House vacation rentals in Berkshire County
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Top-rated house rentals in Berkshire County
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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
Oct. 15 – 22
Home in Sheffield
4.94 out of 5 average rating, 16 reviewsPrivate Berkshire County Retreat
Jun. 13 – 20
Home in Cheshire
4.94 out of 5 average rating, 50 reviewsBerkshire County modern home + pool
Jun. 12 – 19
Home in Dalton
4.89 out of 5 average rating, 81 reviewsPrivate & Stylish Berkshires House for All Seasons
May 7 – 14
Home in Lee
4.98 out of 5 average rating, 62 reviewsBerkshire Vacation Home in Lee (Pool Opens in May)
Oct. 17 – 24
Home in Great Barrington
4.97 out of 5 average rating, 34 reviewsNewly Remodeled Private Estate-Pool, Tennis Court!
Nov. 28 – Dec. 5
Home in New Marlborough
4.95 out of 5 average rating, 21 reviewsBerkshires Colonial Farmhouse
Dec. 1 – 8
Home in Great Barrington
5.0 out of 5 average rating, 52 reviewsStunning luxury home with pool
Nov. 7 – 14
Weekly house rentals
Home in Becket
4.87 out of 5 average rating, 289 reviewsReal Estate:Therapy - Lake, Laundry, Love it
Feb. 21 – 28
Home in Canaan
4.9 out of 5 average rating, 150 reviewsBerkshire Lakefront House with Amazing Views
Jan. 5 – 12
Home in North Adams
4.96 out of 5 average rating, 122 reviewsThe Lodge @ America’s Switzerland
Jul. 25 – Aug. 1
Home in Lenox
4.93 out of 5 average rating, 210 reviewsHeart of Lenox Walk to Town Cozy Cottage!
Oct. 14 – 21
Home in Lenox
4.86 out of 5 average rating, 328 reviewsBerkshire, MA Getaway! Mile to town
May 26 – Jun. 2
Home in Canaan
4.95 out of 5 average rating, 202 reviewsHudson River Valley/Berkshires
Dec. 10 – 17
Home in Egremont
4.97 out of 5 average rating, 112 reviewsA sunny, quiet chalet beautifully decorated.
Aug. 17 – 24
Home in Lenox
4.96 out of 5 average rating, 170 reviewsLenox - Walk to Town - Berkshire Home
May 12 – 19
Private house rentals
Home in Berlin
4.96 out of 5 average rating, 24 reviewsCozy, 1779 Farmhouse, Upstate NY
Dec. 23 – 30
Home in Cheshire
5.0 out of 5 average rating, 22 reviewsThe Berkshires Hummingbird House
Apr. 6 – 13
Home in Adams
4.91 out of 5 average rating, 68 reviewsMountain View Hideaway
Feb. 20 – 27
Home in Great Barrington
5.0 out of 5 average rating, 68 reviewsGranite Ledge, Modern home in a unique setting
Oct. 8 – 15
Home in Becket
5.0 out of 5 average rating, 3 reviewsLakeside 3-BR Berkshires Residence
Nov. 11 – 18
Home in Great Barrington
4.97 out of 5 average rating, 38 reviewsWaterfront Modern Lake Mansfield Retreat
Feb. 20 – 27
Home in Great Barrington
5.0 out of 5 average rating, 3 reviewsWalt's Townhouse - Berkshire living at its best
Nov. 10 – 17
Home in Becket
4.85 out of 5 average rating, 33 reviewsPrivate Cabin On Over 12 Acres Of Woods!
Oct. 27 – Nov. 3
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