Title: TOP Winery Hotels in Pienza for 2025 | Expedia.co.uk [Pienza Travel Guide](https://expedia.co.uk/Pienza.dx6023645)[Hotels in Pienza](https://expedia.co.uk/Pienza-Hotels.d6023645.Travel-Guide-Hotels)[Holiday Rentals in Pienza](https://expedia.co.uk/Pienza-Holiday-Rentals.d6023645.Travel-Guide-HolidayRentals)[Flights to Pienza](https://expedia.co.uk/Cheap-Flights-To-Pienza.d6023645.Travel-Guide-Flights)[Things to do in Pienza](https://expedia.co.uk/Things-To-Do-In-Pienza.d6023645.Travel-Guide-Activities)[Pienza Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Pienza.d6023645.Car-Hire-Guide)[Pienza Holidays](https://expedia.co.uk/Pienza.d6023645.Holidays-City-Breaks) ![Pienza which includes a small town or village and heritage architecture 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) # Search Winery Hotels in Pienza ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) ![](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 [14 Oct - 15 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=6023645&startDate=2025-10-14&endDate=2025-10-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [15 Oct - 16 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=6023645&startDate=2025-10-15&endDate=2025-10-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [17 Oct - 19 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=6023645&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [24 Oct - 26 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=6023645&startDate=2025-10-24&endDate=2025-10-26&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 | Egyptian cotton sheets, premium bedding, down duvets](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) ![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 (117) "Great countryside stay" £187 includes taxes & fees 27 Oct - 28 Oct [](https://www.expedia.co.uk/Pienza-Hotels-Tenuta-Santo-Pietro.h2750235.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) ![Garden](https://images.trvl-media.com/lodging/115000000/114240000/114237800/114237760/36f43408.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) ![Suite | 1 bedroom, free WiFi](https://images.trvl-media.com/lodging/115000000/114240000/114237800/114237760/296fa814.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sant'Anna in Camprena Agriturismo Pienza 10/10 Exceptional (5) "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. " £169 includes taxes & fees 14 Oct - 15 Oct [](https://www.expedia.co.uk/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) ![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) ![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 Pienza 9.4/10 Exceptional (130) "Such friendly staff, loved Pienza and the property was such a good location! " £104 includes taxes & fees 4 Nov - 5 Nov [](https://www.expedia.co.uk/Pienza-Hotels-Hotel-San-Gregorio.h2692135.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, pool loungers](https://images.trvl-media.com/lodging/1000000/900000/893100/893017/06a2992b.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) ![View from property](https://images.trvl-media.com/lodging/1000000/900000/893100/893017/537f8719.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Relais II Chiostro di Pienza Pienza 8.8/10 Excellent (620) "The perfect location. Gorgeous property. Excellent breakfast. " [](https://www.expedia.co.uk/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) ![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) ![Garden](https://images.trvl-media.com/lodging/23000000/22950000/22946200/22946136/b2818bfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Agriturismo Il Macchione Pienza 9.6/10 Exceptional (54) "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." [](https://www.expedia.co.uk/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) ![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) ![Junior Suite | 1 bedroom, premium bedding, down duvets, minibar](https://images.trvl-media.com/lodging/3000000/2530000/2525700/2525690/777a1195.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 Pienza 9.4/10 Exceptional (321) "Enjoyed the hotel. Great location, quality breakfast and rooms." £106 includes taxes & fees 12 Nov - 13 Nov [](https://www.expedia.co.uk/Pienza-Hotels-Hotel-Corsignano.h2525690.Hotel-Information) ![Camera Superior, vista città, primo piano senza ascensore | 1 bedroom, laptop workspace, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/115000000/114870000/114863300/114863278/c5b2d059.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Camera Superior, vista città, primo piano senza ascensore | 1 bedroom, laptop workspace, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/115000000/114870000/114863300/114863278/e4f61737.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。" £79 includes taxes & fees 2 Nov - 3 Nov [](https://www.expedia.co.uk/Pienza-Hotels-TuscanyLettings-StudioRoom.h114863278.Hotel-Information) ![Casa Gioia, vista città, 2 piano senza ascensore | Private kitchen | Fridge, microwave, stovetop, electric kettle](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 | 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 Olivieri, vista città, 1 piano senza ascensore | Bathroom | Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/116000000/115080000/115077100/115077012/w1068h1606x0y0-b99034fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Casa Olivieri, vista città, 1 piano senza ascensore | Private kitchen | Fridge, microwave, stovetop, electric kettle](https://images.trvl-media.com/lodging/116000000/115080000/115077100/115077012/f32e69c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casa Gioia - Casa Olivieri Pienza £87 includes taxes & fees 2 Nov - 3 Nov [](https://www.expedia.co.uk/Pienza-Hotels-Casa-Gioia-Casa-Olivieri.h115077012.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/fc49cce8.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) ### Hotel Rutiliano Centro Benessere Pienza 8.6/10 Excellent (7) "Its a little hotel with a great host!! " [](https://www.expedia.co.uk/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) ![Terrace/patio](https://images.trvl-media.com/lodging/6000000/5070000/5065600/5065554/b03f172d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Studio Ground Floor | 1 bedroom, Frette Italian sheets, premium bedding, desk](https://images.trvl-media.com/lodging/6000000/5070000/5065600/5065554/01e65d9d.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 (54) "Quaint hotel in the heart of Pienza. Comfortable and close to all amenities. " [](https://www.expedia.co.uk/Pienza-Hotels-Rossellino.h5065554.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.co.uk/Hotel-Search?startDate=2025-10-27&endDate=2025-10-28®ionId=6023645&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Pienza Hotel Reviews ![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.co.uk/Cortona-Hotels-Villa-Di-Piazzano-Small-Luxury-Hotel-Of-The-World.h971985.Hotel-Information) ![Hotel Corsignano](//images.trvl-media.com/lodging/3000000/2530000/2525700/2525690/e0c5b2be_y.jpg) ### Hotel Corsignano 10/10 Excellent "Enjoyed the hotel. Great location, quality breakfast and rooms." [](https://expedia.co.uk/Pienza-Hotels-Hotel-Corsignano.h2525690.Hotel-Information) ![Hotel San Gregorio](//images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/9fda43a3_y.jpg) ### Hotel San Gregorio 10/10 Excellent "Excellent property! Very elegant and the service was wonderful. The breakfast was also excellent. The location could not be any better - the entry to the old town is just across from the hotel. Wish we could have stayed longer." [](https://expedia.co.uk/Pienza-Hotels-Hotel-San-Gregorio.h2692135.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.co.uk/Pienza-Hotels-Tenuta-Santo-Pietro.h2750235.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 perfect location. Gorgeous property. Excellent breakfast. " [](https://expedia.co.uk/Pienza-Hotels-Hotel-Relais-II-Chiostro-Di-Pienza.h893017.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.co.uk/Siena-Hotels-Hotel-Certosa-Di-Maggiano.h528470.Hotel-Information) ![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.co.uk/Asciano-Hotels-Precise-House-Montaperti-Siena.h1110834.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.co.uk/Montalcino-Hotels-Castello-Di-Velona-Resort-The-Leading-Hotels-Of-The-World.h1037832.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.co.uk/Chianciano-Terme-Hotels-Grand-Hotel-Terme.h1289175.Hotel-Information) ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - Other - More ways to book - [4 Star Hotels in Montisi](https://www.expedia.co.uk/4Star-Montisi-Hotels.s40-0-d3000027304.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Val d'Orcia](https://www.expedia.co.uk/4Star-Val-DOrcia-Hotels.s40-0-d6047918.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Montepulciano](https://www.expedia.co.uk/5Star-Montepulciano-Hotels.s50-0-d601351.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Val d'Orcia](https://www.expedia.co.uk/5Star-Val-DOrcia-Hotels.s50-0-d6047918.Travel-Guide-Filter-Hotels) - [Spa Hotels in Bagno Vignoni](https://www.expedia.co.uk/Bagno-Vignoni-Hotels-Spa-Hotels.0-0-d6142908-tSpaHotels.Travel-Guide-Filter-Hotels) - [Bagno Vignoni Hotels](https://www.expedia.co.uk/Bagno-Vignoni-Hotels.d6142908.Travel-Guide-Hotels) - [Castelmuzio Hotels](https://www.expedia.co.uk/Castelmuzio-Hotels.d6285810.Travel-Guide-Hotels) - 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