Title: Great Barrington Chalets from CA $98 | Expedia.ca [Great Barrington Travel Guide](https://expedia.ca/Great-Barrington.dx110336)[Hotels in Great Barrington](https://expedia.ca/Great-Barrington-Hotels.d110336.Travel-Guide-Hotels)[Vacation Rentals in Great Barrington](https://expedia.ca/Great-Barrington-Vacation-Rentals.d110336.Travel-Guide-VacationRentals)[Flights to Great Barrington](https://expedia.ca/Cheap-Flights-To-Great-Barrington.d110336.Travel-Guide-Flights)[Great Barrington Car Rentals](https://expedia.ca/Car-Rentals-In-Great-Barrington.d110336.Car-Rental-Guide)[Great Barrington Vacation Packages](https://expedia.ca/Great-Barrington.d110336.Destination-Travel-Guides) ![Great Barrington which includes signage and night scenes](https://images.trvl-media.com/place/110336/4c3d827f-8ba1-4754-a7a1-6fe14b81f0f7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Chalets in Great Barrington from CA $98 - ![](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 prices for these dates Next weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=110336&startDate=2025-12-12&endDate=2025-12-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=110336&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=110336&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=110336&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Great Barrington Chalets No exact matches found, but these alternatives could be just right ## Recommended hotels in Great Barrington ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/be126a14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/11bb9318.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/e2e7e72f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG Great Barrington 8.8/10 Excellent (702) "Everything was wonderful....super clean rooms, check-in was fast and smooth, staff was on top of everything. We definitely will be back at Holiday Inn. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tabitha CA $149 CA $167 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/be4af91d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/9aaa75ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 6:00 AM to 10:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/a2e409f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/549437da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Prospect Berkshires Egremont 9.6/10 Exceptional (15) "Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura CA $363 CA $453 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Great-Barrington-Hotels-Prospect-Berkshires.h116739795.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/a1ad800b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/fa93cb94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/44ab9667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/748b4faa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Monument Mountain Motel Great Barrington 9.0/10 Wonderful (801) "Yes it was clean & staff was very polite. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Barbara L. [](https://www.expedia.ca/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/1d183ca9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/a9be6743.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/1650f935.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Great Barrington 8.4/10 Very good (1000) "Clean room, nice location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Devron CA $106 CA $118 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/c5a54031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/7f86e411.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Non Smoking](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/a393dfb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, free cribs/infant beds, free rollaway beds](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/7c78ca51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Travelodge by Wyndham Great Barrington Berkshires Great Barrington 7.6/10 Good (561) "The staff were very friendly and accommodating " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tom CA $105 CA $117 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/9d0420c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/f2aaf746.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/15c993a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/32c535e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires Great Barrington 9.4/10 Exceptional (757) "Clean room, very courteous staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas CA $211 CA $236 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Great-Barrington-Hotels-Fairfield-Inn-Suites-By-Marriott-Great-Barrington-LenoxBerkshires.h913175.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/36b54e77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/aaa7fba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/c97f0de6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/6fb451ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Little Lion Great Barrington 8.6/10 Excellent (547) "The check-in was easy and the room was ready and clean. It was nice having our dogs with us. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria CA $154 CA $172 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/fbd2cba0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Private kitchen](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/61ae6bd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/75dbf9d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, blackout drapes](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/c0c5a00b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### East Rock Inn Great Barrington 9.4/10 Exceptional (36) "We had a great stay at East Rock Inn! Newly remodeled, clean room, comfortable bed, easy access to town. I will definitely stay there again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura CA $180 CA $202 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Great-Barrington-Hotels-East-Rock-Inn.h102806911.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/42000000/41180000/41178000/41178000/e7de1246.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor wedding](https://images.trvl-media.com/lodging/42000000/41180000/41178000/41178000/8bcde002.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/42000000/41180000/41178000/41178000/985aaf3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually furnished, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/42000000/41180000/41178000/41178000/3c75b29c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gedney Farm Great Barrington 9.2/10 Wonderful (132) "We loved our stay at Gedney. Michael was a sweetheart, and the grounds are GORGEOUS. We loved our room with fireplace - the whole setting is just country and updated/old. For anyone who loves farms and barns and rustic, this is for you. Can't wait to return." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lynda CA $259 CA $284 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Great-Barrington-Hotels-Gedney-Farm.h41178000.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/10000000/9720000/9716100/9716050/de957a5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/10000000/9720000/9716100/9716050/8a8cd518.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room 191, 1 Queen Bed, 1 Single Bed, 1 Sofa Bed](https://images.trvl-media.com/lodging/10000000/9720000/9716100/9716050/90de0046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room 191, 1 Queen Bed, 1 Single Bed, 1 Sofa Bed](https://images.trvl-media.com/lodging/10000000/9720000/9716100/9716050/267d369d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Old Inn On The Green Great Barrington 9.2/10 Wonderful (90) "Beautiful Inn and outstanding chef" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Catherine CA $426 CA $514 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Great-Barrington-Hotels-The-Old-Inn-On-The-Green.h9716050.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/e0f691bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/caf5dd09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/dcb799f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/52bc41a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home in Great Barrington Great Barrington 9.8/10 Exceptional (25) "Enjoyed our stay!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Fred W. CA $226 CA $379 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Great-Barrington-Hotels-Home-In-Great-Barrington.h84672833.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/c57b8d60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, eco-friendly cleaning products](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/780d89c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/406cc767.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/862ec0e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pet Friendly Riverfront Home in Great Barrington Great Barrington 9.4/10 Exceptional (6) CA $283 CA $416 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/772f14ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, printers](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/69c2e8f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/61aeb8a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/2cdfc6fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room Great Barrington 10/10 Exceptional (1) "Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roberta CA $791 CA $1,856 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Great-Barrington-Hotels-Berkshires-Best-Large-Deck-With-Hotub.h120149051.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/1bcf2f0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/505c31c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/64f95c5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, stereo](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/8d87241a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Great Barrington Get Away Great Barrington 9.4/10 Exceptional (25) "We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth G. CA $398 CA $724 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Great-Barrington-Hotels-Great-Barrington-Get-Away.h29615546.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103850000/103845900/103845853/e9c2fca2.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) ![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) ### Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer Great Barrington CA $433 CA $547 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Great-Barrington-Hotels-Close-To-Tanglewood-2BR-King-Bed-Fireplace-Sleeps-6-Mountain-View-Gem.h103845853.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/c0933de7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/f1aeba62.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) ![Coffee/tea maker, dining tables](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/5fd0e723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Element Lenox Berkshires Lenox 9.8/10 Exceptional (11) "New hotel very nice" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) joel CA $183 CA $204 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/3a8723ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room, 1 King Bed, Jetted Tub | Jetted tub](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/f3c92221.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed, Fireplace](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/4ea5ab50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Yankee, Trademark Collection by Wyndham Lenox 9.2/10 Wonderful (1014) "Great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ann CA $87 CA $98 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/8e50ee57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Suite, Private Bathroom (Catamount - Pets Allowed)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/13717808.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, Private Bathroom (Garden - Pets Allowed) | Miscellaneous](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/c68ae4d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Suite, Private Bathroom (Rockwell - No Pets)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/4d5a91f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Shaker Mill Inn West Stockbridge 9.6/10 Exceptional (436) "Nice place, easy check in" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $143 CA $157 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Non Lakeside Superior Room, 2 Queen beds](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/d3eea453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ba9d3ff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel Lee 9.0/10 Wonderful (1000) "The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elisabeth CA $137 CA $153 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/5acdf3c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/6b95ddf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/207845f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG Pittsfield 8.0/10 Very good (975) "Staff was very nice and helpful nice place restaurant was awesome great food and drinks" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Frank CA $130 CA $145 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.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=2025-12-17&endDate=2025-12-18®ionId=110336&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FGreat-Barrington-Chalets.d110336-aaChalets.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FGreat-Barrington-Chalets.d110336-aaChalets.Travel-Guide-Accommodation) ## Top Great Barrington Hotel Reviews ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Friendly staff, room was very clean. Pool area well maintained. Overall a great place to stay" [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Quality Inn](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg) ### Quality Inn 10/10 Excellent "Clean room, staff friendliness, near store and amenities." [](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.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 "Great service. Attentive staff. Great location. Rooms clean and comfortable. Thanks for another great stay! " [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c_y.jpg) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG 10/10 Excellent "We stayed over Thanksgiving and it did not disappoint. The customer service was great, the indoor pools were clean, there were tons of activities for kids even over the holiday. We will be back!" [](https://expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![Prospect Berkshires](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/b42c4262_y.jpg) ### Prospect Berkshires 10/10 Excellent "Wow, just wow! My high school friend and I met up at Prospect Berkshires for a girls weekend. We had an incredible time relaxing by using all the amenities. The staff are so helpful and profession. " [](https://expedia.ca/Great-Barrington-Hotels-Prospect-Berkshires.h116739795.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 "Everything was a great experience " [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.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 "Everything was great. " [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Monument Mountain Motel](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/fa93cb94_y.jpg) ### Monument Mountain Motel 10/10 Excellent "Great place to stay! " [](https://expedia.ca/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information) ![Travelodge by Wyndham Great Barrington Berkshires](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/7c78ca51_y.jpg) ### Travelodge by Wyndham Great Barrington Berkshires 10/10 Excellent "Very nice people at the desk, room was very nice" [](https://expedia.ca/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information) ## Find out more about Great Barrington ## Great Barrington Chalets information | Number of reviews | 8,100 | | --- | --- | | Accommodation | 5 Chalets | | Lowest Price | CA $98 | | Highest Price | CA $1,856 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [3 Star Hotels in Stockbridge](https://www.expedia.ca/3Star-Stockbridge-Hotels.s30-0-d162575.Travel-Guide-Filter-Hotels) - [Guest Houses in Alford](https://www.expedia.ca/Alford-Guest-Houses.d3000421226-aaGuestHouses.Travel-Guide-Accommodation) - 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