
Holiday rentals in Berkshire County
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Top-rated holiday 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 holiday rentals
Other great holiday rentals in Berkshire County
Guest favourite

Cottage in Great Barrington
4.92 out of 5 average rating, 93 reviewsCarriage house with Chef's Kitchen, close to town
Guest favourite

Guest house in Stockbridge
4.94 out of 5 average rating, 34 reviewsLight-filled Carpenter's Cottage in Stockbridge
Top guest favourite

Cottage in Sheffield
5 out of 5 average rating, 72 reviewsThe Blue Elm - A Historic Country Cottage
Guest favourite

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

Cabin in Becket
4.98 out of 5 average rating, 45 reviewsEntire Private Log Cabin in the Berkshires
Top guest favourite

Guest house in Williamstown
4.97 out of 5 average rating, 63 reviewsWalk to Williams * Steam Sauna * Ritz-Carlton Bed
Superhost

Home in Hillsdale
4.6 out of 5 average rating, 5 reviewsPrivate Getaway on large acreage
Top guest favourite

Cabin in Otis
5 out of 5 average rating, 10 reviewsBerkshires Lakefront Boho Modern Retreat
Destinations to explore
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- Rentals with a sauna Berkshire County
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- Bed and breakfasts Berkshire County
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- Rentals with a kayak Berkshire County
- Ski-in/ski-out rentals Berkshire County
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- Six Flags New England
- John Boyd Thacher State Park
- Taconic State Park
- Berkshire East Mountain Resort
- Bushnell Park
- Jiminy Peak Mountain Resort
- Zoom Flume
- Bash Bish Falls State Park
- Kent Falls State Park
- Norman Rockwell Museum
- Mount Greylock Ski Club
- Catamount Mountain Ski Resort
- Mount Snow Ski Resort
- Mohawk Mountain Ski Area
- Mount Sugarloaf State Reservation
- Albany Center Gallery
- Beartown State Forest
- Talcott Mountain State Park
- Hartford Golf Club
- Wintonbury Hills Golf Course
- Opus 40
- Bousquet Mountain Ski Area
- Bright Nights at Forest Park
- Hancock Shaker Village