House vacation rentals in Berkshire County
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Top-rated house rentals in Berkshire County
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 Berkshire County house rentals
House rentals with a pool
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
Sep 26 – Oct 3
Home in Sheffield
4.94 out of 5 average rating, 16 reviewsPrivate Berkshire County Retreat
Jun 15 – 22
Home in Cheshire
4.94 out of 5 average rating, 50 reviewsBerkshire County modern home + pool
Sep 12 – 19
Home in Dalton
4.89 out of 5 average rating, 81 reviewsPrivate & Stylish Berkshires House for All Seasons
Mar 4 – 11
Home in Great Barrington
4.97 out of 5 average rating, 34 reviewsNewly Remodeled Private Estate-Pool, Tennis Court!
Dec 2 – 9
Home in New Marlborough
4.95 out of 5 average rating, 21 reviewsBerkshires Colonial Farmhouse
Nov 12 – 19
Home in Great Barrington
5.0 out of 5 average rating, 52 reviewsStunning luxury home with pool
Nov 7 – 14
Home in West Stockbridge
5.0 out of 5 average rating, 6 reviewsPool is open Memorial Day Weekend! - Sleeps 13!
Nov 3 – 10
Weekly house rentals
Home in Monterey
4.93 out of 5 average rating, 116 reviewsPerfect Berkshire getaway.Cozy cottage.Great wifi.
Aug 16 – 23
Home in Canaan
4.9 out of 5 average rating, 150 reviewsBerkshire Lakefront House with Amazing Views
Jan 7 – 14
Home in North Adams
4.96 out of 5 average rating, 122 reviewsThe Lodge @ America’s Switzerland
Jul 25 – Aug 1
Home in Lenox
4.86 out of 5 average rating, 328 reviewsBerkshire, MA Getaway! Mile to town
Sep 10 – 17
Home in Lenox
4.96 out of 5 average rating, 170 reviewsLenox - Walk to Town - Berkshire Home
Nov 24 – Dec 1
Home in Becket
4.87 out of 5 average rating, 289 reviewsReal Estate:Therapy - Lake, Laundry, Love it
Aug 22 – 29
Home in Canaan
4.95 out of 5 average rating, 202 reviewsHudson River Valley/Berkshires
Jan 31 – Feb 7
Home in Becket
4.95 out of 5 average rating, 37 reviewsNerd Preservation Sanctuary
Dec 6 – 13
Private house rentals
Home in Cheshire
5.0 out of 5 average rating, 22 reviewsThe Berkshires Hummingbird House
Apr 2 – 9
Home in Becket
5.0 out of 5 average rating, 4 reviewsLakeside 3-BR Berkshires Residence
Mar 3 – 10
Home in Great Barrington
5.0 out of 5 average rating, 68 reviewsGranite Ledge, Modern home in a unique setting
Jan 12 – 19
Home in Great Barrington
4.97 out of 5 average rating, 38 reviewsWaterfront Modern Lake Mansfield Retreat
Jun 9 – 16
Home in Adams
4.91 out of 5 average rating, 68 reviewsMountain View Hideaway
Feb 18 – 25
Home in Lanesborough
4.92 out of 5 average rating, 25 reviewsHistoric Stone Church in The Berkshires
Aug 31 – Sep 7
Home in Becket
4.85 out of 5 average rating, 34 reviewsPrivate Cabin On Over 12 Acres Of Woods!
Apr 6 – 13
Home in Becket
5.0 out of 5 average rating, 13 reviewsLindal Cedar Berkshires Lake House
Feb 5 – 12
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