Title: The Best Pienza Chalets from $228 | Expedia.com [Pienza Travel Guide](https://expedia.com/Pienza.dx6023645)[Hotels in Pienza](https://expedia.com/Pienza-Hotels.d6023645.Travel-Guide-Hotels)[Vacation Rentals in Pienza](https://expedia.com/Pienza-Vacation-Rentals.d6023645.Travel-Guide-VacationRentals)[Flights to Pienza](https://expedia.com/Cheap-Flights-To-Pienza.d6023645.Travel-Guide-Flights)[Things to do in Pienza](https://expedia.com/Things-To-Do-In-Pienza.d6023645.Travel-Guide-Activities)[Car Rentals in Pienza](https://expedia.com/Car-Rentals-In-Pienza.d6023645.Car-Rental-Guide)[Pienza Vacation Packages](https://expedia.com/Pienza.d6023645.Destination-Travel-Guides) ![Pienza showing a small town or village, a monument and heritage architecture](https://images.trvl-media.com/place/6023645/9d678ea5-9752-4000-8f7c-af307fb65e61.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6023645/9d678ea5-9752-4000-8f7c-af307fb65e61.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=6023645&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=6023645&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=6023645&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=6023645&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Pienza chalets ![Exterior](https://images.trvl-media.com/lodging/107000000/106530000/106529000/106528941/7d66933c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player](https://images.trvl-media.com/lodging/107000000/106530000/106529000/106528941/b286febc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/107000000/106530000/106529000/106528941/933ef644.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106530000/106529000/106528941/74694acb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Trequanda [](https://www.expedia.com/Trequanda-Hotels-Elegant-Chalet-On-The-Ground-Floor-Of-Approximately-80-M2-Consisting-Of-A-Large-Living-Room-With-Fireplace.h106528941.Hotel-Information) $198 nightly $242 total Mar 11 - Mar 12 Total with taxes and fees [](https://www.expedia.com/Trequanda-Hotels-Elegant-Chalet-On-The-Ground-Floor-Of-Approximately-80-M2-Consisting-Of-A-Large-Living-Room-With-Fireplace.h106528941.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/126000000/125210000/125202500/125202480/a1e12d05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Internet, bed sheets](https://images.trvl-media.com/lodging/126000000/125210000/125202500/125202480/55ec26d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books](https://images.trvl-media.com/lodging/126000000/125210000/125202500/125202480/f168054e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/126000000/125210000/125202500/125202480/9e15ae12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Trequanda [](https://www.expedia.com/Trequanda-Hotels-Chalet-Cigno-Apartment-In-Tuscany.h125202480.Hotel-Information) $224 nightly $228 total Apr 7 - Apr 8 Total with taxes and fees [](https://www.expedia.com/Trequanda-Hotels-Chalet-Cigno-Apartment-In-Tuscany.h125202480.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/126000000/125210000/125202000/125201955/ab017dc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, internet](https://images.trvl-media.com/lodging/126000000/125210000/125202000/125201955/9628580b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/126000000/125210000/125202000/125201955/eaae26ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/126000000/125210000/125202000/125201955/687e4e18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Trequanda [](https://www.expedia.com/Trequanda-Hotels-Apartment-Azzurro-Cignella-Resort-Tuscany.h125201955.Hotel-Information) $307 nightly $311 total Mar 9 - Mar 10 Total with taxes and fees [](https://www.expedia.com/Trequanda-Hotels-Apartment-Azzurro-Cignella-Resort-Tuscany.h125201955.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/126000000/125210000/125202500/125202434/f36c6729.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/126000000/125210000/125202500/125202434/d16a1de0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, coffee/tea maker, highchair, cookware/dishes/utensils](https://images.trvl-media.com/lodging/126000000/125210000/125202500/125202434/9aabae14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/126000000/125210000/125202500/125202434/648ca878.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Siena [](https://www.expedia.com/Trequanda-Hotels-Apartment-Rosmarino-Cignella-Resort-Tuscany.h125202434.Hotel-Information) $290 nightly $293 total Apr 7 - Apr 8 Total with taxes and fees [](https://www.expedia.com/Trequanda-Hotels-Apartment-Rosmarino-Cignella-Resort-Tuscany.h125202434.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/92000000/91130000/91124000/91123913/aa9b8534.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/92000000/91130000/91124000/91123913/25cdcd40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91130000/91124000/91123913/b290e00d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91130000/91124000/91123913/41493c86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Trequanda [](https://www.expedia.com/Trequanda-Hotels-Chalet-Villa-Falco-With-Shared-Pool.h91123913.Hotel-Information) $697 nightly $701 total Mar 9 - Mar 10 Total with taxes and fees [](https://www.expedia.com/Trequanda-Hotels-Chalet-Villa-Falco-With-Shared-Pool.h91123913.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/92000000/91130000/91124000/91123905/c2891cd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, stereo](https://images.trvl-media.com/lodging/92000000/91130000/91124000/91123905/8ba5a29e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/92000000/91130000/91124000/91123905/9ee8907a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/92000000/91130000/91124000/91123905/0894d2f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Trequanda [](https://www.expedia.com/Trequanda-Hotels-Chalet-Azzurro-With-Mountain-View.h91123905.Hotel-Information) $604 nightly $608 total Mar 9 - Mar 10 Total with taxes and fees [](https://www.expedia.com/Trequanda-Hotels-Chalet-Azzurro-With-Mountain-View.h91123905.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/92000000/91190000/91188500/91188496/2093877e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/92000000/91190000/91188500/91188496/845d47cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/92000000/91190000/91188500/91188496/60a69234.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/92000000/91190000/91188500/91188496/89d7065f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Trequanda [](https://www.expedia.com/Trequanda-Hotels-Chalet-Cigno-With-Shared-Pool-Wi-Fi.h91188496.Hotel-Information) $511 nightly $511 total Mar 9 - Mar 10 Total with taxes and fees [](https://www.expedia.com/Trequanda-Hotels-Chalet-Cigno-With-Shared-Pool-Wi-Fi.h91188496.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/126000000/125210000/125202700/125202607/281ff3ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/126000000/125210000/125202700/125202607/c0c66e87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/126000000/125210000/125202700/125202607/2e17254a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/126000000/125210000/125202700/125202607/a36b7806.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Trequanda [](https://www.expedia.com/Trequanda-Hotels-Villa-Basilico-Cignella-Resort-Chalet-In-Tuscany.h125202607.Hotel-Information) $287 nightly $290 total Mar 9 - Mar 10 Total with taxes and fees [](https://www.expedia.com/Trequanda-Hotels-Villa-Basilico-Cignella-Resort-Chalet-In-Tuscany.h125202607.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.com/Hotel-Search?startDate=2026-03-22&endDate=2026-03-23®ionId=6023645&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=AA_SPRING_PROMO_6023645) ## Find vacation rentals that suit your style Villas [](https://www.expedia.com/Hotel-Search?destination=Pienza%2C+Tuscany%2C+Italy®ionId=6023645&latLong=43.076766%2C11.678764&adults=2&startDate=2026-06-05&d1=2026-06-05&endDate=2026-06-08&d2=2026-06-08&lodging=VILLA) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Pienza%2C+Tuscany%2C+Italy®ionId=6023645&latLong=43.076766%2C11.678764&adults=2&startDate=2026-06-05&d1=2026-06-05&endDate=2026-06-08&d2=2026-06-08&lodging=VACATION_HOME) Apartments [](https://www.expedia.com/Hotel-Search?destination=Pienza%2C+Tuscany%2C+Italy®ionId=6023645&latLong=43.076766%2C11.678764&adults=2&startDate=2026-06-05&d1=2026-06-05&endDate=2026-06-08&d2=2026-06-08&lodging=APARTMENT) Residences [](https://www.expedia.com/Hotel-Search?destination=Pienza%2C+Tuscany%2C+Italy®ionId=6023645&latLong=43.076766%2C11.678764&adults=2&startDate=2026-06-05&d1=2026-06-05&endDate=2026-06-08&d2=2026-06-08&lodging=RESIDENCE) Aparthotels [](https://www.expedia.com/Hotel-Search?destination=Pienza%2C+Tuscany%2C+Italy®ionId=6023645&latLong=43.076766%2C11.678764&adults=2&startDate=2026-06-05&d1=2026-06-05&endDate=2026-06-08&d2=2026-06-08&lodging=APART_HOTEL) Cottages [](https://www.expedia.com/Hotel-Search?destination=Pienza%2C+Tuscany%2C+Italy®ionId=6023645&latLong=43.076766%2C11.678764&adults=2&startDate=2026-06-05&d1=2026-06-05&endDate=2026-06-08&d2=2026-06-08&lodging=COTTAGE) Condos [](https://www.expedia.com/Hotel-Search?destination=Pienza%2C+Tuscany%2C+Italy®ionId=6023645&latLong=43.076766%2C11.678764&adults=2&startDate=2026-06-05&d1=2026-06-05&endDate=2026-06-08&d2=2026-06-08&lodging=CONDO) Chalets [](https://www.expedia.com/Hotel-Search?destination=Pienza%2C+Tuscany%2C+Italy®ionId=6023645&latLong=43.076766%2C11.678764&adults=2&startDate=2026-06-05&d1=2026-06-05&endDate=2026-06-08&d2=2026-06-08&lodging=CHALET) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FPienza-Chalets.d6023645-aaChalets.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FPienza-Chalets.d6023645-aaChalets.Travel-Guide-Accommodation) ## Top Pienza Hotel Reviews ![Hotel Santa Caterina](https://images.trvl-media.com/lodging/3000000/2550000/2540800/2540753/3b315dde_y.jpg) ### Hotel Santa Caterina 10/10 Excellent "Very beautiful hotel by the city wall,friendly staff and a good breakfast." [](https://expedia.com/Siena-Hotels-Hotel-Santa-Caterina.h2540753.Hotel-Information) ![Fonteverde Lifestyle & Thermal Retreat](https://images.trvl-media.com/lodging/1000000/910000/909000/908918/11ad8811_y.jpg) ### Fonteverde Lifestyle & Thermal Retreat 10/10 Excellent "Great place! Excellent service by everyone we encountered. " [](https://expedia.com/San-Casciano-Dei-Bagni-Hotels-Fonteverde.h908918.Hotel-Information) ![Hotel Relais II Chiostro di Pienza](https://images.trvl-media.com/lodging/1000000/900000/893100/893017/45dfbbfc_y.jpg) ### Hotel Relais II Chiostro di Pienza 10/10 Excellent "A little tired, extremely clean, with an amazing staff" [](https://expedia.com/Pienza-Hotels-Hotel-Relais-II-Chiostro-Di-Pienza.h893017.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 "The best in Siena." [](https://expedia.com/Siena-Hotels-Hotel-Certosa-Di-Maggiano.h528470.Hotel-Information) ![Relais Villa Grazianella - UNA Esperienze](https://images.trvl-media.com/lodging/5000000/4320000/4310500/4310479/cd1e0f87_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.com/Montepulciano-Hotels-Relais-Villa-Grazianella-UNA-Esperienze.h4310479.Hotel-Information) ![Hotel Corsignano](https://images.trvl-media.com/lodging/3000000/2530000/2525700/2525690/ba2de8ee_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.com/Pienza-Hotels-Hotel-Corsignano.h2525690.Hotel-Information) ![Affitacamere Maria Gabriella](https://images.trvl-media.com/lodging/23000000/22940000/22938800/22938763/020483c6_y.jpg) ### Affitacamere Maria Gabriella 10/10 Excellent "This property has a lovely view, great garden, attentive staff with good breakfast. Stayed in the cottage and the patio was very sunny and relaxing. " [](https://expedia.com/Pienza-Hotels-Affitacamere-Maria-Gabriella.h22938763.Hotel-Information) ![Villa di Piazzano - Small Luxury Hotel of the World](https://images.trvl-media.com/lodging/1000000/980000/972000/971985/c358cc6c_y.jpg) ### Villa di Piazzano - Small Luxury Hotel of the World 10/10 Excellent "Room was wonderful, bathroom spacious and well appointed. Staff amazing and so friendly " [](https://expedia.com/Cortona-Hotels-Villa-Di-Piazzano-Small-Luxury-Hotel-Of-The-World.h971985.Hotel-Information) ![Precise Tale Poggio Alla Sala](https://images.trvl-media.com/lodging/91000000/90890000/90888700/90888666/33c1dfc6_y.jpg) ### Precise Tale Poggio Alla Sala 10/10 Excellent "Fantastic hotel in an incredible setting. Staff were extremely helpful, attentive and understanding. The perfect location for a relaxing break and a centre for exploring Tuscany" [](https://expedia.com/Montepulciano-Hotels-Precise-Tale-Poggio-Alla-Sala.h90888666.Hotel-Information) ## Find out more about Pienza ## Pienza Chalets information | Number of reviews | | | ----------------- | ---------- | | Accommodation | 11 Chalets | | Lowest Price | $228 | | Highest Price | $701 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - More ways to book - [Hotels near Piazza Pio II ](https://www.expedia.com/Piazza-Pio-II-Hotels.0-l553248621533000907-0.Travel-Guide-Filter-Hotels) - [Hotels near Pienza Cathedral ](https://www.expedia.com/Pienza-Cathedral-Hotels.0-l6105122-0.Travel-Guide-Filter-Hotels) - [Hotels near Palazzo Vescovile ](https://www.expedia.com/Palazzo-Vescovile-Hotels.0-l553248621533000905-0.Travel-Guide-Filter-Hotels) - [Hotels near RI Crea RE ](https://www.expedia.com/RI-Crea-RE-Hotels.0-l553248621562145314-0.Travel-Guide-Filter-Hotels) - 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