
Holiday rentals in Western Massachusetts
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Top-rated holiday rentals in Western Massachusetts
Guests agree: these stays are highly rated for location, cleanliness and more.
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Popular amenities for Western Massachusetts holiday rentals
Other great holiday rentals in Western Massachusetts
Top guest favourite

Treehouse in Wallkill
4.99 out of 5 average rating, 317 reviewsThe Treecastle at the Roundhouse Homestead
Top guest favourite

Home in Belchertown
4.99 out of 5 average rating, 74 reviewsMoonstone Lake House – romantic, serene, fun!
Top guest favourite

Chalet in Charlemont
4.99 out of 5 average rating, 107 reviewsThe Lodge on Warner Hill
Top guest favourite

Flat in Northampton
4.92 out of 5 average rating, 632 reviewsSunny Peaceful Home
Top guest favourite

Cottage in Petersham
4.99 out of 5 average rating, 200 reviewsCider House Cottage
Top guest favourite

Guest house in Guilford
5 out of 5 average rating, 41 reviewsPeaceful forest cottage getaway
Guest favourite

Home in Lanesborough
4.96 out of 5 average rating, 51 reviewsHistoric Stone Church in The Berkshires
Top guest favourite

Farm stay in Worthington
4.97 out of 5 average rating, 35 reviewsLike sleeping on a cloud
Destinations to explore
- Hudson Valley Holiday rentals
- Boston Holiday rentals
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- Plainview Holiday rentals
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- Farm stay rentals Western Massachusetts
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- Six Flags New England
- Bushnell Park
- Taconic State Park
- Jiminy Peak Mountain Resort
- Albany Center Gallery
- Berkshire East Mountain Resort
- Bash Bish Falls State Park
- Catamount Mountain Ski Resort
- Kent Falls State Park
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Brimfield State Forest
- Norman Rockwell Museum
- Beartown State Forest
- Dinosaur State Park
- Mohawk Mountain Ski Area
- Bright Nights at Forest Park
- Hartford Golf Club
- Bigelow Hollow State Park
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Pineridge Cross Country Ski Area
- Naumkeag
- Clarksburg State Park