Holiday rentals in Great Barrington
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Top-rated holiday rentals in Great Barrington
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Great Barrington holiday rentals
Stay near Great Barrington's top sights
Other great holiday rentals in Great Barrington
Guest favourite
Cottage in Hillsdale
4.94 out of 5 average rating, 171 reviewsCozy Cottage Catamount, Berkshires Walk to Brewery
Guest favourite
Farm stay in Pittsfield
4.99 out of 5 average rating, 107 reviewsPrivate 2nd-floor studio on a working produce farm
Guest favourite
Guest suite in Great Barrington
5.0 out of 5 average rating, 47 reviewsSweet 1-bedroom with salt water pool
Guest favourite
Flat in Great Barrington
4.95 out of 5 average rating, 19 reviewsKing Bed|2mi Ski Resort|Fast Wi-Fi|Studio|
Guest favourite
Guest house in Great Barrington
4.97 out of 5 average rating, 90 reviewsStudio in Bucolic Berkshire Setting
Guest favourite
Barn in Great Barrington
5.0 out of 5 average rating, 49 reviewsSerene Renovated Barn w/ Firepit
Guest favourite
Home in Great Barrington
5.0 out of 5 average rating, 9 reviewsCharming Cottage - Walk To Town
Guest favourite
Home in Great Barrington
4.97 out of 5 average rating, 38 reviewsWaterfront Modern Lake Mansfield Retreat
Quick stats about holiday rentals in Great Barrington
Total rentals
250 properties
Rentals with dedicated workspaces
140 properties have a dedicated workspace
Rentals with a pool
30 properties have a pool
Pet-friendly rentals
120 properties allow pets
Family-friendly rentals
180 properties are a good fit for families
Total number of reviews
8.4K reviews
Destinations to explore
- New City Holiday rentals
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- Family-friendly rentals Great Barrington
- Rentals with a kayak Great Barrington
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- Family-friendly rentals Great Barrington
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- Rentals with a hot tub Great Barrington
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