Title: Book the Best HISTORIC Hotels in Pienza 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) ![](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__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 Historic Hotels Tonight [Apr 4 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2026-04-04&endDate=2026-04-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Apr 5 - Apr 6](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2026-04-05&endDate=2026-04-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2026-04-10&endDate=2026-04-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2026-04-17&endDate=2026-04-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Pienza historic hotels ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/37000000/36370000/36364900/36364803/6e91d9be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/37000000/36370000/36364900/36364803/824ca8c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/37000000/36370000/36364900/36364803/49bf4281.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/37000000/36370000/36364900/36364803/64e505a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### "Il Focolare" Superior Apartment in Monticchiello [](https://www.expedia.ca/Pienza-Hotels-Il-Focolare-Superior-Apartment-In-Monticchiello.h36364803.Hotel-Information) Monticchiello 10/10 Exceptional (8 reviews) "An wonderfully presented apartment in a beautiful town away from the tourist areas but close enough with a short drive. It’s a beautiful town and the apartment is a welcome retreat when you have enjoyed enough of the Tuscan sun. It’s clear the owner has attention to detail and that made our stay even better! " ![Australia](https://a.travel-assets.com/egds/marks/flags/au.svg) Dan CA $153 CA $188 total includes taxes & fees Apr 6 - Apr 7 [](https://www.expedia.ca/Pienza-Hotels-Il-Focolare-Superior-Apartment-In-Monticchiello.h36364803.Hotel-Information) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/49000000/48840000/48837200/48837118/e139d884.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/49000000/48840000/48837200/48837118/da956da6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/49000000/48840000/48837200/48837118/9a24ba4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/49000000/48840000/48837200/48837118/aaa84aae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The house in the village - Angelica apartment - Vald'Orcia [](https://www.expedia.ca/Pienza-Hotels-The-House-In-The-Village-Angelica-Apartment-ValdOrcia.h48837118.Hotel-Information) Monticchiello 10/10 Exceptional (11 reviews) "Marco was great to work with, was easily available for any of our questions and the stay was wonderful. The apartment is in a great location and had all we needed for our stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa B. CA $162 CA $194 total includes taxes & fees Apr 11 - Apr 12 [](https://www.expedia.ca/Pienza-Hotels-The-House-In-The-Village-Angelica-Apartment-ValdOrcia.h48837118.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/26000000/25120000/25110200/25110187/530c4574.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV, fireplace, books](https://images.trvl-media.com/lodging/26000000/25120000/25110200/25110187/cb239dcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/26000000/25120000/25110200/25110187/e67b20cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/26000000/25120000/25110200/25110187/2759da14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country House in the heart of Tuscany, near Terme, free Wifi [](https://www.expedia.ca/Rapolano-Terme-Hotels-Country-House-In-The-Heart-Of-Tuscany.h25110187.Hotel-Information) Armaiolo 10/10 Exceptional (1 review) "Abbiamo passato 3 gg veramente perfetti in questo appartamento davvero molto carino e spazioso in cui non mancava nulla,con una camera decisamente spaziosa e un soggiorno con cucina altrettanto grandi e in perfetto stile rustico rimesso a nuovo. E poi che dire dello spazio esterno e soprattutto della gentilezza e cortesia del proprietario Alessio,che ha fatto di tutto x farci stare al meglio,con un ottimo barbecue compreso!Ci torneremo di sicuro,posto assolutamente consigliato!!! Manuel e Paola." ![Italy](https://a.travel-assets.com/egds/marks/flags/it.svg) Manuel D. CA $143 CA $172 total includes taxes & fees Apr 7 - Apr 8 [](https://www.expedia.ca/Rapolano-Terme-Hotels-Country-House-In-The-Heart-Of-Tuscany.h25110187.Hotel-Information) ![55-inch Smart TV with satellite channels, TV, Netflix](https://images.trvl-media.com/lodging/4000000/3550000/3547700/3547611/e99138c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite](https://images.trvl-media.com/lodging/4000000/3550000/3547700/3547611/e1f273e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite | Bathroom](https://images.trvl-media.com/lodging/4000000/3550000/3547700/3547611/6b1f2619.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite](https://images.trvl-media.com/lodging/4000000/3550000/3547700/3547611/6770de59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Palazzo Carletti [](https://www.expedia.ca/Montepulciano-Hotels-Palazzo-Carletti.h3547611.Hotel-Information) Montepulciano 9.8/10 Exceptional (241 reviews) "Beautiful hotel in a beautiful little town. Staff was very nice and helpful; breakfast was excellent and check in communication was top notch." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Margaret CA $343 CA $383 total includes taxes & fees Apr 30 - May 1 [](https://www.expedia.ca/Montepulciano-Hotels-Palazzo-Carletti.h3547611.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34430000/34420700/34420647/ceb18968.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34430000/34420700/34420647/8bade8be.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/35000000/34430000/34420700/34420647/9c3bf6b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34430000/34420700/34420647/3248f664.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Large apartment with garden in an old farmhouse with swimming pool [](https://www.expedia.ca/Radicofani-Hotels-Agriturismo-Pietreta-Apartment-Olivo-5-2-Sleeping-Accommodations.h34420647.Hotel-Information) Radicofani 10/10 Exceptional (3 reviews) "The appartement was nice and large with a lovely atmosphere. The children enjoyed the pool a lot. The house's location was amazing with a lovely view over the Tuscan hills." ![Netherlands](https://a.travel-assets.com/egds/marks/flags/nl.svg) Ellen V. CA $321 CA $328 total includes taxes & fees Apr 6 - Apr 7 [](https://www.expedia.ca/Radicofani-Hotels-Agriturismo-Pietreta-Apartment-Olivo-5-2-Sleeping-Accommodations.h34420647.Hotel-Information) ![1 bedroom, WiFi, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/37000000/36360000/36359700/36359627/054b2390.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/37000000/36360000/36359700/36359627/f3230669.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/37000000/36360000/36359700/36359627/55dd0445.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/37000000/36360000/36359700/36359627/8d911531.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### MDQ Events - A natural oasis on the Via Francigena [](https://www.expedia.ca/Castiglione-DOrcia-Hotels-MDQ-Events-A-Natural-Oasis-On-The-Via-Francigena.h36359627.Hotel-Information) catiglione d'orcia CA $135 CA $185 total includes taxes & fees Apr 6 - Apr 7 [](https://www.expedia.ca/Castiglione-DOrcia-Hotels-MDQ-Events-A-Natural-Oasis-On-The-Via-Francigena.h36359627.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/d05582b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/ff9693c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/a8ccbf55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/d6476b51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Il Poggio dell'Eremita [](https://www.expedia.ca/Sinalunga-Hotels-Il-Poggio-Delleremita.h27448054.Hotel-Information) Sinalunga 10/10 Exceptional (59 reviews) "Fantastic place! Great location. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Paul Q. CA $217 CA $249 total includes taxes & fees Apr 15 - Apr 16 [](https://www.expedia.ca/Sinalunga-Hotels-Il-Poggio-Delleremita.h27448054.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/124b8b86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/1def40b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/a1afa9f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/12afb28e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residenza Fabroni [](https://www.expedia.ca/Montepulciano-Hotels-Residenza-Fabroni.h8204306.Hotel-Information) Montepulciano 8.8/10 Excellent (96 reviews) "gorgeous historical property, very attentive host, great location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah CA $110 CA $128 total includes taxes & fees Apr 7 - Apr 8 [](https://www.expedia.ca/Montepulciano-Hotels-Residenza-Fabroni.h8204306.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/38000000/37600000/37593900/37593856/8e612be1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/38000000/37600000/37593900/37593856/a9225886.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/38000000/37600000/37593900/37593856/13407098.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/38000000/37600000/37593900/37593856/90-72cb5332.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Eva's house awaits you! [](https://www.expedia.ca/Castel-Viscardo-Hotels-Evas-House-Awaits-You.h37593856.Hotel-Information) Monterubiaglio 10/10 Exceptional (2 reviews) "L'appartement est très grand (rez-de-chaussée d'une maison) et aménagé avec bcp de goût. Tout etait fournis à l'arrivée : linges de lit, serviettes de toilette, liquide vaisselle, éponge et torchons. L'accueil des propriétaires etaient chaleureux et leurs conseils bienvenus. Chien, chat, tortues nous ont réservés un acceuil amical. Le jardin est très grand, idéal lorsqu'on a des enfants. La piscine est un avantage non négligeable au vu des températures très élevées. Les villages villes... ![France](https://a.travel-assets.com/egds/marks/flags/fr.svg) Stéphanie D. CA $185 CA $230 total includes taxes & fees Apr 6 - Apr 7 [](https://www.expedia.ca/Castel-Viscardo-Hotels-Evas-House-Awaits-You.h37593856.Hotel-Information) ![Lunch and dinner served, local cuisine](https://images.trvl-media.com/lodging/22000000/21340000/21339500/21339462/98406b43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch and dinner served, local cuisine](https://images.trvl-media.com/lodging/22000000/21340000/21339500/21339462/13e470bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/22000000/21340000/21339500/21339462/a8ce016d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/22000000/21340000/21339500/21339462/521d6cbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castello di Gargonza [](https://www.expedia.ca/Monte-San-Savino-Hotels-Castello-Di-Gargonza.h21339462.Hotel-Information) Monte San Savino 9.2/10 Wonderful (40 reviews) "Beautiful area and friendly staff. We stayed here several years ago and were so excited to return." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $347 CA $388 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Monte-San-Savino-Hotels-Castello-Di-Gargonza.h21339462.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=2026-04-18&endDate=2026-04-19®ionId=6023645&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Pienza Hotel Reviews ![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 "Beautiful " [](https://expedia.ca/Pienza-Hotels-Hotel-Relais-II-Chiostro-Di-Pienza.h893017.Hotel-Information) ![Hotel San Gregorio](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/0e5f89fd_y.jpg) ### Hotel San Gregorio 10/10 Excellent "Room was large and very clean. Bed was king sized and comfortable. Check-in was easy with underground parking for a nominal fee. Hotel is right outside downtown area, making it super walkable. Breakfast was great with many options. " [](https://expedia.ca/Pienza-Hotels-Hotel-San-Gregorio.h2692135.Hotel-Information) ![Hotel Corsignano](https://images.trvl-media.com/lodging/3000000/2530000/2525700/2525690/ba2de8ee_y.jpg) ### Hotel Corsignano 10/10 Excellent "The heat in the room and bath were not working. Fortunately there were extra blankets ! " [](https://expedia.ca/Pienza-Hotels-Hotel-Corsignano.h2525690.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 "Absolutely breathtaking property. The staff was extremely welcoming and helpful. Truly such a beautiful experience. Highly recommend to anyone " [](https://expedia.ca/Montepulciano-Hotels-Relais-Villa-Grazianella-UNA-Esperienze.h4310479.Hotel-Information) ![Hotel Santa Caterina](https://images.trvl-media.com/lodging/3000000/2550000/2540800/2540753/6057be8a_y.jpg) ### Hotel Santa Caterina 10/10 Excellent "Very beautiful hotel by the city wall,friendly staff and a good breakfast." [](https://expedia.ca/Siena-Hotels-Hotel-Santa-Caterina.h2540753.Hotel-Information) ![Fonteverde Lifestyle & Thermal Retreat](https://images.trvl-media.com/lodging/1000000/910000/909000/908918/f6fb188e_y.jpg) ### Fonteverde Lifestyle & Thermal Retreat 10/10 Excellent "Great place! Excellent service by everyone we encountered. " [](https://expedia.ca/San-Casciano-Dei-Bagni-Hotels-Fonteverde.h908918.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.ca/Cortona-Hotels-Villa-Di-Piazzano-Small-Luxury-Hotel-Of-The-World.h971985.Hotel-Information) ![Tenuta Santo Pietro](https://images.trvl-media.com/lodging/3000000/2760000/2750300/2750235/77df39f9_y.jpg) ### Tenuta Santo Pietro 6/10 Okay "We had to buy a bottle of wine before they would give us 2 wine glasses so we could sit outside to enjoy the view! Expecting a little more for the rate. " [](https://expedia.ca/Pienza-Hotels-Tenuta-Santo-Pietro.h2750235.Hotel-Information) ## Frequently asked questions ### What can a history buff expect from a stay in Pienza? ### What's the best hotel in Pienza to learn about local history? ### How many historically relevant hotels are there in Pienza? ### What are the top historical places and other sights to visit in Pienza? ### What is a historic hotel like in Pienza? ### What is the difference between a historic hotel and a heritage hotel? ### Do historic hotels in Pienza have modern facilities? ## 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) - 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