Title: Book the Best HISTORIC Hotels in Hillsdale in 2026 | Expedia.ca [Hillsdale Travel Guide](https://expedia.ca/Hillsdale.dx183683)[Hotels in Hillsdale](https://expedia.ca/Hillsdale-Hotels.d183683.Travel-Guide-Hotels)[Vacation Rentals in Hillsdale](https://expedia.ca/Hillsdale-Vacation-Rentals.d183683.Travel-Guide-VacationRentals)[Hillsdale Car Rentals](https://expedia.ca/Car-Rentals-In-Hillsdale.d183683.Car-Rental-Guide)[Hillsdale Vacation Packages](https://expedia.ca/Hillsdale.d183683.Destination-Travel-Guides) ![Red and Green Norway Maple Trees and Wood Fence](https://images.trvl-media.com/place/183683/4f99f7be-1e9f-40aa-ab8f-094fc6d499c2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Hillsdale, NY from CA $265 - ![](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 Hillsdale Historic Hotels Tonight [Dec 12 - Dec 13](https://www.expedia.ca/Hotel-Search?regionId=183683&startDate=2025-12-12&endDate=2025-12-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 13 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=183683&startDate=2025-12-13&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=183683&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=183683&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Hillsdale historic hotels ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (Firehouse)](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/71ef2331.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Queen Beds (Main Inn)](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/5f2e6b29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/9b7b4cbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Red Lion Inn [](https://www.expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) Stockbridge 8.8/10 Excellent (1001) "The room was very clean. The bed, linens & towels were exceptional. All of the staff were wonderful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joyce CA $195 CA $280 total includes taxes & fees Jan 12 - Jan 13, 2026 [](https://www.expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/68000000/67270000/67268600/67268558/b528caee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/68000000/67270000/67268600/67268558/bd8601b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/68000000/67270000/67268600/67268558/677d2235.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/68000000/67270000/67268600/67268558/aeb97fc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Omega special, Sunday night thru Thursday night 5 NIGHT MINIMUM, 3 miles away, [](https://www.expedia.ca/Poughkeepsie-Hotels-Private-Bed-Bath-On-Secluded-30-Acre-Farm.h67268558.Hotel-Information) Clinton Corners 8.2/10 Very good (11) "The propert my, grounds and location is just charming. Hosts were stellar and welcoming. Accomodations warm and inviting." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dawn B. CA $193 CA $265 total includes taxes & fees Dec 13 - Dec 14 [](https://www.expedia.ca/Poughkeepsie-Hotels-Private-Bed-Bath-On-Secluded-30-Acre-Farm.h67268558.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/28000000/27560000/27551700/27551652/0ab8f96e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/28000000/27560000/27551700/27551652/2fdc0476.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/28000000/27560000/27551700/27551652/ea4dc35f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/28000000/27560000/27551700/27551652/284a1f2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Kenmore Hall [](https://www.expedia.ca/Richmond-Hotels-Inn-At-Kenmore-Hall.h27551652.Hotel-Information) Richmond 10/10 Exceptional (27) "Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Margaret CA $792 CA $869 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Richmond-Hotels-Inn-At-Kenmore-Hall.h27551652.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/69000000/68780000/68773100/68773092/8e24845d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/69000000/68780000/68773100/68773092/1941c471.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/69000000/68780000/68773100/68773092/c736a539.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/69000000/68780000/68773100/68773092/f31a431f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private room on secluded 7 acres , access to entire house including patio, porch [](https://www.expedia.ca/Clinton-Corners-Hotels-Private-Room-On-Secluded-7-Acres.h68773092.Hotel-Information) Clinton Corners 8.6/10 Excellent (30) "It was just as advertised! Host was nice included fruit and coffee " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) matt w. CA $207 CA $281 total includes taxes & fees Dec 13 - Dec 14 [](https://www.expedia.ca/Clinton-Corners-Hotels-Private-Room-On-Secluded-7-Acres.h68773092.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/37000000/36250000/36245100/36245067/21b3ce2c.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/37000000/36250000/36245100/36245067/a012462e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/37000000/36250000/36245100/36245067/add10ec8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/37000000/36250000/36245100/36245067/6f907e45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### rural, serene + sophisticated space [](https://www.expedia.ca/Red-Hook-Hotels-Rural.h36245067.Hotel-Information) Red Hook 10/10 Exceptional (7) "Beautiful property with unique accommodations in the Hudson Valley" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) BRIAN PATRICK M. CA $412 CA $525 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Red-Hook-Hotels-Rural.h36245067.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/24000000/23280000/23274600/23274540/aaef5562.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/24000000/23280000/23274600/23274540/e73723b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/24000000/23280000/23274600/23274540/a9d8787c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/24000000/23280000/23274600/23274540/b8dea340.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson [](https://www.expedia.ca/Hudson-Hotels-Light-Filled-Hudson-Home-With-Designer-Sauna.h23274540.Hotel-Information) Hudson 9.8/10 Exceptional (27) "Met our son and his girls for a little getaway. Very cool house complete with lots to do! Thank you. Hope to get to experience it during the summer months sometime." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathy M. CA $844 CA $1,515 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Hudson-Hotels-Light-Filled-Hudson-Home-With-Designer-Sauna.h23274540.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=2025-12-26&endDate=2025-12-27®ionId=183683&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Hillsdale Hotel Reviews ![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "My husband and I needed a night away between the holidaze and it was perfect! Cozy, clean and warm fireplace to nurture us during a cold snap! Shelly went above and beyond to ensure that we were comfortable and in the quietest part of the hotel. We are booking our family members there" [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 10/10 Excellent "Really quiet, peaceful stay and beautiful spot for the money. Front desk staff so nice. No elevator to second floor so keep in mind if have accessibility issues/wheelchair user. Great view and gluten free menu options. Would stay again if in area. Was just passing through on way to medical appointment. " [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Holiday Inn Express Hotel & Suites Great Barrington by IHG](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG 10/10 Excellent "Great hospitality " [](https://expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "Great staff especially Katherine " [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Hotel On North](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg) ### Hotel On North 10/10 Excellent "Spacious rooms. Attentive staff. Free parking behind the hotel." [](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![Quality Inn](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg) ### Quality Inn 10/10 Excellent "clean warm room. breakfast was small but good enough to start the day. coffee was delicious. quiet which was nice and also very close to the town center with shops so that was convenient " [](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information) ![Hampton Inn & Suites Berkshires-Lenox](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822_y.jpg) ### Hampton Inn & Suites Berkshires-Lenox 10/10 Excellent "Great stay, great breakfast" [](https://expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ![Best Western Plus Berkshire Hills Inn & Suites](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387_y.jpg) ### Best Western Plus Berkshire Hills Inn & Suites 10/10 Excellent "Loved having coffee and tea 24/7" [](https://expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![St. Charles Hotel](https://images.trvl-media.com/lodging/2000000/1640000/1639400/1639318/d1c362b4_y.jpg) ### St. Charles Hotel 10/10 Excellent "It was great! We were comfortable, it was a unique place, and met expectations! The manager was great, too! Very helpful when we had questions. " [](https://expedia.ca/Hudson-Hotels-St-Charles-Hotel.h1639318.Hotel-Information) ## Frequently asked questions ### What should a history buff expect from a stay in Hillsdale? ### How many historical hotels will I find in Hillsdale? ### What are the most important historical sites and other places to visit in Hillsdale? ### What is a historic hotel like in Hillsdale? ### What is the difference between a historic hotel and a heritage hotel? ### Do historic hotels in Hillsdale have modern facilities? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - More ways to book - [Business Hotels in Albany ](https://www.expedia.ca/Albany-Hotels-Business-Hotel.0-0-d603260-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Albany ](https://www.expedia.ca/Albany-Hotels-Couples-Resorts-Hotels.0-0-d603260-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Albany ](https://www.expedia.ca/Albany-Hotels-Hotel-With-Early-Check-In.0-0-d603260-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - 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