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 7 – 14
Cottage in Great Barrington
4.84 out of 5 average rating, 25 reviewsTHE GREAT ESCAPE BERKSHIRE SKI COTTAGE w/HOT TUB!
Nov 16 – 23
Cottage in Monterey
4.88 out of 5 average rating, 8 reviewsmountain refuge
May 8 – 15
Cottage in Otis
4.96 out of 5 average rating, 28 reviewsBerkshire lakefront cabin with modern luxuries
Jun 16 – 23
Cottage in Becket
4.6 out of 5 average rating, 144 reviewsA Magical Spot on Little Robin Lake
Sep 21 – 28
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 Austerlitz
4.94 out of 5 average rating, 50 reviewsHarvey Mountain Lodge by State Forest
Jun 11 – 18
Cottage in Spencertown
5.0 out of 5 average rating, 26 reviewsRock Haven Cottage
Apr 14 – 21
Cottage in Monterey
5.0 out of 5 average rating, 18 reviewsHistoric Berkshires Cottage with a View
Oct 9 – 16
Cottage in Becket
5.0 out of 5 average rating, 13 reviewsCheerful 3+ bedroom cottage with lake views
Sep 12 – 19
Cottage in Austerlitz
5.0 out of 5 average rating, 6 reviewsCozy Berkshire Cottage
May 12 – 19
Cottage in New Lebanon
4.88 out of 5 average rating, 42 reviewsCozy Cottage in the Clouds With Mountain Views
Jul 10 – 17
Private cottage rentals
Cottage in Williamstown
4.97 out of 5 average rating, 72 reviewsArtistic Nature Cottage
Feb 6 – 13
Cottage in Becket
4.87 out of 5 average rating, 75 reviewsStylish Shales Brook Cottage-Cozy up to happiness
Dec 22 – 29
Cottage in Sheffield
5.0 out of 5 average rating, 17 reviewsThe Blue Elm - A Historic Country Cottage
Jun 16 – 23
Cottage in Monterey
5.0 out of 5 average rating, 35 reviewsBeaver Lodge
Dec 23 – 30
Cottage in Lanesborough
4.98 out of 5 average rating, 46 reviewsAmazing 2 bedroom lake front cottage, large patio
Feb 4 – 11
Cottage in Stockbridge
5.0 out of 5 average rating, 21 reviewsQuiet 2 BR cottage in the heart of the Berkshires
Jun 13 – 20
Cottage in Pittsfield
5.0 out of 5 average rating, 81 reviewsCozy Berkshire cottage with indoor fireplace
Apr 3 – 10
Cottage in Great Barrington
4.73 out of 5 average rating, 56 reviewsSunny Cottage with fireplace in the Berkshires
Sep 24 – Oct 1
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