Title: Book the Best HISTORIC Hotels in Pienza 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 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 Historic Hotels in Pienza - ![](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 [Nov 9 - Nov 10](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2025-11-09&endDate=2025-11-10&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 10 - Nov 11](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2025-11-10&endDate=2025-11-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2025-11-21&endDate=2025-11-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Pienza Historic Hotels ![Interior](https://images.trvl-media.com/lodging/37000000/36370000/36364900/36364803/8477e2d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/37000000/36370000/36364900/36364803/5d93306f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/37000000/36370000/36364900/36364803/9ee300f7.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/a8b308d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### "Il Focolare" Superior Apartment in Monticchiello Monticchiello 10/10 Exceptional (8) "A wonderful quiet apartment with everything you need . Comfortable bed, good a/c, good shower, well equipped kitchen, lovely host. All uphill from the car park but that’s what you expect in a hilltop village. Excellent restaurants in the village. Not far from Pienza . And a washing machine and dryer! " ![Australia](https://a.travel-assets.com/egds/marks/flags/au.svg) Linda M. CA $162 CA $195 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Pienza-Hotels-Il-Focolare-Superior-Apartment-In-Monticchiello.h36364803.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/49000000/48840000/48837200/48837118/9a24ba4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/49000000/48840000/48837200/48837118/7290fd10.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/49000000/48840000/48837200/48837118/e139d884.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/49000000/48840000/48837200/48837118/ad75fefb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The house in the village - Angelica apartment - Vald'Orcia Monticchiello 9.8/10 Exceptional (10) "Nice and comfortable house in a beautiful tiny village " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lana A. CA $145 CA $177 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Pienza-Hotels-The-House-In-The-Village-Angelica-Apartment-ValdOrcia.h48837118.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1670000/1664000/1663916/22c9fd1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1670000/1664000/1663916/6bfc0883.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/2000000/1670000/1664000/1663916/1ee50c7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room, Valley View | Bathroom](https://images.trvl-media.com/lodging/2000000/1670000/1664000/1663916/1ff7f88b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Italia Cortona Old Town 9.0/10 Wonderful (283) "Fantastic hotel in Cortona. Perfect location, extremely accommodating staff, delicious breakfast. Best place to stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) emil [](https://www.expedia.ca/Cortona-Hotels-Hotel-Italia.h1663916.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/8000000/7780000/7778900/7778813/9815a198.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/8000000/7780000/7778900/7778813/ac6c76e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/8000000/7780000/7778900/7778813/ff5236c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/8000000/7780000/7778900/7778813/1e1d576e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Antico Granaione Rapolano Terme 9.8/10 Exceptional (59) "Ottimo tutto, buon rapporto qualità/prezzo. Serre di Rapolano é una piccolissima cittadina medioevale veramente deliziosa" ![Italy](https://a.travel-assets.com/egds/marks/flags/it.svg) Massimo [](https://www.expedia.ca/Rapolano-Terme-Hotels-Antico-Granaione.h7778813.Hotel-Information) ![Single Room, 1 Single Bed, Private Bathroom, City View | View from room](https://images.trvl-media.com/lodging/24000000/23070000/23063500/23063422/6b57812f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room, Private Bathroom, City View | Bathroom](https://images.trvl-media.com/lodging/24000000/23070000/23063500/23063422/6a93c509.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/24000000/23070000/23063500/23063422/6bac2565.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Triple Room, Private Bathroom, City View | Exterior](https://images.trvl-media.com/lodging/24000000/23070000/23063500/23063422/fe6f317e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### B&B San Francesco Cortona Old Town 8.8/10 Excellent (55) "Loved our room. Owner and staff very pleasant and caring" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Barbara [](https://www.expedia.ca/Cortona-Hotels-BB-San-Francesco.h23063422.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/093ed3b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop terrace](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/36720704.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/124b8b86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/17ae36fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residenza Fabroni Montepulciano 8.8/10 Excellent (93) "We had a great stay! Beautiful on the roof top terrace!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer CA $119 CA $137 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Montepulciano-Hotels-Residenza-Fabroni.h8204306.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/49000000/48720000/48711100/48711007/9d4ea066.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/49000000/48720000/48711100/48711007/9be37908.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/49000000/48720000/48711100/48711007/bbe8b3b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![7 bedrooms, internet](https://images.trvl-media.com/lodging/49000000/48720000/48711100/48711007/2513fe04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### VILLA CHIGI - Seven Bedroom Villa, Sleeps 14 Siena CA $9,719 CA $9,719 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Buonconvento-Hotels-VILLA-CHIGI-Seven-Bedroom-Villa.h48711007.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/24000000/23280000/23275600/23275535/5ff3c1e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, bidet, towels](https://images.trvl-media.com/lodging/24000000/23280000/23275600/23275535/4589cff6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/24000000/23280000/23275600/23275535/644ef42b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/24000000/23280000/23275600/23275535/d909396a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Gelda house, relax with a view Castelnuovo dell'Abate 9.6/10 Exceptional (14) "We loved the village setting and the apartment was very comfortable and well appointed." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephen J. CA $162 CA $231 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Montalcino-Hotels-The-Gelda-House.h23275535.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/26000000/25120000/25110200/25110187/2759da14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/26000000/25120000/25110200/25110187/482cbf05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/26000000/25120000/25110200/25110187/9297b22f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/26000000/25120000/25110200/25110187/43239361.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country House in the heart of Tuscany, near Terme, free Wifi Armaiolo 10/10 Exceptional (1) "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 $145 CA $174 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Rapolano-Terme-Hotels-Country-House-In-The-Heart-Of-Tuscany.h25110187.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/41000000/40230000/40221500/40221427/ec9bd8b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/41000000/40230000/40221500/40221427/ff617fb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/41000000/40230000/40221500/40221427/cb24f428.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/41000000/40230000/40221500/40221427/30c3d6b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Exclusive Stone Tower. Casciano 9.8/10 Exceptional (7) "The tower was a perfect place for our trip to Tuscany! It had a ton of space with a full kitchen and living room. The town it is located in is fantastic. There is a small grocery store, a pizza place, and a fantastic restaurant where two people can get a delicious meal and drinks for about €30 all within walking distance. You can easily drive from the tower to Siena, Florence, Montalcino, Montepulciano, and I'm sure many other places that we didn't have time to get to. Sauro was a great host and... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael G. CA $130 CA $228 total includes taxes & fees Nov 14 - Nov 15 [](https://www.expedia.ca/Murlo-Hotels-Exclusive-Tower-In-Stone.h40221427.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=2025-11-23&endDate=2025-11-24®ionId=6023645&adults=2&specialized_stays_group_explore=historic_property&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 "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) ![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 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) ![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) ![Fonteverde Lifestyle & Thermal Retreat](//images.trvl-media.com/lodging/1000000/910000/909000/908918/f6fb188e_y.jpg) ### Fonteverde Lifestyle & Thermal Retreat 10/10 Excellent "Best resort I’ve ever stayed in! So clean, bathroom is refreshing, the many thermal pools, the views, I’ll be going back every year." [](https://expedia.ca/San-Casciano-Dei-Bagni-Hotels-Fonteverde.h908918.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 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) ![Hotel Villa Ricci](//images.trvl-media.com/lodging/3000000/2120000/2118800/2118741/f2ae49db_y.jpg) ### Hotel Villa Ricci 10/10 Excellent "We enjoyed everything about our stay except the shower was a little hinky: no shower enclosure, just a curtain." [](https://expedia.ca/Chianciano-Terme-Hotels-Hotel-Villa-Ricci.h2118741.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) ## Frequently asked questions ### What can a history buff expect from a stay in Pienza? > The historical places in Pienza are likely a big part of your travel plans. While you're in this quaint area, why not also discover all of the sights in the area? ### What's the best hotel in Pienza to learn about local history? > [House with private pool with beautiful view Val d 'Orcia](https://www.expedia.ca/Pienza-Hotels-House-With-Private-Pool-With-Beautiful-View-Val-D-Orcia.h27130089.Hotel-Information) is one of the top choices for history buffs. ### How many historically relevant hotels are there in Pienza? > In Pienza, there are 178 hotel accommodations bookable on Expedia, including 2 hotels designated as historic or close to historic sites. ### What are the top historical places and other sights to visit in Pienza? > Pienza is notable for landmarks like Palazzo Piccolomini, Historic Centre of Pienza, and Pienza Cathedral. Cultural venues include Palazzo Borgia, Artemisia Gallery, and Art Studio di Adelina Quadri. A couple of additional sights to add to your agenda are Val di Chiana and Piazza Pio II. ### What is a historic hotel like in Pienza? > A guest who chooses a historic hotel has an opportunity to stay in a place that's been recognized with an official historic designation. Historic hotels throughout the world come in all forms like castles, palaces or even pubs or old police stations. These types of hotels in Pienza often preserve original qualities such as period features or traditional architecture within the guestrooms or public spaces. ### What is the difference between a historic hotel and a heritage hotel? > These terms are similar. "Historic hotel" is more commonly used in the U.S., while you'll often hear "heritage hotel" in Asia and Europe. Historic hotels tend to focus on the architecture and building. Mainly a heritage hotel draws meaning from the place's cultural value and how it influenced the community. ### Do historic hotels in Pienza have modern facilities? > Yes, efforts are made to preserve historic facades and treasured traditions, but hotel interiors are fitted with modern conveniences and safety features. Tourists who book a stay can expect the usual amenities you'd get from a hotel such as WiFi, heating and air conditioning, and updated bathroom facilities. 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