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
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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
Jul 8 – 15
Home in Cheshire
4.94 out of 5 average rating, 50 reviewsBerkshire County modern home + pool
Mar 14 – 21
Home in Dalton
4.89 out of 5 average rating, 80 reviewsPrivate & Stylish Berkshires House for All Seasons
Jun 10 – 17
Home in Sheffield
4.94 out of 5 average rating, 16 reviewsPrivate Berkshire County Retreat
Jun 10 – 17
Home in Great Barrington
4.97 out of 5 average rating, 33 reviewsNewly Remodeled Private Estate-Pool, Tennis Court!
Jan 25 – Feb 1
Home in New Marlborough
4.95 out of 5 average rating, 21 reviewsBerkshires Colonial Farmhouse
Dec 11 – 18
Home in Great Barrington
5.0 out of 5 average rating, 52 reviewsStunning luxury home with pool
Sep 28 – Oct 5
Home in Pittsfield
4.97 out of 5 average rating, 38 reviewsBerkshire Lakefront Home W/Pool-100%Renovated
Dec 9 – 16
Weekly house rentals
Home in Canaan
4.95 out of 5 average rating, 202 reviewsHudson River Valley/Berkshires
Dec 7 – 14
Home in Canaan
4.9 out of 5 average rating, 150 reviewsBerkshire Lakefront House with Amazing Views
Jan 2 – 9
Home in North Adams
4.96 out of 5 average rating, 121 reviewsThe Lodge @ America’s Switzerland
Jul 25 – Aug 1
Home in Lenox
4.93 out of 5 average rating, 209 reviewsHeart of Lenox Walk to Town Cozy Cottage!
Sep 14 – 21
Home in Lenox
4.86 out of 5 average rating, 328 reviewsBerkshire, MA Getaway! Mile to town
May 12 – 19
Home in Becket
4.86 out of 5 average rating, 287 reviewsReal Estate:Therapy - Lake, Laundry, Love it
Nov 12 – 19
Home in Huntington
4.9 out of 5 average rating, 109 reviewsPrivate house on the River
Jan 26 – Feb 2
Home in Lenox
4.96 out of 5 average rating, 170 reviewsLenox - Walk to Town - Berkshire Home
May 19 – 26
Private house rentals
Home in Otis
4.83 out of 5 average rating, 59 reviewsSpringtime Oasis in the Berkshires!
Jun 19 – 26
Home in Berlin
4.96 out of 5 average rating, 24 reviewsCozy, 1779 Farmhouse, Upstate NY
Nov 29 – Dec 6
Home in Cheshire
5.0 out of 5 average rating, 22 reviewsThe Berkshires Hummingbird House
Nov 15 – 22
Home in Adams
4.91 out of 5 average rating, 68 reviewsMountain View Hideaway
Sep 6 – 13
Home in Great Barrington
5.0 out of 5 average rating, 67 reviewsGranite Ledge, Modern home in a unique setting
Nov 27 – Dec 4
Home in Becket
5.0 out of 5 average rating, 3 reviewsLakeside 3-BR Berkshires Residence
Jan 15 – 22
Home in Great Barrington
4.97 out of 5 average rating, 38 reviewsWaterfront Modern Lake Mansfield Retreat
Jun 9 – 16
Home in Great Barrington
5.0 out of 5 average rating, 3 reviewsWalt's Townhouse - Berkshire living at its best
Sep 29 – Oct 6
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