
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

Barn in East Chatham
4.98 out of 5 average rating, 88 reviewsLuxury Barn Retreat — All-Season Escape Awaits!
Superhost

Home in Lee
4.8 out of 5 average rating, 5 reviewsLakeside Getaway at Goose Pond!
Top guest favourite

Loft in Great Barrington
5 out of 5 average rating, 29 reviewsThe Nest 5 min walk to downtown Great Barrington
Guest favourite

Cabin in Becket
5 out of 5 average rating, 20 reviewsWALK to lake! Dog friendly, Kayaks, A-Frame, Hike
Top guest favourite

Home in Great Barrington
4.99 out of 5 average rating, 77 reviewsStunning luxury home with pool
Top guest favourite

Cabin in Becket
4.96 out of 5 average rating, 54 reviewsEntire Private Log Cabin in the Berkshires
Top guest favourite

Home in Lanesborough
5 out of 5 average rating, 25 reviewsMountain Blossom Retreat by Evergreen Home
Top guest favourite

Cabin in Florida
5 out of 5 average rating, 13 reviewsThe Greylock Cabin
Destinations to explore
- Rentals with breakfast Berkshire County
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- Pet-friendly rentals Berkshire County
- Rentals with a firepit Berkshire County
- Ski-in/ski-out rentals Berkshire County
- Hotel rentals Berkshire County
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- Rentals with a hot tub Berkshire County
- Rentals with a sauna Berkshire County
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- Rentals with a kayak Berkshire County
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- Rentals with an EV charger Berkshire County
- Bed and breakfasts Berkshire County
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- Rentals with a fireplace Berkshire County
- Rentals with lake access Berkshire County
- Chalet rentals Berkshire County
- Rentals with a patio Berkshire County
- Rentals with pools Berkshire County
- Farm stay rentals Berkshire County
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- Rentals with beach access Berkshire County
- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- John Boyd Thacher State Park
- Bash Bish Falls State Park
- Zoom Flume
- Bushnell Park
- Catamount Mountain Ski Resort
- Kent Falls State Park
- Norman Rockwell Museum
- Wintonbury Hills Golf Course
- Mount Greylock Ski Club
- Taconic State Park
- Mohawk Mountain Ski Area
- Mount Tom State Reservation
- Mount Sugarloaf State Reservation
- Beartown State Forest
- Bousquet Mountain Ski Area
- Albany Center Gallery
- Hartford Golf Club
- Hancock Shaker Village
- Northern Cross Vineyard
- Opus 40
- Peebles Island State Park