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 Egremont
5 out of 5 average rating, 13 reviewsThe Catamount Haus w. Pool/Hot Tub
Home in Pittsfield
4.98 out of 5 average rating, 47 reviewsBerkshire Lakefront Home W/Pool-100%Renovated
Home in Great Barrington
5 out of 5 average rating, 58 reviewsStunning luxury home with pool
Home in Great Barrington
4.93 out of 5 average rating, 40 reviewsBerkshire Country Estate! Pool & Tennis Court -GB
Home in Cheshire
4.93 out of 5 average rating, 67 reviewsBerkshire County modern home + pool
Home in Sheffield
4.95 out of 5 average rating, 21 reviewsPrivate Berkshire County Retreat
Home in Great Barrington
4.75 out of 5 average rating, 4 reviewsStylish Retreat; Pool & Hot Tub By:Evergreen Home
Home in New Marlborough
4.97 out of 5 average rating, 29 reviewsBerkshires Colonial Farmhouse
Weekly house rentals
Home in Canaan
4.97 out of 5 average rating, 32 reviewsOn Lillie Pond: A Private Woods Retreat
Home in Sandisfield
5 out of 5 average rating, 25 reviewsWaterfront oasis in heart of Berkshires
Home in Richmond
5 out of 5 average rating, 65 reviewsLUXURY BERKSHIRES BARN! GRAND! VIEWS! 2/2
Home in Becket
4.96 out of 5 average rating, 23 reviewsNew Shaw Pond Skytop Retreat in the Berkshires
Home in Becket
5 out of 5 average rating, 22 reviewsBerkshires Lakefront Stylish Retreat w/Gameroom
Home in Great Barrington
5 out of 5 average rating, 43 reviewsThe Yellow Victorian With Chefs Kitchen
Home in Great Barrington
4.99 out of 5 average rating, 83 reviewsGranite Ledge, Modern home in a unique setting
Home in West Stockbridge
5 out of 5 average rating, 26 reviewsBeautiful And Private Home Centrally Located
Private house rentals
Home in Adams
4.89 out of 5 average rating, 85 reviewsMountain View Hideaway
Home in Canaan
5 out of 5 average rating, 37 reviewsNEW! Berkshires Farmhouse w/ Firepit & Wood Stove
Home in West Stockbridge
5 out of 5 average rating, 36 reviewsBerkshires Forest Retreat with Hot Tub
Home in Great Barrington
5 out of 5 average rating, 76 reviewsPrivate Home in The Berkshires (New Hot Tub!)
Home in Great Barrington
4.95 out of 5 average rating, 20 reviewsCharming Cottage - Walk To Town
Home in Lee
4.95 out of 5 average rating, 19 reviewsRiver Front Cottage
Home in Otis
4.9 out of 5 average rating, 42 reviewsBerkshire Lakefront Lighthouse Getaway
Home in Cheshire
5 out of 5 average rating, 40 reviewsThe Berkshires Hummingbird House
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