Title: Book the Best HISTORIC Hotels in The Berkshires in 2025 | Expedia.ca [The Berkshires Travel Guide](https://expedia.ca/The-Berkshires.dx6047665)[Hotels in The Berkshires](https://expedia.ca/The-Berkshires-Hotels.d6047665.Travel-Guide-Hotels)[Vacation Rentals in The Berkshires](https://expedia.ca/The-Berkshires-Vacation-Rentals.d6047665.Travel-Guide-VacationRentals)[Flights to The Berkshires](https://expedia.ca/Cheap-Flights-To-The-Berkshires.d6047665.Travel-Guide-Flights)[The Berkshires Car Rentals](https://expedia.ca/Car-Rentals-In-The-Berkshires.d6047665.Car-Rental-Guide)[The Berkshires Vacation Packages](https://expedia.ca/The-Berkshires.d6047665.Destination-Travel-Guides) ![The Berkshires which includes flowers](https://images.trvl-media.com/place/6047665/e95ad08c-cd3f-48ea-b01c-31171bbd50b7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Photo courtesy of Berkshire Visitors Bureau # Find Historic Hotels in The Berkshires, MA - ![](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 The Berkshires Historic Hotels Tonight [Nov 15 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2025-11-15&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 16 - Nov 17](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2025-11-16&endDate=2025-11-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2025-11-21&endDate=2025-11-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2025-11-28&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top The Berkshires 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) ![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) ![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) ![Exterior](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d969459c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Red Lion Inn Stockbridge 8.8/10 Excellent (1001) "I love the ambience - historic and comfortable and excellent food. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nancy CA $216 CA $304 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/70000000/69790000/69787500/69787457/9c846f70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/70000000/69790000/69787500/69787457/w1008h683x16y0-72a8567d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/70000000/69790000/69787500/69787457/9abb62fb_edited_7b4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/70000000/69790000/69787500/69787457/2a4ba750.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn Hancock 10/10 Exceptional (23) "This property is spacious, clean and well- appointed. I would stay here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda M. CA $147 CA $331 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Hancock-Hotels-SKI-ONOFF-1BR-SUITE-1ST-FLR-SLEEPS-4-JIMINY-PEAK.h69787457.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w907h683x58y0-59aad182.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w905h683x60y0-b01f3b74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w507h683x259y0-1d5f8c7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w510h683x258y0-04b5e846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### North Getaway Cottage Williamstown 9.4/10 Exceptional (23) "The cottage was the perfect accommodations for our overnight stay in town for a funeral. Thank you Claudia. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary Alice H. CA $284 CA $624 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Williamstown-Hotels-Vacation-Getaway-Or-Remote-Workschool-Location.h60763766.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/41000000/40230000/40226600/40226569/fc1c3458.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/41000000/40230000/40226600/40226569/cf853f42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/41000000/40230000/40226600/40226569/dd5fd351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/41000000/40230000/40226600/40226569/c4a5d927.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas! Hoosick Falls 9.8/10 Exceptional (99) "Loved the location - very quiet! The house has everything you could possibly need and was very clean. It worked out perfectly for my visit to the area and I would definitely stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan T. CA $163 CA $433 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Hoosick-Falls-Hotels-Cozy-Ski-Retreat-With-New-Pet-Yard-And-Many-Upgrades-Close-To-3-Ski-Areas.h40226569.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/20000000/19820000/19812300/19812250/beddc5d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/20000000/19820000/19812300/19812250/3f9ce895.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/20000000/19820000/19812300/19812250/bee8460a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/20000000/19820000/19812300/19812250/9e5b89dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A European Country Getaway ~ 1930s Stone Cottage In Connecticut! Granby 10/10 Exceptional (94) "Beautiful local area, nicely remodeled old stone saltbox cottage. Quiet break and will revisit when back in the area.Great hosts, Thank you again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dale B. CA $210 CA $377 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/North-Granby-Hotels-A-European-Country-Getaway-1930s-Stone-Cottage-In-Connecticut.h19812250.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) ![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) ![Dining](https://images.trvl-media.com/lodging/37000000/36250000/36245100/36245067/8f88ebfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### rural, serene + sophisticated space Red Hook 10/10 Exceptional (7) "A beautifully curated barn overlooking a picturesque landscape. Gregg, the owner, really cares and wants to make sure you have everything you need. We stayed over a weekend when we were attending a wedding in the area. It was so nice to have a place to relax amidst all the festivities. The birdsong and bullfrog chorus led us to some of the soundest sleep we’ve enjoyed in a long time. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathryn CA $321 CA $502 total includes taxes & fees Nov 17 - Nov 18 [](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) ![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) ![Outdoor dining](https://images.trvl-media.com/lodging/24000000/23280000/23274600/23274540/19823f49.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) ### Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson Hudson 9.8/10 Exceptional (27) "Gorgeous house with utmost attention to detail. Sienna was so lovely and we had a wonderful time staying at the place. Highly recommend" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ellen T. CA $860 CA $1,553 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Hudson-Hotels-Light-Filled-Hudson-Home-With-Designer-Sauna.h23274540.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/52000000/51690000/51685500/51685419/1bc1a012.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/52000000/51690000/51685500/51685419/4f70f9c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/52000000/51690000/51685500/51685419/010bda9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/52000000/51690000/51685500/51685419/w1026h680x0y3-1207c37a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville Collinsville 10/10 Exceptional (61) "We had a perfect stay - the house is adorable and was just right for two of us. The river and neighborhood are great, as was the proximity to the center of town. We'll be back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Courtney N. CA $365 CA $637 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Canton-Hotels-Gorgeous-River-Views-On-Rails-To-Trails-And-Just-Steps-To-Quaint-Collinsville.h51685419.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=2025-11-29&endDate=2025-11-30®ionId=6047665&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top The Berkshires Hotel Reviews ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "Great stay!" [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "The staff were awesome! Both ladies at the front desk were so nice and accommodating. Would definitely stay there again!" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ### Hampton Inn & Suites Berkshires-Lenox 10/10 Excellent "Clean, pleasant staff and good breakfast. " [](https://expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ### Hotel On North 10/10 Excellent "The room was very clean and spacious ! The staff were very friendly and helpful - the hotel itself had a great vibe complete with hardcover books in a little coffee nook - just perfect and fun !" [](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![Holiday Inn Express Hotel & Suites Great Barrington by IHG](//images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG 10/10 Excellent "Early check in." [](https://expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ![Quality Inn](//images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg) ### Quality Inn 10/10 Excellent "The staff was amazing, so kind and accommodating. The room was clean, the beds were very comfortable. Nice breakfast options. We were in town for a concert at Mahaiwe and we didn’t use our car once we checked in… a great home base for the weekend. Will definitely be back. " [](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information) ![The Red Lion Inn](//images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "I love the ambience - historic and comfortable and excellent food. " [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Monument Mountain Motel](//images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/fa93cb94_y.jpg) ### Monument Mountain Motel 10/10 Excellent "Yes" [](https://expedia.ca/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information) ### Hotel Downstreet, an Ascend Collection Hotel 10/10 Excellent "Good value. A good place." 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