House holiday 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.
Holiday rentals for every style
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Popular amenities for house rentals in Berkshire County
House rentals with a pool
Home in Otis
4.91 out of 5 average rating, 11 reviewsBerkshires Oasis Retreat: Art Meets Nature
Home in West Stockbridge
4.97 out of 5 average rating, 69 reviewsPanoramic Views, Indoor Pool by Evergreen Home
Home in Lanesborough
5 out of 5 average rating, 12 reviewsBerkshire Mountain House
Home in Egremont
5 out of 5 average rating, 15 reviewsThe Catamount Haus w. Pool/Hot Tub
Home in Hancock
5 out of 5 average rating, 13 reviewsBougie B's Mountainside Getaway
Home in Pittsfield
4.98 out of 5 average rating, 49 reviewsBerkshire Lakefront Home W/Pool-100%Renovated
Home in Great Barrington
4.98 out of 5 average rating, 60 reviewsStunning luxury home with fire pit
Home in Canaan
4.99 out of 5 average rating, 82 reviewsBerkshire Lake House, gunite pool, Chef's Kitchen
Weekly house rentals
Home in Canaan
4.94 out of 5 average rating, 36 reviewsOn Lillie Pond: A Private Woods Retreat
Home in Becket
4.95 out of 5 average rating, 65 reviewsNerd Preservation Sanctuary
Home in Adams
4.9 out of 5 average rating, 90 reviewsMountain View Hideaway
Home in Sandisfield
5 out of 5 average rating, 29 reviewsWaterfront oasis in heart of Berkshires
Home in Becket
5 out of 5 average rating, 26 reviewsBerkshires Lakefront Stylish Retreat w/Gameroom
Home in Great Barrington
5 out of 5 average rating, 34 reviewsLovers Lane. Hot tub, fire pit, mtn view, dogs ok
Home in Great Barrington
4.99 out of 5 average rating, 91 reviewsGranite Ledge, Modern home in a unique setting
Home in West Stockbridge
5 out of 5 average rating, 30 reviewsBeautiful And Private Home Centrally Located
Private house rentals
Home in Becket
4.91 out of 5 average rating, 70 reviewsLittle Longbow Lakefront Chalet
Home in West Stockbridge
5 out of 5 average rating, 39 reviewsBerkshires Forest Retreat with Hot Tub
Home in Great Barrington
5 out of 5 average rating, 22 reviewsSki Season rental with views of Butternut Ski Area
Home in Great Barrington
4.99 out of 5 average rating, 84 reviewsPrivate Home in The Berkshires (New Hot Tub!)
Home in Great Barrington
5 out of 5 average rating, 44 reviewsThe Yellow Victorian With Chefs Kitchen
Home in Cheshire
5 out of 5 average rating, 45 reviewsThe Berkshires Hummingbird House
Home in Great Barrington
4.98 out of 5 average rating, 42 reviewsRenovated Downtown Great Barrington House
Home in Becket
4.93 out of 5 average rating, 69 reviewsTranquil 3-BR Waterfront Retreat
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