
Vacation rentals in Berkshire County
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Top-rated vacation rentals in Berkshire County
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Popular amenities for Berkshire County vacation rentals
Other great vacation rentals in Berkshire County
Guest favorite

Home in Canaan
4.95 out of 5 average rating, 56 reviewsPrivate Retreat: Hot Tub! Movie Room! Pool Table!
Guest favorite

Cottage in Great Barrington
4.92 out of 5 average rating, 91 reviewsCarriage house with Chef's Kitchen, close to town
Guest favorite

Home in Great Barrington
4.93 out of 5 average rating, 14 reviewsValley Vista atop Jug End
Top guest favorite

Loft in Great Barrington
5 out of 5 average rating, 19 reviewsThe Nest 5 min walk to downtown Great Barrington
Top guest favorite

Cottage in Sheffield
5 out of 5 average rating, 69 reviewsThe Blue Elm - A Historic Country Cottage
Top guest favorite

Cabin in Becket
5 out of 5 average rating, 8 reviewsWALK to lake! Dog friendly, A-Frame in Berkshires!
Guest favorite

Home in Egremont
4.91 out of 5 average rating, 82 reviewsModern and Stylish Country Lakeside Cottage
Top guest favorite

Guesthouse in Sheffield
5 out of 5 average rating, 17 reviewsBlack Bear Bungalow, Sheffield Mass. U Will Love!
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- Six Flags New England
- John Boyd Thacher State Park
- Taconic State Park
- Bushnell Park
- Berkshire East Mountain Resort
- Albany Center Gallery
- Jiminy Peak Mountain Resort
- Zoom Flume
- Bash Bish Falls State Park
- Kent Falls State Park
- Catamount Mountain Ski Resort
- Norman Rockwell Museum
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Beartown State Forest
- Hartford Golf Club
- Mohawk Mountain Ski Area
- Wintonbury Hills Golf Course
- Bright Nights at Forest Park
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Opus 40
- Pineridge Cross Country Ski Area
- Naumkeag