House vacation rentals in The Berkshires
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Top-rated house rentals in The Berkshires
Guests agree: these houses 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 The Berkshires house rentals
House rentals with a pool
Home in Ghent
4.87 out of 5 average rating, 272 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Home in Gloversville
4.97 out of 5 average rating, 317 reviewsIndoor Heated Pool in the Adirondacks
Home in Woodstock
4.98 out of 5 average rating, 101 reviewsWoodstock Historic Artist Estate- The Museum House
Home in Litchfield
4.93 out of 5 average rating, 166 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
Home in New Paltz
4.98 out of 5 average rating, 440 reviewsmidcentury modern in ground pool walk 2 trail/town
Home in Stormville
4.94 out of 5 average rating, 156 reviewsPrivate Hudson Valley Country Retreat
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
Home in Cheshire
5.0 out of 5 average rating, 119 reviewsPool House
Weekly house rentals
Home in Southwick
4.99 out of 5 average rating, 182 reviewsLinny's Lakeview Cottage
Home in Lee
4.9 out of 5 average rating, 207 reviews1817 Berkshire Farmhouse- Close to Everything.
Home in Becket
4.93 out of 5 average rating, 119 reviewsLake front retreat - Stylish Berkshire home
Home in Pownal
4.99 out of 5 average rating, 215 reviewsCozy Vermont mini-house
Home in Tyringham
4.91 out of 5 average rating, 107 reviewsBerkshire 4 bed Historic Farmhouse of Sir Kitson
Home in Monterey
4.93 out of 5 average rating, 117 reviewsPerfect Berkshire getaway.Cozy cottage.Great wifi.
Home in Dalton
4.88 out of 5 average rating, 115 reviewsThe Yellow House
Home in Chatham
4.9 out of 5 average rating, 148 reviews2BR Chatham Vlg Home Wi-fi Park@Door Keyless 55"TV
Private house rentals
Home in Hudson
4.86 out of 5 average rating, 132 reviews19th Century Mill House with River View
Home in Becket
4.95 out of 5 average rating, 38 reviewsNerd Preservation Sanctuary
Home in Stockbridge
4.94 out of 5 average rating, 95 reviewsBright Stockbridge country home, near everything!
Home in Lee
5.0 out of 5 average rating, 38 reviewsGreenHouse
Home in Otis
4.85 out of 5 average rating, 66 reviewsSpringtime Oasis in the Berkshires!
Home in Cornwall
4.98 out of 5 average rating, 54 reviewsThe Brookside Barn
Home in Berlin
4.96 out of 5 average rating, 24 reviewsCozy, 1779 Farmhouse, Upstate NY
Home in Becket
4.86 out of 5 average rating, 35 reviewsPrivate Cabin On Over 12 Acres Of Woods!
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