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

Guesthouse in Williamstown
4.96 out of 5 average rating, 189 reviewsBrookside Cottage
Top guest favourite

Home in Belchertown
4.97 out of 5 average rating, 79 reviewsMoonstone Lake House – romantic, serene, fun!
Top guest favourite

Treehouse in Guilford
4.99 out of 5 average rating, 153 reviewsCozy tent in the trees on organic flower farm
Guest favourite

Tiny homes in Granby
5 out of 5 average rating, 42 reviewsTiny House on Big, Pet-Friendly Farm
Top guest favourite

Cabin in Stoddard
4.98 out of 5 average rating, 110 reviewsBoulder House - Extraordinary Luxury in the Woods!
Guest favourite

Cabin in Petersburgh
4.93 out of 5 average rating, 242 reviewsCozy Retreat in the Trees
Top guest favourite

Cottage in Petersham
4.99 out of 5 average rating, 202 reviewsCider House Cottage
Guest favourite

Home in Lanesborough
4.96 out of 5 average rating, 55 reviewsHistoric Stone Church in The Berkshires
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- Rentals with pools Western Massachusetts
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- Six Flags New England
- Taconic State Park
- Berkshire East Mountain Resort
- Bushnell Park
- Jiminy Peak Mountain Resort
- Bash Bish Falls State Park
- Brimfield State Forest
- Kent Falls State Park
- Norman Rockwell Museum
- Catamount Mountain Ski Resort
- Mount Greylock Ski Club
- Albany Center Gallery
- Mount Snow Ski Resort
- Dinosaur State Park
- Bigelow Hollow State Park
- Mohawk Mountain Ski Area
- Hartford Golf Club
- Talcott Mountain State Park
- Beartown State Forest
- Wintonbury Hills Golf Course
- Mount Sugarloaf State Reservation
- Bright Nights at Forest Park
- Naumkeag
- Bousquet Mountain Ski Area