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Cottage vacation rentals in Berkshire County
Find and book unique cottages on Airbnb
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
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Cottage in Lanesborough
5 out of 5 average rating, 11 reviewsNorte Maison 2 beds 2 Baths Minutes to Jiminy Peak
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Cottage in Great Barrington
4.85 out of 5 average rating, 26 reviewsTHE GREAT ESCAPE BERKSHIRE SKI COTTAGE w/HOT TUB!
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Cottage in Monterey
4.88 out of 5 average rating, 8 reviewsmountain refuge
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Cottage in Becket
4.61 out of 5 average rating, 146 reviewsA Magical Spot on Little Robin Lake
Pet-friendly cottage rentals
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Cottage in Williamstown
4.74 out of 5 average rating, 61 reviewsPet friendly, cozy, modest cape, two bedrooms
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Cottage in Austerlitz
4.93 out of 5 average rating, 54 reviewsHarvey Mountain Lodge by State Forest
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Cottage in Becket
4.76 out of 5 average rating, 142 reviewsPrivate Lake Cottage on 3 acres w/350 sq. ft. deck
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Cottage in Monterey
5 out of 5 average rating, 19 reviewsHistoric Berkshires Cottage with a View
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Cottage in New Lebanon
4.89 out of 5 average rating, 44 reviewsCozy Cottage in the Clouds With Mountain Views
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Cottage in Becket
5 out of 5 average rating, 14 reviewsCheerful 3+ bedroom cottage with lake views
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Cottage in Great Barrington
4.89 out of 5 average rating, 47 reviewsCarriage house with Chef's Kitchen, close to town
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Cottage in Spencertown
5 out of 5 average rating, 27 reviewsRock Haven Cottage
Private cottage rentals
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Cottage in Becket
4.87 out of 5 average rating, 78 reviewsStylish Shales Brook Cottage-Cozy up to happiness
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Cottage in Sheffield
5 out of 5 average rating, 23 reviewsThe Blue Elm - A Historic Country Cottage
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Cottage in Williamstown
4.97 out of 5 average rating, 77 reviewsArtistic Nature Cottage
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Cottage in Lanesborough
4.98 out of 5 average rating, 49 reviewsAmazing 2 bedroom lake front cottage, large patio
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Cottage in Stockbridge
4.96 out of 5 average rating, 24 reviewsQuiet 2 BR cottage in the heart of the Berkshires
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Cottage in Monterey
5 out of 5 average rating, 39 reviewsBeaver Lodge
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Cottage in Great Barrington
4.75 out of 5 average rating, 59 reviewsSunny Cottage with fireplace in the Berkshires
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Cottage in Pittsfield
4.79 out of 5 average rating, 29 reviewsCharming lakeview cottage w/ kayaks, Richmond Pond
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