Title: Book the Best HISTORIC Hotels in Val d'Orcia in 2025 | Expedia.ca [Val d'Orcia Travel Guide](https://expedia.ca/Val-DOrcia.dx6047918)[Hotels in Val d'Orcia](https://expedia.ca/Val-DOrcia-Hotels.d6047918.Travel-Guide-Hotels)[Vacation Rentals in Val d'Orcia](https://expedia.ca/Val-DOrcia-Vacation-Rentals.d6047918.Travel-Guide-VacationRentals)[Flights to Val d'Orcia](https://expedia.ca/Cheap-Flights-To-Val-DOrcia.d6047918.Travel-Guide-Flights)[Val d'Orcia Car Rentals](https://expedia.ca/Car-Rentals-In-Val-DOrcia.d6047918.Car-Rental-Guide)[Val d'Orcia Vacation Packages](https://expedia.ca/Val-DOrcia.d6047918.Destination-Travel-Guides) ![Cathedral of Pienza featuring religious elements, a church or cathedral and heritage elements](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/208000/208193-Cathedral-Of-Pienza.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Val d'Orcia ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Val d'Orcia Historic Hotels Tonight [Oct 4 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6047918&startDate=2025-10-04&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 5 - Oct 6](https://www.expedia.ca/Hotel-Search?regionId=6047918&startDate=2025-10-05&endDate=2025-10-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6047918&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6047918&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Val d'Orcia Historic Hotels ![Breakfast, lunch, dinner served; Italian cuisine, garden views ](https://images.trvl-media.com/lodging/1000000/530000/528500/528472/2334a48c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/530000/528500/528472/c02fb06d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/530000/528500/528472/d0de7308.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 outdoor pools, free cabanas, pool umbrellas](https://images.trvl-media.com/lodging/1000000/530000/528500/528472/a69a08b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Il Falconiere - Relais e Chateaux Cortona 9.4/10 Exceptional (118) "Absolutely Amazing place / stay ! My wife and I only have raving reviews…for us it is in our Top 3 best Hotel stay ever…and we have been to some amazing Hotels before around the world. " CA $398 CA $445 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Cortona-Hotels-Relais-Il-Falconiere.h528472.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/23000000/22740000/22735400/22735381/1a8f278f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/23000000/22740000/22735400/22735381/1485528f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Minibar, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/23000000/22740000/22735400/22735381/w950h517x0y3-72b20c2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/23000000/22740000/22735400/22735381/73476eb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Ghibellino Buonconvento 8.4/10 Very good (43) "Fabulous helpful staff" CA $114 CA $129 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Buonconvento-Hotels-Hotel-Ghibellino.h22735381.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1670000/1664000/1663916/12f79b6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Italia Cortona Old Town 9.0/10 Wonderful (276) "Right in the middle of Cortona. Nice place for sure. " CA $144 CA $163 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Cortona-Hotels-Hotel-Italia.h1663916.Hotel-Information) ![2 outdoor pools, open 8:30 AM to 6:30 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/3000000/2180000/2173600/2173539/9ace3d4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; Italian cuisine](https://images.trvl-media.com/lodging/3000000/2180000/2173600/2173539/7c5ee645.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa (Stabbi) | View from room](https://images.trvl-media.com/lodging/3000000/2180000/2173600/2173539/c373f952.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; Italian cuisine](https://images.trvl-media.com/lodging/3000000/2180000/2173600/2173539/8826686a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rosewood Castiglion del Bosco Montalcino 10/10 Exceptional (66) "Definitely the best property in Tuscany.. People, food, amenities, the property itself - all perfect !" CA $2,836 CA $3,136 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Montalcino-Hotels-Rosewood-Castiglion-Del-Bosco.h2173539.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/19000000/18980000/18976500/18976420/8def11f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18980000/18976500/18976420/5d163297.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18980000/18976500/18976420/8e2d77d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18980000/18976500/18976420/26d5f3cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The House of Alice, charm and relaxation Montalcino (SI) 9.8/10 Exceptional (66) "Unbelievable ambience and beauty of the region and the house. Francesco was super helpful. " CA $262 CA $352 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Montalcino-Hotels-The-House-Of-Alice.h18976420.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/c6793766.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 (7) "Nice and comfortable house in a beautiful tiny village " CA $155 CA $187 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Pienza-Hotels-The-House-In-The-Village-Angelica-Apartment-ValdOrcia.h48837118.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) ![Fireplace, books](https://images.trvl-media.com/lodging/24000000/23280000/23275600/23275535/e3578963.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 (13) "We loved the village setting and the apartment was very comfortable and well appointed." CA $164 CA $232 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Montalcino-Hotels-The-Gelda-House.h23275535.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/34000000/33960000/33956800/33956732/da1f953b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33960000/33956800/33956732/a142d3f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33960000/33956800/33956732/cdcd98ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/34000000/33960000/33956800/33956732/35cc03f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Large double bedroom: private bathroom, private access, garden and swimming pool Radicofani 10/10 Exceptional (1) "Il nostro soggiorno è stato bellissimo. Il casale è splendido, si respira un'atmosfera d'altri tempi; la nostra camera matrimoniale era ampia e pulitissima. Anche a Novembre, la vista della campagna della Val d'Orcia che si aveva dalla camera è indimenticabile. Abbiamo fatto bene a fidarci delle foto e delle descrizioni della struttura. Grazie per la vostra calorosa accoglienza." CA $147 CA $154 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Radicofani-Hotels-Delightful-Apartment-Olivo-5-2-Places-In-Val-Dorcia-Swimming-Pool.h33956732.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34430000/34420700/34420647/506bf68f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34430000/34420700/34420647/41322e4a.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) ![TV, fireplace, books](https://images.trvl-media.com/lodging/35000000/34430000/34420700/34420647/e45bbbd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Large apartment with garden in an old farmhouse with swimming pool Radicofani 10/10 Exceptional (3) "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." CA $295 CA $301 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Radicofani-Hotels-Agriturismo-Pietreta-Apartment-Olivo-5-2-Sleeping-Accommodations.h34420647.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/36000000/35210000/35202500/35202485/52c46b77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/36000000/35210000/35202500/35202485/2ac52315.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/36000000/35210000/35202500/35202485/2cff8560.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/36000000/35210000/35202500/35202485/d1bb3909.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Romantic apartment with garden in a farmhouse with swimming pool Radicofani CA $164 CA $170 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Radicofani-Hotels-Agriturismo-Pietreta-Quercia-Suite-Suite-2-Beds.h35202485.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=2025-10-17&endDate=2025-10-18®ionId=6047918&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Val d'Orcia Hotel Reviews ![Hotel Corsignano](//images.trvl-media.com/lodging/3000000/2530000/2525700/2525690/e0c5b2be_y.jpg) ### Hotel Corsignano 10/10 Excellent "Wonderful hotel! Beautiful, very clean, staff was great, friendly and helpful. Perfect location for seeing the town and hiking to amazing views. Loved it!" [](https://expedia.ca/Pienza-Hotels-Hotel-Corsignano.h2525690.Hotel-Information) ![Castello Banfi - Il Borgo](//images.trvl-media.com/lodging/5000000/4780000/4774100/4774015/89af6209_y.jpg) ### Castello Banfi - Il Borgo 10/10 Excellent "What a property! The drive in is stunning. Amazing greeting. Easy parking within a gated area. The check-in was first class. We were given a tour of the property which is incredible. The rooms are incredible. Then we experienced a wine tasting that we won't forget. The Banfi wines are amazing. Then we experienced arguably our favourite dining experience at the Michelin Star restaurant on the property. What a property! What a team!! We are already discussing our return. " [](https://expedia.ca/Montalcino-Hotels-Castello-Banfi-Il-Borgo.h4774015.Hotel-Information) ![SI Montalcino Hotel](//images.trvl-media.com/lodging/9000000/8670000/8662800/8662747/cba09c68_y.jpg) ### SI Montalcino Hotel 10/10 Excellent "The staff were exceptional! So warm, welcoming and helpful. The property is lovely. The rooms had lovely wine glasses and bottle opener, which is perfect for wine country! Breakfast was great! a Fun place to stay" [](https://expedia.ca/Montalcino-Hotels-SI-Montalcino-Hotel-Restaurant.h8662747.Hotel-Information) ![Boutique Villa Liberty - Depandance Hotel - Borgo Capitano Collection - Albergo diffuso](//images.trvl-media.com/lodging/12000000/11760000/11752200/11752153/3c5a4f24_y.jpg) ### Boutique Villa Liberty - Depandance Hotel - Borgo Capitano Collection - Albergo diffuso 10/10 Excellent "Villa Liberty is a lovely hotel. Great room, with an excellent bathroom and a garden patio. Located one block outside the Old Town (which made parking easier). Fabulous breakfast at the related restaurant in Old Town (3 minute walk). Helpful staff. " [](https://expedia.ca/San-Quirico-DOrcia-Hotels-Hotel-Villa-Del-Capitano-Art-Relais-Historic-Luxury-Capitano-Collection.h11752153.Hotel-Information) ![Hotel Dei Capitani](//images.trvl-media.com/lodging/3000000/2530000/2520200/2520185/156cc4b3_y.jpg) ### Hotel Dei Capitani 10/10 Excellent "This was a fantastic place to stay while visiting Montalcino. Spectacular views from our room and from the breakfast area and pool deck. Staff was very hospitable, and the breakfast buffet was really good. Mimosa’s restaurant recommendations were on point😎. I picked this place somewhat randomly for me and my dad and did not regret it. Walking distance to great restaurants and gelato. Rooms are not elaborate, but you’re not there to stay in your room. A couple of suggestions: - if you put this place into Apple Maps or Google Maps, IT WILL SEND YOU UP A GRAVEL AGRICULTURAL ROAD WITH 20% GRADE, the Strada Communale Del Canaliccio. OMG, my heart was in my throat driving up this and we narrowly avoided an accident. Instead, ask Maps app to take you to Via Pietro Strozzi, then to the hotel. We made it safely, but there was some stress!! - there is very little permanent parking at the hotel. Drive there, drop your stuff, and they will give you a parking pass and directions to parking. - this may not be the place for those with severely limited mobility. The cobblestone roads are pretty steep. - if you need suggestions for wineries, there are so many, but Col D’Orcia won’t let you down. Book ahead.🍷" [](https://expedia.ca/Montalcino-Hotels-Hotel-Dei-Capitani.h2520185.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.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 "I don't know where to begin the hotel is in center of everything nice underground parking garage and the staff couldn't been any friendly, helpful and caring The reception staffs their where excelent if We are coming back to pienza staying there 💯 percent thanks you so much " [](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 "The pictures do not do it justice - stunning setting and view, very nice hotel, very kind attentive staff. Would definitely recommend. " [](https://expedia.ca/Pienza-Hotels-Hotel-Relais-II-Chiostro-Di-Pienza.h893017.Hotel-Information) ![Rosewood Castiglion del Bosco](//images.trvl-media.com/lodging/3000000/2180000/2173600/2173539/9ace3d4a_y.jpg) ### Rosewood Castiglion del Bosco 10/10 Excellent "Beautiful property and great service. Was a little disappointed they charge double the price for wine they make in their back yard then I pay here in Montreal." 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