House vacation rentals in The Berkshires
Find and book unique houses on Airbnb
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, 271 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 New Paltz
4.98 out of 5 average rating, 439 reviewsmidcentury modern in ground pool walk 2 trail/town
Home in Litchfield
4.93 out of 5 average rating, 166 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
Home in Cheshire
5.0 out of 5 average rating, 118 reviewsPool House
Home in Stormville
4.94 out of 5 average rating, 156 reviewsPrivate Hudson Valley Country Retreat
Home in Woodstock
4.91 out of 5 average rating, 213 reviewsJapanese Teahouse & Onsen, outside shower, tennis
Weekly house rentals
Home in Woodstock
4.91 out of 5 average rating, 643 reviewsDutch Touch Woodstock Cottage
Home in Dalton
4.88 out of 5 average rating, 115 reviewsThe Yellow House
Home in Germantown
4.95 out of 5 average rating, 365 reviewsAirbnb Magazine Featured Gorgeous Swedish Barn
Home in Lee
4.9 out of 5 average rating, 207 reviews1817 Berkshire Farmhouse- Close to Everything.
Home in Kerhonkson
5.0 out of 5 average rating, 213 reviewsCook House | Modern Cottage w/ Fireplace
Home in Wappingers Falls
4.97 out of 5 average rating, 109 reviewsTranquil Tree-House on the beautiful Hudson River
Home in Chatham
4.9 out of 5 average rating, 147 reviews2BR Chatham Vlg Home Wi-fi Park@Door Keyless 55"TV
Home in Bennington
4.99 out of 5 average rating, 241 reviewsCozy Modern Sugar House with spectacular views.
Private house rentals
Home in Manchester
4.94 out of 5 average rating, 176 reviewsParadise On The Hill Luxury Apartment.
Home in Ghent
4.9 out of 5 average rating, 259 reviewsRenovated guesthouse on 52 acres!
Home in Sheffield
4.9 out of 5 average rating, 107 reviewsWow! Best BERKSHIRE SnowHome #1 Private SuperClean
Home in Washington
4.85 out of 5 average rating, 172 reviewsCountry Home on a Hill
Home in Hudson
4.86 out of 5 average rating, 132 reviews19th Century Mill House with River View
Home in New Marlborough
4.89 out of 5 average rating, 122 reviewsLake House in the Berkshire (Access Dock & Canoe
Home in Schenectady
4.98 out of 5 average rating, 168 reviewsBright & Clean ~Tons of Upgrades ~Office Space
Home in Putney
4.94 out of 5 average rating, 340 reviewsVermont Botanical Studio Apartment
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