Berkshires Vacation Home Rentals

Rent a Berkshires cabin or vacation rental and you’ll be ideally situated to enjoy the mountains, rivers, and cultural attractions of western Massachusetts. Summer house rentals in the Berkshires are very popular, so be sure to book early for the best selection of rentals.

Berkshires vacation rentals make a great base for experiencing the natural beauty of this area, from fishing and rafting on the Hoosic and Housatonic rivers, to hiking and biking on the Mohawk Trail and other paths.

The Berkshires region is also known for its picturesque New England towns, such as Stockbridge, and variety of cultural attractions. Summertime guests of Berkshires vacation rentals can attend music and theatre festivals at Jacob's Pillow, Tanglewood, and Williamstown.

Guests of Stockbridge and West Stockbridge vacation rentals can visit the Norman Rockwell Museum, the Berkshire Scenic Railway Museum, and the Berkshire Botanical Garden.

Other popular accommodations in the Berkshires include Becket, Great Barrington, Lenox, Monterey, Otis, Richmond, and Stockbridge vacation rentals.

From cozy mountain cabins to family-friendly vacation homes, there’s a Berkshires vacation rental that’s perfect for you. Book your Berkshires rental today for the best selection!

Pet friendly Berkshires/ Western Massachusetts vacation rentals
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Berkshires Vacation Rentals by Owner

Featured Listings


New Marlborough



Great Barrington

Charlemont apartment photo - Rolling up to the chalet Property Details Berkshires,
2 bedrooms, sleeps 6
New Marlborough house photo - Front view of house Property Details Berkshires,
5 bedrooms, sleeps 11
Lenox apartment photo - Currently being renovated. Property Details Berkshires,
3 bedrooms, sleeps 4
Lenox house 3698190 picture Property Details Berkshires,
5 bedrooms, sleeps 12
Great Barrington cottage photo - The Cove: 360 feet of private waterfront. Property Details Berkshires,
2 bedrooms, sleeps 6
Adams Alford Ashfield Becket Charlemont Cheshire Chesterfield Cummington Dalton Egremont Goose Pond Great Barrington Hinsdale Jiminy Peak Lanesboro Lee Lenox Middlefield Mill River Monterey New Marlborough North Adams North Egremont Norwich Lake Otis Pittsfield Richmond Sandisfield Savoy Sheffield Shelburne Falls Stockbridge Tolland Tyringham West Stockbridge Williamstown

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