
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
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Popular amenities for Great Barrington holiday rentals
Other great holiday rentals in Great Barrington
Top guest favourite

Home in Great Barrington
4.98 out of 5 average rating, 56 reviewsWaterfront Modern Lake Mansfield Retreat
Guest favourite

Home in Great Barrington
4.96 out of 5 average rating, 49 reviewsRiver Cottage: Riverfront Home, Walkable Community
Top guest favourite

Home in Great Barrington
5 out of 5 average rating, 86 reviewsWalk to Town! Great Barrington 4-bedroom farmhouse
Guest favourite

Guest house in Great Barrington
5 out of 5 average rating, 12 reviewsBerkshires Guest Barn
Guest favourite

Home in Egremont
4.91 out of 5 average rating, 82 reviewsModern and Stylish Country Lakeside Cottage
Guest favourite

Home in Great Barrington
4.97 out of 5 average rating, 35 reviewsCharming Cottage - Walk To Town
Guest favourite

Home in Great Barrington
4.9 out of 5 average rating, 69 reviewsWalk to Town/Lake – Spring ’25 Renovation!
Top guest favourite

Guest suite in Sheffield
5 out of 5 average rating, 80 reviewsThe Sunset Suite~Great South Berkshire Location!
Quick stats about holiday rentals in Great Barrington
Total rentals
240 properties
Total number of reviews
10K reviews
Family-friendly rentals
160 properties are a good fit for families
Pet-friendly rentals
120 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
140 properties have a dedicated workspace
Destinations to explore
- Hudson Valley Holiday rentals
- Long Island Holiday rentals
- Plainview Holiday rentals
- The Hamptons Holiday rentals
- East River Holiday rentals
- New York Holiday rentals
- Boston Holiday rentals
- Pocono Mountains Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Montreal Holiday rentals
- Rentals with a fireplace Great Barrington
- Family-friendly rentals Great Barrington
- Rentals with a firepit Great Barrington
- Cabin rentals Great Barrington
- Pet-friendly rentals Great Barrington
- Family-friendly rentals Great Barrington
- Fitness-friendly rentals Great Barrington
- Rentals with pools Great Barrington
- House rentals Great Barrington
- Rentals with a hot tub Great Barrington
- Rentals with outdoor seating Great Barrington
- Waterfront rentals Great Barrington
- Rentals with a patio Great Barrington
- Flat rentals Great Barrington
- Rentals with a kayak Great Barrington
- Rentals with a washing machine and dryer Great Barrington
- Rentals with lake access Great Barrington
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- Hunter Mountain
- Six Flags New England
- Thunder Ridge Ski Area
- John Boyd Thacher State Park
- Taconic State Park
- Bushnell Park
- Berkshire East Mountain Resort
- Albany Center Gallery
- Jiminy Peak Mountain Resort
- Zoom Flume
- Walkway Over the Hudson State Historic Park
- Bash Bish Falls State Park
- Kent Falls State Park
- Catamount Mountain Ski Resort
- Norman Rockwell Museum
- Mount Greylock Ski Club
- Windham Mountain
- Beartown State Forest
- Hartford Golf Club
- Mohawk Mountain Ski Area
- Mount Southington Ski Area
- Wintonbury Hills Golf Course
- Bright Nights at Forest Park
- Hancock Shaker Village