Western Massachusetts vacation rentals
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Top-rated vacation rentals in Western Massachusetts
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Western Massachusetts vacation rentals
Western Massachusetts fishing vacation rentals
Home in Southwick
4.99 out of 5 average rating, 184 reviewsLinny's Lakeview Cottage
Home in New Lebanon
4.99 out of 5 average rating, 350 reviewsThe old sawmill from 1771
Cottage in Ashfield
4.97 out of 5 average rating, 302 reviewshope house
Apartment in Great Barrington
4.95 out of 5 average rating, 321 reviewsPrivate En Suite in Beautiful Victorian
Cottage in Becket
4.96 out of 5 average rating, 135 reviewsCozy lakeside cottage
Home in Monterey
4.93 out of 5 average rating, 309 reviewsCharming cottage w/ gorgeous views.
Cottage in Becket
4.94 out of 5 average rating, 239 reviewsBERKSHIRE COTTAGE NEAR CRYSTAL CLEAR LAKE.
Tiny home in Brattleboro
4.86 out of 5 average rating, 173 reviews“Sugar Maple” Rustic Cabin Getaway with Fireplace
House rentals in Western Massachusetts
Home in Dalton
4.88 out of 5 average rating, 115 reviewsThe Yellow House
Home in Chester
4.96 out of 5 average rating, 314 reviewsRiverfront Getaway
Home in Pownal
4.99 out of 5 average rating, 215 reviewsCozy Vermont mini-house
Home in Bennington
4.99 out of 5 average rating, 241 reviewsCozy Modern Sugar House with spectacular views.
Home in Williamsburg
4.99 out of 5 average rating, 162 reviewsHilltown Studio
Home in Northampton
4.98 out of 5 average rating, 101 reviewsDiscover Cozy Elegance in the Heart of Northampton
Home in Great Barrington
4.96 out of 5 average rating, 215 reviewsJaw dropping mountain & lake views
Home in Becket
4.86 out of 5 average rating, 292 reviewsReal Estate:Therapy - Lake, Laundry, Love it
Lakefront house rentals in Western Massachusetts
Home in Becket
4.93 out of 5 average rating, 119 reviewsLake front retreat - Stylish Berkshire home
Home in Woodstock
4.94 out of 5 average rating, 272 reviewsWoodstock Historic Artist Estate - The Pond House
Home in Preston
5.0 out of 5 average rating, 123 reviewsNew Lake Front Home w/ Game Room & Stunning Views
Home in Coventry
5.0 out of 5 average rating, 110 reviewsWaterfront 10 min to Uconn outdoor tv gas fire pit
Home in Winchendon
4.79 out of 5 average rating, 149 reviewsWaterfront home 2 bedrooms withdeck beach and dock
Home in East Haddam
4.95 out of 5 average rating, 103 reviewsRomantic Getaway at The Lake!
Home in Ghent
4.87 out of 5 average rating, 272 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Home in Wappingers Falls
4.97 out of 5 average rating, 110 reviewsTranquil Tree-House on the beautiful Hudson River
Destinations to explore
- Cambridge Vacation rentals
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