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 Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
Home in Pittsfield
4.96 out of 5 average rating, 56 reviewsBerkshire Getaway Ranch 3 acres + saltwater pool
Home in Cheshire
4.94 out of 5 average rating, 52 reviewsBerkshire County modern home + pool
Home in Great Barrington
4.97 out of 5 average rating, 34 reviewsBerkshire Country Estate! Pool & Tennis Court -GB
Home in Sheffield
4.94 out of 5 average rating, 16 reviewsPrivate Berkshire County Retreat
Home in Egremont
5.0 out of 5 average rating, 3 reviewsCatamount House w. Pool/Hot Tub
Home in West Stockbridge
5.0 out of 5 average rating, 18 reviewsBerkshire House on the Hill
Home in Pittsfield
5.0 out of 5 average rating, 43 reviewsStunning Berkshires Retreat, Large and Private
Weekly house rentals
Home in Lenox
4.93 out of 5 average rating, 213 reviewsHeart of Lenox Walk to Town Cozy Cottage!
Home in Canaan
4.9 out of 5 average rating, 150 reviewsBerkshire Lakefront House with Amazing Views
Home in Egremont
4.96 out of 5 average rating, 106 reviewsThe Berkshires Mountain Terrace LUX Home Sleeps 7
Home in Becket
4.86 out of 5 average rating, 294 reviewsReal Estate:Therapy - Lake, Laundry, Love it
Home in Sheffield
4.93 out of 5 average rating, 111 reviewsA Private Peninsula Retreat In The Berkshires!
Home in New Marlborough
4.89 out of 5 average rating, 122 reviewsLake House in the Berkshire (Access Dock & Canoe
Home in Egremont
4.97 out of 5 average rating, 113 reviewsA sunny, quiet chalet beautifully decorated.
Home in Becket
4.95 out of 5 average rating, 41 reviewsNerd Preservation Sanctuary
Private house rentals
Home in Adams
4.92 out of 5 average rating, 74 reviewsMountain View Hideaway
Home in Great Barrington
4.98 out of 5 average rating, 41 reviewsSunsets On Blue Hill, Newly Renovated Farmhouse
Home in Becket
5.0 out of 5 average rating, 9 reviewsLakeside 3-BR Berkshires Residence
Home in Great Barrington
4.97 out of 5 average rating, 38 reviewsWaterfront Modern Lake Mansfield Retreat
Home in Pittsfield
4.97 out of 5 average rating, 36 reviewsCharming lake house with amazing sunset views
Home in Great Barrington
5.0 out of 5 average rating, 7 reviewsWalt's Townhouse - Berkshire living at its best
Home in Great Barrington
4.93 out of 5 average rating, 68 reviewsQuiet home on the hill.
Home in West Stockbridge
5.0 out of 5 average rating, 19 reviewsBeautiful And Private Home Centrally Located
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