House holiday rentals in Western Massachusetts
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Top-rated house rentals in Western Massachusetts
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Western Massachusetts house rentals
House rentals with a pool
Home in Colrain
4.88 out of 5 average rating, 112 reviewsThe 1770 House
Home in Ghent
4.87 out of 5 average rating, 271 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Home in Litchfield
4.93 out of 5 average rating, 165 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
Home in Deerfield
4.81 out of 5 average rating, 187 reviewsPerfectly Polished Deerfield Home 5 min to I-91
Home in Keene
4.93 out of 5 average rating, 183 reviewsThe Brick House on Washington Street
Home in Wilmington
4.9 out of 5 average rating, 132 reviews4 bedroom Ski House 15 min to Mount Snow
Home in Woodstock
4.93 out of 5 average rating, 210 reviewsCedar Ridge
Weekly house rentals
Home in North Adams
4.96 out of 5 average rating, 122 reviewsThe Lodge @ America’s Switzerland
Home in Becket
4.93 out of 5 average rating, 118 reviewsLake front retreat - Stylish Berkshire home
Home in Huntington
4.9 out of 5 average rating, 109 reviewsPrivate house on the River
Home in Rhinebeck
4.91 out of 5 average rating, 256 reviewsArchitectural wonder in the woods
Home in Manchester
4.94 out of 5 average rating, 176 reviewsParadise On The Hill Luxury Apartment.
Home in Canaan
5.0 out of 5 average rating, 135 reviewsCountry Cottage
Home in Lee
5.0 out of 5 average rating, 234 reviewsBerkshire Mountain retreat with Urban eco-luxuries
Home in Germantown
4.95 out of 5 average rating, 364 reviewsAirbnb Magazine Featured Gorgeous Swedish Barn
Private house rentals
Home in Dalton
4.92 out of 5 average rating, 171 reviewsBrooksong, the perfect Berkshires getaway
Home in Greenfield
4.88 out of 5 average rating, 164 reviewsPeaceful Blossoms Victorian Home
Home in Winchendon
4.8 out of 5 average rating, 145 reviewsWaterfront home 2 bedrooms withdeck beach and dock
Home in Hudson
4.86 out of 5 average rating, 132 reviews19th Century Mill House with River View
Home in Granby
4.82 out of 5 average rating, 159 reviewsClean, Spacious 3 BR Half-Duplex on Quiet 4+ Acres
Home in Rhinebeck
5.0 out of 5 average rating, 165 reviewsEagle Rock House
Home in Dalton
5.0 out of 5 average rating, 34 reviewsCleveland House - renovated Berkshires' gem.
Home in Germantown
4.96 out of 5 average rating, 260 reviewsModern Cottage, Views, Walking Trails, Fireplace!
Destinations to explore
- Cambridge Accommodation & holiday rentals
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