Cottage vacation rentals in Berkshire County
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Top-rated cottage rentals in Berkshire County
Guests agree: these cottages are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Berkshire County cottage rentals
Cottage rentals with a hot tub
Cottage in Lanesborough
5 out of 5 average rating, 11 reviewsNorte Maison 2 beds 2 Baths Minutes to Jiminy Peak
Cottage in Great Barrington
4.85 out of 5 average rating, 26 reviewsTHE GREAT ESCAPE BERKSHIRE SKI COTTAGE w/HOT TUB!
Cottage in Monterey
4.88 out of 5 average rating, 8 reviewsmountain refuge
Cottage in Otis
4.97 out of 5 average rating, 29 reviewsBerkshire lakefront cabin with modern luxuries
Cottage in Becket
4.61 out of 5 average rating, 145 reviewsA Magical Spot on Little Robin Lake
Pet-friendly cottage rentals
Cottage in Pittsfield
4.9 out of 5 average rating, 69 reviewsCottage Getaway - access all the Berkshires offer!
Cottage in Austerlitz
4.94 out of 5 average rating, 52 reviewsHarvey Mountain Lodge by State Forest
Cottage in Becket
4.76 out of 5 average rating, 142 reviewsPrivate Lake Cottage on 3 acres w/350 sq. ft. deck
Cottage in Great Barrington
4.89 out of 5 average rating, 47 reviewsCarriage house with Chef's Kitchen, close to town
Cottage in Monterey
5 out of 5 average rating, 19 reviewsHistoric Berkshires Cottage with a View
Cottage in Spencertown
5 out of 5 average rating, 27 reviewsRock Haven Cottage
Cottage in Becket
5 out of 5 average rating, 14 reviewsCheerful 3+ bedroom cottage with lake views
Cottage in New Lebanon
4.89 out of 5 average rating, 44 reviewsCozy Cottage in the Clouds With Mountain Views
Private cottage rentals
Cottage in Becket
4.87 out of 5 average rating, 77 reviewsStylish Shales Brook Cottage-Cozy up to happiness
Cottage in Sheffield
5 out of 5 average rating, 22 reviewsThe Blue Elm - A Historic Country Cottage
Cottage in Williamstown
4.97 out of 5 average rating, 76 reviewsArtistic Nature Cottage
Cottage in Lanesborough
4.98 out of 5 average rating, 48 reviewsAmazing 2 bedroom lake front cottage, large patio
Cottage in Stockbridge
4.96 out of 5 average rating, 24 reviewsQuiet 2 BR cottage in the heart of the Berkshires
Cottage in Monterey
5 out of 5 average rating, 38 reviewsBeaver Lodge
Cottage in Great Barrington
4.74 out of 5 average rating, 58 reviewsSunny Cottage with fireplace in the Berkshires
Cottage in Pittsfield
5 out of 5 average rating, 85 reviewsCozy Berkshire cottage with indoor fireplace
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