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
5.0 out of 5 average rating, 11 reviewsNorte Maison 2 beds 2 Baths Minutes to Jiminy Peak
May 8 – 15
Cottage in Great Barrington
4.84 out of 5 average rating, 25 reviewsTHE GREAT ESCAPE BERKSHIRE SKI COTTAGE w/HOT TUB!
Jun 17 – 24
Cottage in Monterey
4.88 out of 5 average rating, 8 reviewsmountain refuge
May 9 – 16
Cottage in Otis
4.96 out of 5 average rating, 28 reviewsBerkshire lakefront cabin with modern luxuries
May 8 – 15
Cottage in Becket
4.6 out of 5 average rating, 144 reviewsA Magical Spot on Little Robin Lake
Sep 1 – 8
Pet-friendly cottage rentals
Cottage in Great Barrington
4.88 out of 5 average rating, 42 reviewsCarriage house with Chef's Kitchen, close to town
Dec 26 – Jan 2
Cottage in Becket
4.76 out of 5 average rating, 139 reviewsPrivate Lake Cottage on 3 acres w/350 sq. ft. deck
Dec 10 – 17
Cottage in Spencertown
5.0 out of 5 average rating, 26 reviewsRock Haven Cottage
Feb 2 – 9
Cottage in Becket
5.0 out of 5 average rating, 13 reviewsCheerful 3+ bedroom cottage with lake views
Jan 22 – 29
Cottage in Austerlitz
4.94 out of 5 average rating, 50 reviewsHarvey Mountain Lodge by State Forest
Oct 18 – 25
Cottage in Monterey
5.0 out of 5 average rating, 18 reviewsHistoric Berkshires Cottage with a View
May 24 – 31
Cottage in Austerlitz
5.0 out of 5 average rating, 6 reviewsCozy Berkshire Cottage
Jun 4 – 11
Cottage in New Lebanon
4.88 out of 5 average rating, 42 reviewsCozy Cottage in the Clouds With Mountain Views
Feb 4 – 11
Private cottage rentals
Cottage in Becket
4.87 out of 5 average rating, 75 reviewsStylish Shales Brook Cottage-Cozy up to happiness
Jan 17 – 24
Cottage in Williamstown
4.97 out of 5 average rating, 72 reviewsArtistic Nature Cottage
Apr 14 – 21
Cottage in Sheffield
5.0 out of 5 average rating, 17 reviewsThe Blue Elm - A Historic Country Cottage
Nov 2 – 9
Cottage in Lanesborough
4.98 out of 5 average rating, 46 reviewsAmazing 2 bedroom lake front cottage, large patio
Nov 20 – 27
Cottage in Monterey
5.0 out of 5 average rating, 35 reviewsBeaver Lodge
Nov 17 – 24
Cottage in Stockbridge
5.0 out of 5 average rating, 21 reviewsQuiet 2 BR cottage in the heart of the Berkshires
Sep 10 – 17
Cottage in Pittsfield
5.0 out of 5 average rating, 82 reviewsCozy Berkshire cottage with indoor fireplace
Apr 4 – 11
Cottage in Great Barrington
4.73 out of 5 average rating, 56 reviewsSunny Cottage with fireplace in the Berkshires
Aug 1 – 8
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