Title: Great Barrington Vacation Home Rentals from CA $494: Search Top Private Vacation Homes for Rent | 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](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/238000/238015-Great-Barrington.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Great Barrington Vacation Rentals ![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 prices for these dates In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=110336&startDate=2025-10-10&endDate=2025-10-12&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=110336&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=110336&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=110336&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Great Barrington Vacation Homes ## Our top choices for Great Barrington vacation homes ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33500000/33492300/33492239/a5ddb496.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33500000/33492300/33492239/85b23873.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/34000000/33500000/33492300/33492239/89102e9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33500000/33492300/33492239/63cb703a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table Pittsfield 9.8/10 Exceptional (147) "Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! " [](https://www.expedia.ca/Pittsfield-Hotels-Beautiful-8-Bedroom.h33492239.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/34000000/33710000/33704200/33704131/0d5d0135.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33710000/33704200/33704131/8aad64c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33710000/33704200/33704131/c214c777.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33710000/33704200/33704131/ae89362d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stockbridge Village in Summer Stockbridge 9.0/10 Wonderful (18) "This is a great home within walking distance of the interesting town of Stockbridge. The place is well equipped and has a charm consistent of what you can expect for a historic farm house. We would stay here again." [](https://www.expedia.ca/Stockbridge-Hotels-Stockbridge-Village-In-Summer.h33704131.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/52000000/51270000/51267800/51267781/7815c72a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/52000000/51270000/51267800/51267781/8f540e43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/52000000/51270000/51267800/51267781/15d1bd07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/52000000/51270000/51267800/51267781/12b8d7f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE Great Barrington 10/10 Exceptional (37) "We had the most wonderful trip! The location is perfect - easy access to downtown GB but still very relaxing and private. The kitchen is beautifully equipped and we ended up cooking most of our meals there. And the living room/great room led to hours of conversation. Can't wait to come back for a longer stay." [](https://www.expedia.ca/Great-Barrington-Hotels-NEWLY-REMODELED-3-BEDROOM-COUNTRY-CASTLE.h51267781.Hotel-Information) ![5 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/636f9a34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/d06b32cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/fb68a83f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/378fd21d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 5-bedroom house in charming Lee with WiFi Lee CA $405 CA $849 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Lee-Hotels-Spacious-5-Bedroom-House-In-Charming-Lee-With-WiFi.h117382215.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91600000/91593500/91593496/02c7301e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/92000000/91600000/91593500/91593496/e175fcb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/92000000/91600000/91593500/91593496/b2d17216.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91600000/91593500/91593496/960bf7a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amore Estate - beautiful room with many places to explore and relax in. Lenox 9.0/10 Wonderful (28) "Beautiful, spacious house in a great location!" [](https://www.expedia.ca/Lenox-Hotels-October-Mountain-Escape.h91593496.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/65000000/64150000/64145900/64145854/3d8d954d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/65000000/64150000/64145900/64145854/1e9190a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/65000000/64150000/64145900/64145854/4034ab20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/65000000/64150000/64145900/64145854/3e04c670.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location Lanesborough 9.6/10 Exceptional (72) "We love this comfortable cottage and quiet location, perfect for a relaxing vacation spent bird watching, biking the nearby rail trail, and hiking with our dog. This was our fourth time staying here-- impressed with the beautiful updates to the master bedroom, now a suite with its own bathroom! We'll be coming back again!" [](https://www.expedia.ca/Lanesborough-Hotels-Wildlife-Cottage-By-The-Lake.h64145854.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/56000000/55450000/55444500/55444452/38a8f79a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/56000000/55450000/55444500/55444452/dbfcb5d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/56000000/55450000/55444500/55444452/6afac8e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/56000000/55450000/55444500/55444452/100d9845.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bluebird Valley Farmhouse Millerton 10/10 Exceptional (69) "We stayed at the property while attending a family wedding. The house and yard were perfect. The best Vrbo we’ve ever stayed at. Would stay there again!" [](https://www.expedia.ca/Millerton-Hotels-Bluebird-Valley-Farmhouse.h55444452.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/34000000/33510000/33509100/33509020/2ae49251.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/34000000/33510000/33509100/33509020/afeca776.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33510000/33509100/33509020/461d5056.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33510000/33509100/33509020/d0befd42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### General Williams Estate House Lenox/Stockbridge Stockbridge 9.8/10 Exceptional (110) "The house was beautiful, the outdoor space was gorgeous, and the pool was amazing! I highly recommend this charming spot." [](https://www.expedia.ca/General-Williams-Estate-House-LenoxStockbridge.h33509020.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/665b8282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/f26544ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, computer monitors](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/af920cc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/99d3f85f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cheerful 3-bedroom cottage with woodstove Sheffield 10/10 Exceptional (39) "The property was centrally located for skiing, and was a comfortable stay." CA $328 CA $685 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Sheffield-Hotels-Cheerful-3-Bedroom-Cottage-With-Woodstove.h75599864.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/1993f238.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/9046d578.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/145ce996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/b7940a62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Walk into town, soak up sun on enclosed porch & steps away from nature trails! Stockbridge 10/10 Exceptional (25) "We had a wonderful time in this home. It accommodated our family of 4 easily. Several of us had to work the first day there and there were ample quiet spots and quality wifi for us. So easy to walk to town to restaurants etc" [](https://www.expedia.ca/Stockbridge-Hotels-Walk-Into-Town.h77128037.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/70000000/69770000/69763300/69763258/bf60ebb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/70000000/69770000/69763300/69763258/af8950e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/70000000/69770000/69763300/69763258/07ea0eda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/70000000/69770000/69763300/69763258/92cb5f01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hearts Desire is a furnished whole house in a small, colorful garden center. Lanesborough 10/10 Exceptional (93) "This was our third time at this property. We still love it and look forward to returning again." [](https://www.expedia.ca/Lanesborough-Hotels-Hearts-Desire-Is-A-Furnished-Whole-House-In-A-Small.h69763258.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/113000000/112430000/112429800/112429711/f28493a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/113000000/112430000/112429800/112429711/ab68c263.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, stereo](https://images.trvl-media.com/lodging/113000000/112430000/112429800/112429711/68050213.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112430000/112429800/112429711/b71e0d9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Falls Reach In The Heart of Copake Copake Falls [](https://www.expedia.ca/Copake-Falls-Hotels-Falls-Reach-In-The-Heart-Of-Copake.h112429711.Hotel-Information) ![Lake](https://images.trvl-media.com/lodging/19000000/18770000/18761000/18760908/8493ce06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/19000000/18770000/18761000/18760908/b603a1ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/19000000/18770000/18761000/18760908/786e1f41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18770000/18761000/18760908/270-12286aa8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks++ Lenox 9.4/10 Exceptional (60) "I had such a great stay with a bunch of friends at the Fox Hollow Estate. The house is exactly as described, and very spacious. At no point did I ever feel packed into the house, there are so many activities that you can do around the area. If you're visiting for foliage, the property has wonderful viewpoints and is within a close 20 or less minute drive to the best views. I would gladly stay at the place again if I was in the area." [](https://www.expedia.ca/Lenox-Hotels-Luxury-Fox-Hollow-Estate-Home-On-Laurel-Lake-Dream-Location.h18760908.Hotel-Information) ![Smart TV, fireplace, DVD player](https://images.trvl-media.com/lodging/79000000/78710000/78701100/78701034/be941bed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78710000/78701100/78701034/4ebdefe3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![7 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78710000/78701100/78701034/9e7f1a99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player](https://images.trvl-media.com/lodging/79000000/78710000/78701100/78701034/d795e81b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut! Great Barrington 10/10 Exceptional (27) "Spacious, welcoming, so well stocked, we felt lucky to find the property." [](https://www.expedia.ca/Great-Barrington-Hotels-Minutes-From-Ski-Butternut.h78701034.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99810000/99802600/99802538/a214acc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99810000/99802600/99802538/f46d5899.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/100000000/99810000/99802600/99802538/1853d2e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99810000/99802600/99802538/c7719f8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT Egremont 9.8/10 Exceptional (20) "We had a wonderful time, the property is lovely and the house is delightful." [](https://www.expedia.ca/South-Egremont-Hotels-Relax.h99802538.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/119000000/118470000/118467400/118467341/cb8efd3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118470000/118467400/118467341/3a77d3b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118470000/118467400/118467341/0bc1df65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/119000000/118470000/118467400/118467341/d975f5d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Whispering Estate Guest House - A Romantic Countryside Getaway Goshen 10/10 Exceptional (3) "Beautiful property and great location. A true retreat. " CA $1,001 CA $1,545 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Goshen-Hotels-Charming-Retreat-At-Stone-Hill-Estate-Nature-Meets-Luxury.h118467341.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/35000000/34010000/34008000/34007913/2800c888.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34010000/34008000/34007913/03d7dde0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/35000000/34010000/34008000/34007913/2cd290f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34010000/34008000/34007913/a4d043dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Enjoy comfortable elegance in this secluded grand home located in town Lenox 10/10 Exceptional (73) "Great location for access to both Tanglewood and Lenox center. " [](https://www.expedia.ca/Lenox-Hotels-Enjoy-Comfortable-Elegance-In-This-Secluded-Grand-Home-Located-In-Town.h34007913.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/98000000/97100000/97094700/97094615/3374cc72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/98000000/97100000/97094700/97094615/9046410c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/98000000/97100000/97094700/97094615/7863f467.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/98000000/97100000/97094700/97094615/0c17f0c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG! Craryville 9.6/10 Exceptional (30) "Well located and comfortable " [](https://www.expedia.ca/Craryville-Hotels-COZY-LAKE-SKI-HOME-FOR-FAMILY-OF-5-BRING-YOUR-DOG.h97094615.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/7377fc19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/0e82b119.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/508c5b2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/20000000/19110000/19107300/19107245/af5c0679.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Big farmhouse in the foothills of the Berkshires Russell 10/10 Exceptional (140) "Lovely old farmhouse with authentic yet comfortable furnishings. Would recommend!" CA $277 CA $494 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Russell-Hotels-Big-Farmhouse-In-The-Foothills-Of-The-Berkshires.h19107245.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39960000/39954400/39954364/c74b811e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39960000/39954400/39954364/c3f7f916.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/40000000/39960000/39954400/39954364/392c12f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/40000000/39960000/39954400/39954364/c7aa0091.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB! Great Barrington 10/10 Exceptional (55) "We loved Manor Lane! It had every amenity you could ask for. The house is fun and charming and there are thoughtful touches everywhere you look! We had fun watching movies in the living room, playing games in the lounge, cooking family meals in the spectacular kitchen and playing tennis in the sunshine. A perfect 10!" [](https://www.expedia.ca/Great-Barrington-Hotels-Premiere-Berkshire-Country-Estate-W-Private-Pool-Tennis-Court-5-Mins-To-GB.h39954364.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=2025-10-09&endDate=2025-10-10®ionId=110336&adults=2&lodging=VACATION_HOME&sort=RECOMMENDED&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-Private-Vacation-Homes.d110336-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FGreat-Barrington-Private-Vacation-Homes.d110336-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Great Barrington Hotel Reviews ![Holiday Inn Express Hotel & Suites Great Barrington by IHG](//images.trvl-media.com/lodging/1000000/900000/892300/892229/4c557ede_y.jpg) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG 10/10 Excellent "Probably the nicest Holiday Inn Express we've stayed at. Clean, well-appointed rooms. Everything looks updated. And did I say clean?Really excellent coffee and generous hot breakfast. Friendly and helpful desk staff. " [](https://expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ![Monument Mountain Motel](//images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/fa93cb94_y.jpg) ### Monument Mountain Motel 10/10 Excellent "Good value for the price" [](https://expedia.ca/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information) ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](//images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "Valerie at the front desk and who checked me in was above and beyond in customer service. She checked to see if I had a IGH account—which I did but had forgotten, and reminded me about the points and promotions. This Holiday Inn is a well managed property. Thank you" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](//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 for 5 nights and really enjoyed the surroundings and the drive to the property. The area is peaceful and quiet, with plenty to do for kids, including a mountain hike that even our 2- and 6-year-olds managed well. The grounds are beautiful for photos, very well maintained, and we often saw the crew cleaning and painting the sidewalks. I booked 2 suites, which were a good size for a family of four and offered plenty of space. The only downsides were that check-in felt a bit tedious it took several tries to swipe my card and there was no housekeeping service or follow-up to check on amenities during our stay. A self check-in option would make things smoother. Overall, we loved the quietness, the family-friendly activities, and the clean, well-kept property. With a few improvements in guest service, this could easily be a 5-star experience." [](https://expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![Berkshire Mountain Lodge](//images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Excellent location. Friendly staff. " [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.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 "A great place if you appreciate and like history. The lobby is filled with antiques and the porch is great to rock in a chair and sip some wine. Parking is no issue and you can walk to local restaurants and shops. " [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](//images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "With spa, fireplace and canopy over the bed it was the perfect treat for myself!" [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires](//images.trvl-media.com/lodging/1000000/920000/913200/913175/1d50a551_y.jpg) ### Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires 10/10 Excellent "Otto couldn’t have been more helpful at checkin. Great recommendations for hotels and places to go." [](https://expedia.ca/Great-Barrington-Hotels-Fairfield-Inn-Suites-By-Marriott-Great-Barrington-LenoxBerkshires.h913175.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/30000/20500/20447/588051f1_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 10/10 Excellent "I had a great stay at this comfortable, homey, family owned inn. The beds were vrry comfortable and the rooms had everything I needed including a fridge, lots of towels, a hair dryer etc. The property is clean, safe and very quiet. There’s an Indian restaurant on site with delicious food and a bar. The lake is lovely; I enjoyed a relaxing time sitting by the lake with my dog. The breakfast was good and the breakfast room has a gorgeous view of the lake. I will definitely be back for another stay." [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ## Find out more about Great Barrington ## Great Barrington Vacation Homes information | Number of reviews | 845 | | --- | --- | | Accommodation | 616 Vacation Homes | | Lowest Price | CA $494 | | Highest Price | CA $1,545 | ## 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) - [Alford Hotels](https://www.expedia.ca/Alford-Hotels.d3000421226.Travel-Guide-Hotels) - [Lodges in Alford](https://www.expedia.ca/Alford-Lodges.d3000421226-aaLodges.Travel-Guide-Accommodation) - [Hotels near Berkshire Botanical Garden](https://www.expedia.ca/Berkshire-Botanical-Garden-Hotels.0-l553248621532665247-0.Travel-Guide-Filter-Hotels) - 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