
Vacation rentals in Berkshire County
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Top-rated vacation rentals in Berkshire County
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Popular amenities for Berkshire County vacation rentals
Other great vacation rentals in Berkshire County
Top guest favorite

Loft in Great Barrington
5 out of 5 average rating, 20 reviewsThe Nest 5 min walk to downtown Great Barrington
Guest favorite

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

Cottage in Sheffield
5 out of 5 average rating, 70 reviewsThe Blue Elm - A Historic Country Cottage
Guest favorite

Barn in Monterey
5 out of 5 average rating, 21 reviewsA Writer's Retreat at The Barn
Top guest favorite

Guesthouse in Williamstown
4.97 out of 5 average rating, 62 reviewsWalk to Williams * Steam Sauna * Ritz-Carlton Bed
Top guest favorite

Cabin in Otis
5 out of 5 average rating, 9 reviewsBerkshires Lakefront Boho Modern Retreat
Top guest favorite

Cottage in Monterey
5 out of 5 average rating, 62 reviewsBeaver Lodge
Guest favorite

Home in Pittsfield
4.96 out of 5 average rating, 77 reviewsBerkshire Getaway Ranch 3 acres + saltwater pool
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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
- Zoom Flume
- Jiminy Peak Mountain Resort
- Bash Bish Falls State Park
- Mount Greylock Ski Club
- Kent Falls State Park
- Norman Rockwell Museum
- Catamount Mountain Ski Resort
- Mount Snow Ski Resort
- Mohawk Mountain Ski Area
- Beartown State Forest
- Wintonbury Hills Golf Course
- Talcott Mountain State Park
- Hartford Golf Club
- Mount Sugarloaf State Reservation
- Bousquet Mountain Ski Area
- Bright Nights at Forest Park
- Hancock Shaker Village
- Opus 40
- Family travel hub Tips and inspiration
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- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes