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 Woodstock
4.98 out of 5 average rating, 101 reviewsWoodstock Historic Artist Estate- The Museum House
Sep 6 – 13
Home in Ghent
4.87 out of 5 average rating, 270 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Mar 22 – 29
Home in Gloversville
4.97 out of 5 average rating, 315 reviewsIndoor Heated Pool in the Adirondacks
Apr 23 – 30
Home in Litchfield
4.93 out of 5 average rating, 163 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
Sep 12 – 19
Home in New Paltz
4.98 out of 5 average rating, 437 reviewsmidcentury modern in ground pool walk 2 trail/town
Jul 14 – 21
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
Sep 13 – 20
Home in Stormville
4.94 out of 5 average rating, 156 reviewsPrivate Hudson Valley Country Retreat
Dec 27 – Jan 3
Home in Cheshire
5.0 out of 5 average rating, 118 reviewsPool House
Nov 16 – 23
Weekly house rentals
Home in Dalton
4.88 out of 5 average rating, 114 reviewsThe Yellow House
Nov 28 – Dec 5
Home in Kerhonkson
5.0 out of 5 average rating, 212 reviewsCook House | Modern Cottage w/ Fireplace
Dec 8 – 15
Home in Becket
4.93 out of 5 average rating, 118 reviewsLake front retreat - Stylish Berkshire home
Sep 12 – 19
Home in Williamsburg
4.99 out of 5 average rating, 158 reviewsHilltown Studio
Jan 19 – 26
Home in Pittsfield
4.98 out of 5 average rating, 102 reviewsHidden Oasis in the Mountains by Evergreen Home
Oct 30 – Nov 6
Home in Bennington
4.99 out of 5 average rating, 238 reviewsCozy Modern Sugar House with spectacular views.
Feb 7 – 14
Home in Egremont
4.97 out of 5 average rating, 112 reviewsA sunny, quiet chalet beautifully decorated.
Apr 16 – 23
Home in Monterey
4.93 out of 5 average rating, 116 reviewsPerfect Berkshire getaway.Cozy cottage.Great wifi.
Jun 17 – 24
Private house rentals
Home in Stockbridge
4.95 out of 5 average rating, 91 reviewsBright Stockbridge country home, near everything!
Dec 23 – 30
Home in Becket
4.85 out of 5 average rating, 34 reviewsPrivate Cabin On Over 12 Acres Of Woods!
Dec 11 – 18
Home in Lee
5.0 out of 5 average rating, 36 reviewsGreenHouse
Oct 15 – 22
Home in Cornwall
4.98 out of 5 average rating, 53 reviewsThe Brookside Barn
Jan 1 – 8
Home in Otis
4.84 out of 5 average rating, 61 reviewsSpringtime Oasis in the Berkshires!
Jun 2 – 9
Home in Milan
5.0 out of 5 average rating, 21 reviewsModernist Wooded Retreat Rhinebeck on 75 acres
Mar 13 – 20
Home in Great Barrington
5.0 out of 5 average rating, 68 reviewsGranite Ledge, Modern home in a unique setting
Oct 30 – Nov 6
Home in Great Barrington
4.97 out of 5 average rating, 38 reviewsWaterfront Modern Lake Mansfield Retreat
Oct 24 – 31
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