptional (3) "We had a memorable stay at Sant'Anna Agriturismo. This is a truly unique property. We got to all access to the monastery including the Church, the lemon garden, the large dining halls. It is a very special place. Our hosts were very welcoming, they did everything to help us settle in. I would highly recommend the property to anyone who is visiting Tuscany. " CA $282 CA $317 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Pienza-Hotels-SantAnna-In-Camprena-Agriturismo.h114237760.Hotel-Information) ![Breakfast, lunch, dinner served; local cuisine ](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/9fda43a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fountain](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/2d2d56ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast buffet](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/cd7670ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/4a89a1fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel San Gregorio Pienza 9.4/10 Exceptional (127) "Such friendly staff, loved Pienza and the property was such a good location! " CA $243 CA $277 total includes taxes & fees Oct 25 - Oct 26 [](https://www.expedia.ca/Pienza-Hotels-Hotel-San-Gregorio.h2692135.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) ![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) ![Interior entrance](https://images.trvl-media.com/lodging/3000000/2530000/2525700/2525690/7c006ed3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite](https://images.trvl-media.com/lodging/3000000/2530000/2525700/2525690/777a1195.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Corsignano Pienza 9.4/10 Exceptional (319) "The staff is wonderful and the hotel is beautiful, perfectly situated near Pienza center. We loved it, felt very comfortable, and will be back!" CA $276 CA $314 total includes taxes & fees Oct 25 - Oct 26 [](https://www.expedia.ca/Pienza-Hotels-Hotel-Corsignano.h2525690.Hotel-Information) ![Suite Bernardo, Panoramica al terzo piano senza ascensore](https://images.trvl-media.com/lodging/113000000/112330000/112327700/112327681/8ce91a76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite Bernardo, Panoramica al terzo piano senza ascensore](https://images.trvl-media.com/lodging/113000000/112330000/112327700/112327681/f758a3cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite Silvio al secondo piano senza ascensore](https://images.trvl-media.com/lodging/113000000/112330000/112327700/112327681/05bb40d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite Silvio al secondo piano senza ascensore | Living area](https://images.trvl-media.com/lodging/113000000/112330000/112327700/112327681/21ae19f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### PienzaLettings Suites Pienza 10/10 Exceptional (1) "Fantastic room in the city center, close to everything in Pienza" CA $128 CA $147 total includes taxes & fees Oct 24 - Oct 25 [](https://www.expedia.ca/Pienza-Hotels-PienzaLettings-Suites.h112327681.Hotel-Information) ![Camera Superior, vista città, primo piano senza ascensore](https://images.trvl-media.com/lodging/115000000/114870000/114863300/114863278/c5b2d059.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Monolocale Exclusive, vista città, secondo piano senza ascensore | Living area](https://images.trvl-media.com/lodging/115000000/114870000/114863300/114863278/6be6d8fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/115000000/114870000/114863300/114863278/cc713796.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Monolocale Exclusive, vista città, secondo piano senza ascensore | Private kitchen](https://images.trvl-media.com/lodging/115000000/114870000/114863300/114863278/4381c139.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### TuscanyLettings Studio&Room Pienza 10/10 Exceptional (1) "メイン通りの好立地。 客室は豪華でエレガント。 ウェルカムキットも良く、アメニティも良好。 次回も必ず利用したい。 スタッフの方、いろいろありがとうございました。" CA $149 CA $170 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Pienza-Hotels-TuscanyLettings-StudioRoom.h114863278.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=2025-10-09&endDate=2025-10-10®ionId=6023645&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Pienza Hotel Reviews ![Precise House Montaperti Siena](//images.trvl-media.com/lodging/2000000/1120000/1110900/1110834/2f957dff_y.jpg) ### Precise House Montaperti Siena 8/10 Good "Lovely staff. Misleading advertisement regarding queen bed and single bed in the apartment. There are 2 single beds and a pull out couch." [](https://expedia.ca/Asciano-Hotels-Precise-House-Montaperti-Siena.h1110834.Hotel-Information) ![Hotel Certosa Di Maggiano](//images.trvl-media.com/lodging/1000000/530000/528500/528470/4c3dd1ab_y.jpg) ### Hotel Certosa Di Maggiano 10/10 Excellent "Entire Team was phenomenal. Paula at Front Desk was beyond phenomenal. Thank you! " [](https://expedia.ca/Siena-Hotels-Hotel-Certosa-Di-Maggiano.h528470.Hotel-Information) ![Tenuta Santo Pietro](//images.trvl-media.com/lodging/3000000/2760000/2750300/2750235/4fa44438_y.jpg) ### Tenuta Santo Pietro 10/10 Excellent "We had the most incredible stay at Tenuta Santo Pietro in Toscana! From the moment we arrived, we felt completely at home. Bertina, the manager, is truly the heartbeat of this place. She’s funny, full of energy, literally skipping around even after a long day, and never forgets a thing. Her attention to detail is impeccable, and she made us feel like old friends — chatting and laughing with her was one of the best parts of our trip. The rest of the staff is amazing too. Teresa and Micaela were always there, warm and attentive, making sure we were comfortable and well-fed. The estate itself is stunning, decorated in rustic Tuscan style, with a garden supplying fresh veggies for incredible homemade dishes — the pasta and ribollita soup were unforgettable. Their olive oil and wine, both produced on-site, are absolute highlights: the olive oil is the best we’ve ever had, and the wine is smooth, high-quality, and headache-free. Our room was beautiful, the bed super comfortable, and the shower had the strongest water pressure we’ve ever experienced. We rented e-bikes and explored Strada Querciassale — the views were breathtaking. The pool was perfect to cool off, and the entire property is impeccably maintained. Tenuta Santo Pietro is a rare gem where you feel pampered yet completely at home. Bertina and her team made our stay unforgettable — we’ll definitely be back!" [](https://expedia.ca/Pienza-Hotels-Tenuta-Santo-Pietro.h2750235.Hotel-Information) ![Hotel Corsignano](//images.trvl-media.com/lodging/3000000/2530000/2525700/2525690/e0c5b2be_y.jpg) ### Hotel Corsignano 10/10 Excellent "Beautiful rooms and excellent breakfast. The staff " [](https://expedia.ca/Pienza-Hotels-Hotel-Corsignano.h2525690.Hotel-Information) ![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 "Me and my wife stayed there for our honeymoon. We had an exceptional time. The service was exceptional. The pools and amenities were very nice. Great! Breakfast was just free. Located close to montel Chino and many great wineries. Specifically, we really enjoyed the wine tasting. The entire staff were great but here were some standouts , We were helped by Kristian who made us feel extremely welcomed and Morris who performed our wine tasting and he was an exceptional. Strong recommendation, great value." [](https://expedia.ca/Montalcino-Hotels-Castello-Di-Velona-Resort-The-Leading-Hotels-Of-The-World.h1037832.Hotel-Information) ![Villa di Piazzano - Small Luxury Hotel of the World](//images.trvl-media.com/lodging/1000000/980000/972000/971985/473f66a9_y.jpg) ### Villa di Piazzano - Small Luxury Hotel of the World 10/10 Excellent "If you like a peaceful quiet getaway this is the place!" [](https://expedia.ca/Cortona-Hotels-Villa-Di-Piazzano-Small-Luxury-Hotel-Of-The-World.h971985.Hotel-Information) ![Hotel San Michele](//images.trvl-media.com/lodging/1000000/990000/984500/984435/cd5b1ca8_y.jpg) ### Hotel San Michele 10/10 Excellent "Very friendly and helpful staff. Nice rooms" [](https://expedia.ca/Cortona-Hotels-Hotel-San-Michele.h984435.Hotel-Information) ![Hotel San Gregorio](//images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/9fda43a3_y.jpg) ### Hotel San Gregorio 10/10 Excellent "I don't know where to begin the hotel is in center of everything nice underground parking garage and the staff couldn't been any friendly, helpful and caring The reception staffs their where excelent if We are coming back to pienza staying there 💯 percent thanks you so much " [](https://expedia.ca/Pienza-Hotels-Hotel-San-Gregorio.h2692135.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 "The pictures do not do it justice - stunning setting and view, very nice hotel, very kind attentive staff. Would definitely recommend. 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