Title: Book the Best Pienza WINERY Hotels in 2026 | 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 showing a monument, a square or plaza and heritage architecture](https://images.trvl-media.com/place/6023645/9d678ea5-9752-4000-8f7c-af307fb65e61.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Pienza from CA $131 - ![](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 Pienza Winery Hotels Tonight [Dec 14 - Dec 15](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2025-12-14&endDate=2025-12-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 15 - Dec 16](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2025-12-15&endDate=2025-12-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Pienza hotels with winery ![Outdoor pool](https://images.trvl-media.com/lodging/23000000/22950000/22946200/22946136/44c52963.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) ![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) ![Reception](https://images.trvl-media.com/lodging/23000000/22950000/22946200/22946136/4cc1ef4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Agriturismo Il Macchione [](https://www.expedia.ca/Pienza-Hotels-Agriturismo-Il-Macchione.h22946136.Hotel-Information) Pienza 9.6/10 Exceptional (56) "The owners and staff are hospitable .and accommodating very warm people " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) aileen CA $218 CA $247 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Pienza-Hotels-Agriturismo-Il-Macchione.h22946136.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 | Private kitchen](https://images.trvl-media.com/lodging/115000000/114870000/114863300/114863278/4381c139.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) ### TuscanyLettings Studio&Room [](https://www.expedia.ca/Pienza-Hotels-TuscanyLettings-StudioRoom.h114863278.Hotel-Information) 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。" ![Japan](https://a.travel-assets.com/egds/marks/flags/jp.svg) keita CA $131 CA $150 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Pienza-Hotels-TuscanyLettings-StudioRoom.h114863278.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 | Terrace/patio](https://images.trvl-media.com/lodging/113000000/112330000/112327700/112327681/44d465f3.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) ### PienzaLettings Suites [](https://www.expedia.ca/Pienza-Hotels-PienzaLettings-Suites.h112327681.Hotel-Information) Pienza 10/10 Exceptional (1) "Fantastic room in the city center, close to everything in Pienza" ![Norway](https://a.travel-assets.com/egds/marks/flags/no.svg) Tom CA $113 CA $131 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Pienza-Hotels-PienzaLettings-Suites.h112327681.Hotel-Information) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/900000/893100/893017/ef61d192.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 9:00 AM to 7:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/900000/893100/893017/06a2992b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/1000000/900000/893100/893017/e5a8fbb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/1000000/900000/893100/893017/6ed54e03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Relais II Chiostro di Pienza [](https://www.expedia.ca/Pienza-Hotels-Hotel-Relais-II-Chiostro-Di-Pienza.h893017.Hotel-Information) Pienza 8.8/10 Excellent (630) "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 " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pedro CA $118 CA $139 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Pienza-Hotels-Hotel-Relais-II-Chiostro-Di-Pienza.h893017.Hotel-Information) ![Casa Gioia, vista città, 2 piano senza ascensore | Private kitchen](https://images.trvl-media.com/lodging/116000000/115080000/115077100/115077012/w1006h678x18y0-09d3b1e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Casa Olivieri, vista città, 1 piano senza ascensore | Private kitchen](https://images.trvl-media.com/lodging/116000000/115080000/115077100/115077012/f32e69c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Casa Olivieri, vista città, 1 piano senza ascensore | Bathroom](https://images.trvl-media.com/lodging/116000000/115080000/115077100/115077012/w1068h1606x0y0-b99034fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115080000/115077100/115077012/w1068h1589x0y0-ab9335e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casa Gioia - Casa Olivieri [](https://www.expedia.ca/Pienza-Hotels-Casa-Gioia-Casa-Olivieri.h115077012.Hotel-Information) Pienza CA $116 CA $135 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Pienza-Hotels-Casa-Gioia-Casa-Olivieri.h115077012.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) ![Junior Suite](https://images.trvl-media.com/lodging/3000000/2530000/2525700/2525690/777a1195.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) ### Hotel Corsignano [](https://www.expedia.ca/Pienza-Hotels-Hotel-Corsignano.h2525690.Hotel-Information) Pienza 9.4/10 Exceptional (330) "Enjoyed the hotel. Great location, quality breakfast and rooms." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph CA $239 CA $273 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Pienza-Hotels-Hotel-Corsignano.h2525690.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) ![Front of property](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/882d4e56.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) ![Fountain](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/2d2d56ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel San Gregorio [](https://www.expedia.ca/Pienza-Hotels-Hotel-San-Gregorio.h2692135.Hotel-Information) Pienza 9.4/10 Exceptional (134) "Such friendly staff, loved Pienza and the property was such a good location! " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Bethan CA $284 CA $322 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Pienza-Hotels-Hotel-San-Gregorio.h2692135.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/24000000/23550000/23541400/23541302/9a31e69a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/24000000/23550000/23541400/23541302/f1566451.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/24000000/23550000/23541400/23541302/ea723126.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/24000000/23550000/23541400/23541302/f69d0e12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Rutiliano Centro Benessere [](https://www.expedia.ca/Pienza-Hotels-Hotel-Rutiliano-Centro-Benessere.h23541302.Hotel-Information) Pienza 8.6/10 Excellent (7) "Its a little hotel with a great host!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Valerie [](https://www.expedia.ca/Pienza-Hotels-Hotel-Rutiliano-Centro-Benessere.h23541302.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/6000000/5070000/5065600/5065554/32ded4fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/6000000/5070000/5065600/5065554/98d42f53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Studio Ground Floor](https://images.trvl-media.com/lodging/6000000/5070000/5065600/5065554/01e65d9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/6000000/5070000/5065600/5065554/b03f172d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rossellino [](https://www.expedia.ca/Pienza-Hotels-Rossellino.h5065554.Hotel-Information) Pienza 8.6/10 Excellent (56) "Quaint hotel in the heart of Pienza. Comfortable and close to all amenities. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Debbie CA $179 CA $203 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Pienza-Hotels-Rossellino.h5065554.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/104000000/103770000/103767200/103767196/064b57ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/104000000/103770000/103767200/103767196/00edf663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/104000000/103770000/103767200/103767196/da5c0984.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103770000/103767200/103767196/24acb438.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Suite Gioconda - Podere Casa Rossa in Pienza [](https://www.expedia.ca/Pienza-Hotels-Vrbo-Property.h103767196.Hotel-Information) Pienza 10/10 Exceptional (4) "Comfortable, clean and the hosts are over the top welcoming! Walking distance to Pienza with gorgeous views. Loved staying here and hope to come back someday! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Doug H. CA $260 CA $349 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Pienza-Hotels-Vrbo-Property.h103767196.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=2025-12-28&endDate=2025-12-29®ionId=6023645&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Pienza Hotel Reviews ![Abbadia Sicille Relais](https://images.trvl-media.com/lodging/11000000/10660000/10653000/10652908/80de574a_y.jpg) ### Abbadia Sicille Relais 10/10 Excellent "Room was beyond expectations. Helpful staff and overall great experience. " [](https://expedia.ca/Trequanda-Hotels-Abbadia-Sicille.h10652908.Hotel-Information) ![Relais Villa Grazianella - UNA Esperienze](https://images.trvl-media.com/lodging/5000000/4320000/4310500/4310479/8b3fbbcc_y.jpg) ### Relais Villa Grazianella - UNA Esperienze 10/10 Excellent "Everything was perfect. Warm welcome, comfortable and spacious rooms, great breakfast. The staff was very kind and friendly. I also recommend the wine tasting experience. Highly recommended!" [](https://expedia.ca/Montepulciano-Hotels-Relais-Villa-Grazianella-UNA-Esperienze.h4310479.Hotel-Information) ![Albergo San Biagio](https://images.trvl-media.com/lodging/4000000/3230000/3224200/3224141/c85acee6_y.jpg) ### Albergo San Biagio 10/10 Excellent "gorgeous spot below the town, what an incredible view from the balcony " [](https://expedia.ca/Montepulciano-Hotels-Albergo-San-Biagio.h3224141.Hotel-Information) ![Hotel Certosa Di Maggiano](https://images.trvl-media.com/lodging/1000000/530000/528500/528470/edea64a5_y.jpg) ### Hotel Certosa Di Maggiano 10/10 Excellent "La habitación muy amplia, teníamos armario vestidor, sala, habitación amplia y un gran baño. Excelente la atención del personal. El lugar mágico maravilloso de epoca" [](https://expedia.ca/Siena-Hotels-Hotel-Certosa-Di-Maggiano.h528470.Hotel-Information) ![Hotel Corsignano](https://images.trvl-media.com/lodging/3000000/2530000/2525700/2525690/e0c5b2be_y.jpg) ### Hotel Corsignano 10/10 Excellent "Wonderful stay. Very welcoming staff and check in was quick and simple. Very convenient as parking provided. Room was spacious especially bathroom with great bathtub Breakfast was perfect" [](https://expedia.ca/Pienza-Hotels-Hotel-Corsignano.h2525690.Hotel-Information) ![Rosewood Castiglion del Bosco](https://images.trvl-media.com/lodging/3000000/2180000/2173600/2173539/9ace3d4a_y.jpg) ### Rosewood Castiglion del Bosco 10/10 Excellent "Wonderful stay " [](https://expedia.ca/Montalcino-Hotels-Rosewood-Castiglion-Del-Bosco.h2173539.Hotel-Information) ![Hotel Santa Caterina](https://images.trvl-media.com/lodging/3000000/2550000/2540800/2540753/3b315dde_y.jpg) ### Hotel Santa Caterina 10/10 Excellent "Amazing staff, great food and an even better view from the garden. " [](https://expedia.ca/Siena-Hotels-Hotel-Santa-Caterina.h2540753.Hotel-Information) ![Castello di Velona Resort Thermal SPA & Winery](https://images.trvl-media.com/lodging/2000000/1040000/1037900/1037832/87359911_y.jpg) ### Castello di Velona Resort Thermal SPA & Winery 10/10 Excellent "The property was exquisite. The view spectacular and the staff top notch. The indoor and outdoor thermal pools and sauna made our stay very relaxing. The buffet breakfast was amazing." [](https://expedia.ca/Montalcino-Hotels-Castello-Di-Velona-Resort-The-Leading-Hotels-Of-The-World.h1037832.Hotel-Information) ![Hotel Relais II Chiostro di Pienza](https://images.trvl-media.com/lodging/1000000/900000/893100/893017/ef61d192_y.jpg) ### Hotel Relais II Chiostro di Pienza 10/10 Excellent "The room was beautiful and very clean. Breakfast staff was very kind." [](https://expedia.ca/Pienza-Hotels-Hotel-Relais-II-Chiostro-Di-Pienza.h893017.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [4 Star Hotels in Montepulciano ](https://www.expedia.ca/4Star-Montepulciano-Hotels.s40-0-d601351.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Val d'Orcia ](https://www.expedia.ca/4Star-Val-DOrcia-Hotels.s40-0-d6047918.Travel-Guide-Filter-Hotels) - [Farmstay in Bagno Vignoni ](https://www.expedia.ca/Bagno-Vignoni-Agritourism.d6142908-aaAgritourism.Travel-Guide-Accommodation) - [Bagno Vignoni Hotels ](https://www.expedia.ca/Bagno-Vignoni-Hotels.d6142908.Travel-Guide-Hotels) - [Castelmuzio Hotels ](https://www.expedia.ca/Castelmuzio-Hotels.d6285810.Travel-Guide-Hotels) - [Hotels near Dome of Montepulciano ](https://www.expedia.ca/Dome-Of-Montepulciano-Hotels.0-l553248621532500181-0.Travel-Guide-Filter-Hotels) - [Montefollonico Hotels ](https://www.expedia.ca/Montefollonico-Hotels.d6285797.Travel-Guide-Hotels) - 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