Title: Book the Best ADVENTURE Hotels in The Berkshires in 2026 | 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 Hotels & Resorts for Couples in The Berkshires, MA from CA $123 - ![](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 Hotels & Resorts for Couples Tonight [Dec 20 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2025-12-20&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 21 - Dec 22](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2025-12-21&endDate=2025-12-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for The Berkshires adventure hotels ![Lobby](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/251da7fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/3908437c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/b38994ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/06dae0ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Element Lenox Berkshires [](https://www.expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) Lenox 9.8/10 Exceptional (13) "New hotel very nice" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) joel CA $186 CA $208 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/b4c52f47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/w4000h2033x0y0-e62570a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/36a39838.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/5e996a34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Lenox Berkshires [](https://www.expedia.ca/Lenox-Hotels-Courtyard-By-Marriott-Lenox-Berkshires.h18109146.Hotel-Information) Lenox 9.2/10 Wonderful (591) "Roomy, clean, the view is fantastic with the foliage, exactly like the photos. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mingming CA $192 CA $214 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Lenox-Hotels-Courtyard-By-Marriott-Lenox-Berkshires.h18109146.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/99000000/98310000/98305900/98305869/1de11b2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/99000000/98310000/98305900/98305869/18aa61b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/99000000/98310000/98305900/98305869/w1018h676x0y7-7345f169.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/99000000/98310000/98305900/98305869/w515h679x0y4-c96014a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor [](https://www.expedia.ca/Hancock-Hotels-1st-Floor-Mountain-View-Suite-Ski-OnOff-At-Jiminy-Fully-Redone-Decor.h98305869.Hotel-Information) Hancock 9.8/10 Exceptional (7) "Everything was wonderful…" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alyne K. CA $206 CA $401 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Hancock-Hotels-1st-Floor-Mountain-View-Suite-Ski-OnOff-At-Jiminy-Fully-Redone-Decor.h98305869.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/862ec0e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/9af2b9a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/cc4451e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/055ed8a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family Ski Getaway in the Berkshires [](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information) Great Barrington 9.4/10 Exceptional (6) CA $279 CA $410 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/104000000/103850000/103845900/103845853/3d66f0f3.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/104000000/103850000/103845900/103845853/930055e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/104000000/103850000/103845900/103845853/8250863a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/104000000/103850000/103845900/103845853/b7039a07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer [](https://www.expedia.ca/Great-Barrington-Hotels-Close-To-Tanglewood-2BR-King-Bed-Fireplace-Sleeps-6-Mountain-View-Gem.h103845853.Hotel-Information) Great Barrington CA $428 CA $533 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Great-Barrington-Hotels-Close-To-Tanglewood-2BR-King-Bed-Fireplace-Sleeps-6-Mountain-View-Gem.h103845853.Hotel-Information) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/4f2c31bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/w1424h960x16y0-bffb2a3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/b9e06e08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/6873f6f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy. Clean. Free bagel shop. 3 Fireplaces. [](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Clean-Free-Bagel-Shop-3-Fireplaces.h120045407.Hotel-Information) Great Barrington 10/10 Exceptional (1) "The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary R. CA $468 CA $806 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Clean-Free-Bagel-Shop-3-Fireplaces.h120045407.Hotel-Information) ![Individually decorated, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/50000000/49180000/49177800/49177721/c7538df3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/50000000/49180000/49177800/49177721/25529e21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/50000000/49180000/49177800/49177721/b03b8d67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/50000000/49180000/49177800/49177721/19cf619f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pilgrim Inn [](https://www.expedia.ca/Lee-Hotels-Pilgrim-Inn.h49177721.Hotel-Information) Lee 5.8/10 (332) "Was horrible. Unsafe and scarey" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sharon CA $110 CA $123 total includes taxes & fees Jan 20 - Jan 21, 2026 [](https://www.expedia.ca/Lee-Hotels-Pilgrim-Inn.h49177721.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/123000000/122980000/122978200/122978111/c5bdc83b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/123000000/122980000/122978200/122978111/w648h383x0y1-a98b9847.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/123000000/122980000/122978200/122978111/67f64adc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/123000000/122980000/122978200/122978111/a0514206_edited_9a33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hideaway Inn Mt. Snow [](https://www.expedia.ca/West-Dover-Hotels-Hideaway-Inn-Mt-Snow.h122978111.Hotel-Information) West Dover 10/10 Exceptional (3) "Really happy with our stay and the way we felt at this hideaway " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edwin CA $147 CA $162 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/West-Dover-Hotels-Hideaway-Inn-Mt-Snow.h122978111.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/50000/42300/42279/7e4b3c86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/42300/42279/fbc655dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/50000/42300/42279/414283b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/50000/42300/42279/6326a611.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Simsbury 1820 House [](https://www.expedia.ca/Hartford-Hotels-Simsbury-1820-House.h42279.Hotel-Information) Simsbury Center 9.2/10 Wonderful (1001) "Very nice room, pleasant and helpful staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Concetta CA $213 CA $269 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Hartford-Hotels-Simsbury-1820-House.h42279.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/90000000/89220000/89214100/89214004/b246ce6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/90000000/89220000/89214100/89214004/094bec8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/90000000/89220000/89214100/89214004/1a6459a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/90000000/89220000/89214100/89214004/40ae1acb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Valley Craft Ales [](https://www.expedia.ca/Wilmington-Hotels-Valley-Craft-Ales.h89214004.Hotel-Information) Wilmington 8.4/10 Very good (186) "The staff and amenities were fantastic" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew [](https://www.expedia.ca/Wilmington-Hotels-Valley-Craft-Ales.h89214004.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=2026-01-03&endDate=2026-01-04®ionId=6047665&adults=2&nearby_group=recreation&sort=RECOMMENDED&openPlayBack=true) ## Top The Berkshires Hotel Reviews ![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 "Very good" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![The Red Lion Inn](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "Old time charm and hot tub under the stars" [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![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 "This is a wonderful place to stay. The breakfast is delicious. The pool and hot tub are delightful. The staff are like family. " [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg) ### Vacation Village in the Berkshires 10/10 Excellent "Awesome for ski" [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Hotel Downstreet, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg) ### Hotel Downstreet, an Ascend Collection Hotel 10/10 Excellent "Clean room, friendly staff. " [](https://expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ![Quality Inn Great Barrington](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg) ### Quality Inn Great Barrington 10/10 Excellent "The rooms were very clean and well kept. The beds were very comfortable. The breakfast: There was no cereal or variety of breads like bagels. Yogurts were great. I do give them the benefit of the doubt on this because it was an off week, in between holidays. It was very quiet. Staff was wonderful. We will definitely be back. " [](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.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) ![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) ![Courtyard by Marriott Lenox Berkshires](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/b4c52f47_y.jpg) ### Courtyard by Marriott Lenox Berkshires 10/10 Excellent "Clean room. Very nice staff. Quiet." [](https://expedia.ca/Lenox-Hotels-Courtyard-By-Marriott-Lenox-Berkshires.h18109146.Hotel-Information) ## Frequently asked questions ### How much do hotels for couples in The Berkshires cost? ### How many hotels for couples are there in The Berkshires? ### What are the best cheap hotels for couples in The Berkshires? ### Are there any 5-star hotels for couples in The Berkshires? ### Why book your hotel for couples in The Berkshires with Expedia? ### How can I find cheap hotels for couples in The Berkshires? ### What is there to do in The Berkshires near my hotel for couples? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [3 Star Hotels in Otis ](https://www.expedia.ca/3Star-Otis-Hotels.s30-0-d6005412.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Massachusetts ](https://www.expedia.ca/Destinations-In-Massachusetts-Hotel-With-Early-Check-In.0-0-d223-thotelwithearlycheckin.Hotel-Filter-Destinations) - [Hotels with a Lazy River in Massachusetts ](https://www.expedia.ca/Destinations-In-Massachusetts-Hotels-With-A-Lazy-River.0-0-d223-tHotelswithaLazyRiver.Hotel-Filter-Destinations) - 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