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 $138 ![](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 [Oct 30 - Oct 31](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2025-10-30&endDate=2025-10-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 31 - Nov 1](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2025-10-31&endDate=2025-11-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6023645&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=6023645&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Pienza 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](https://images.trvl-media.com/lodging/3000000/2760000/2750300/2750235/42a0569c.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) ![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 (118) "Great countryside stay" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Josh CA $320 CA $359 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Pienza-Hotels-Tenuta-Santo-Pietro.h2750235.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) ![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) ![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) ### Hotel Relais II Chiostro di Pienza Pienza 8.8/10 Excellent (626) "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 $140 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Pienza-Hotels-Hotel-Relais-II-Chiostro-Di-Pienza.h893017.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) ![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) ![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) ![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 Pienza 9.6/10 Exceptional (55) "Beautiful grounds , close to town, charming room…:: we would definitely go back for a longer stay" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Patrician CA $219 CA $248 total includes taxes & fees Nov 14 - Nov 15 [](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) ![Junior Suite](https://images.trvl-media.com/lodging/3000000/2530000/2525700/2525690/777a1195.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) "Enjoyed the hotel. Great location, quality breakfast and rooms." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph CA $194 CA $224 total includes taxes & fees Nov 16 - Nov 17 [](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 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 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 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" ![Norway](https://a.travel-assets.com/egds/marks/flags/no.svg) Tom CA $120 CA $138 total includes taxes & fees Nov 30 - Dec 1 [](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) ![Camera Superior, vista città, primo piano senza ascensore](https://images.trvl-media.com/lodging/115000000/114870000/114863300/114863278/e4f61737.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。" ![Japan](https://a.travel-assets.com/egds/marks/flags/jp.svg) keita CA $131 CA $151 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Pienza-Hotels-TuscanyLettings-StudioRoom.h114863278.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 | 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 Olivieri, vista città, 1 piano senza ascensore | Living area](https://images.trvl-media.com/lodging/116000000/115080000/115077100/115077012/f6c24b45_edited_9b06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casa Gioia - Casa Olivieri Pienza CA $156 CA $179 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Pienza-Hotels-Casa-Gioia-Casa-Olivieri.h115077012.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) ![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) ### Hotel San Gregorio Pienza 9.4/10 Exceptional (131) "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 $200 CA $230 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Pienza-Hotels-Hotel-San-Gregorio.h2692135.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) ![Terrace/patio](https://images.trvl-media.com/lodging/6000000/5070000/5065600/5065554/b03f172d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/6000000/5070000/5065600/5065554/f0f2460a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rossellino Pienza 8.6/10 Excellent (55) "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 $219 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Pienza-Hotels-Rossellino.h5065554.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) ![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) ![Interior detail](https://images.trvl-media.com/lodging/24000000/23550000/23541400/23541302/ea723126.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/24000000/23550000/23541400/23541302/fc49cce8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Rutiliano Centro Benessere 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 CA $292 CA $328 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Pienza-Hotels-Hotel-Rutiliano-Centro-Benessere.h23541302.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=2025-11-13&endDate=2025-11-14®ionId=6023645&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Pienza 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 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) ![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) ![Albergo San Biagio](//images.trvl-media.com/lodging/4000000/3230000/3224200/3224141/c85acee6_y.jpg) ### Albergo San Biagio 10/10 Excellent "Great service we loved our stay" [](https://expedia.ca/Montepulciano-Hotels-Albergo-San-Biagio.h3224141.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) ![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 "This is a classic luxury hotel. I can't imagine the amount of time and energy it takes to upkeep this property. But they somehow manage to maintain a spotless, manicured and warm environment. The room was quite large and rich in design. The restaurant and the staff who work there are excellent. I was here for some mother/daughter time and we loved making this our base to visit the surrounding towns. Timeless elegance!" [](https://expedia.ca/Cortona-Hotels-Villa-Di-Piazzano-Small-Luxury-Hotel-Of-The-World.h971985.Hotel-Information) ![Tenuta Santo Pietro](//images.trvl-media.com/lodging/3000000/2760000/2750300/2750235/4fa44438_y.jpg) ### Tenuta Santo Pietro 10/10 Excellent "Great countryside stay" [](https://expedia.ca/Pienza-Hotels-Tenuta-Santo-Pietro.h2750235.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 "A wonderfully peaceful hotel in the middle of Tuscany. Amazing views. Great staff - friendly, professional and very helpful & accommodating. " [](https://expedia.ca/Siena-Hotels-Hotel-Certosa-Di-Maggiano.h528470.Hotel-Information) ![Grand Hotel Terme](//images.trvl-media.com/lodging/2000000/1290000/1289200/1289175/3fd53b10_y.jpg) ### Grand Hotel Terme 6/10 Okay "Old but maintained well. Quiet and easy" [](https://expedia.ca/Chianciano-Terme-Hotels-Grand-Hotel-Terme.h1289175.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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