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 Lanesborough
5 out of 5 average rating, 12 reviewsBerkshire Mountain House
Home in Egremont
5 out of 5 average rating, 16 reviewsThe Catamount Haus w. Pool/Hot Tub
Home in Pittsfield
4.98 out of 5 average rating, 50 reviewsBerkshire Lakefront Home W/Pool-100%Renovated
Home in Great Barrington
4.98 out of 5 average rating, 61 reviewsStunning luxury home with fire pit
Home in Canaan
4.99 out of 5 average rating, 83 reviewsBerkshire Lake House, gunite pool, Chef's Kitchen
Home in Hillsdale
4.89 out of 5 average rating, 27 reviewsHilltop: Panoramic Views w/ Pool near Catamount
Home in East Chatham
5 out of 5 average rating, 7 reviewsStylish Rural Sanctuary
Home in Canaan
4.67 out of 5 average rating, 63 reviewsR3Bliss - Estate with Hot Tub, Tennis Court & Pool
Weekly house rentals
Home in Canaan
4.95 out of 5 average rating, 38 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, 92 reviewsMountain View Hideaway
Home in West Stockbridge
5 out of 5 average rating, 41 reviewsBerkshires Forest Retreat with Hot Tub
Home in Becket
5 out of 5 average rating, 29 reviewsBerkshires Lakefront Stylish Retreat w/Gameroom
Home in Great Barrington
4.99 out of 5 average rating, 96 reviewsGranite Ledge, Modern home in a unique setting
Home in Becket
5 out of 5 average rating, 28 reviewsBerkshires Retreat! Hiking, Hot Tub, Outlets
Home in West Stockbridge
5 out of 5 average rating, 32 reviewsBeautiful And Private Home Centrally Located
Private house rentals
Home in Great Barrington
4.98 out of 5 average rating, 45 reviewsWaterfront Modern Lake Mansfield Retreat
Home in Becket
4.92 out of 5 average rating, 74 reviewsLittle Longbow Lakefront Chalet
Home in Sandisfield
5 out of 5 average rating, 29 reviewsWaterfront oasis in heart of Berkshires
Home in Egremont
4.93 out of 5 average rating, 72 reviewsModern and Stylish Country Lakeside Cottage
Home in Lanesborough
4.96 out of 5 average rating, 96 reviewsBerkshire Bliss- 6BR/Minutes from Jiminy +38 acres
Home in Great Barrington
4.98 out of 5 average rating, 43 reviewsRenovated Downtown Great Barrington House
Home in Becket
4.81 out of 5 average rating, 48 reviewsPrivate Cabin On Over 12 Acres Of Woods!
Home in Lenox
5 out of 5 average rating, 18 reviewsLakefront Retreat -Private Dock,creek,and Fire pit
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