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
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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 4 – 11
Cottage in Great Barrington
4.84 out of 5 average rating, 25 reviewsTHE GREAT ESCAPE BERKSHIRE SKI COTTAGE w/HOT TUB!
Nov. 13 – 20
Cottage in Monterey
4.88 out of 5 average rating, 8 reviewsmountain refuge
Sep. 10 – 17
Cottage in Otis
4.96 out of 5 average rating, 28 reviewsBerkshire lakefront cabin with modern luxuries
Jun. 15 – 22
Cottage in Becket
4.6 out of 5 average rating, 144 reviewsA Magical Spot on Little Robin Lake
Jun. 5 – 12
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
Nov. 3 – 10
Cottage in Becket
4.76 out of 5 average rating, 139 reviewsPrivate Lake Cottage on 3 acres w/350 sq. ft. deck
Jan. 20 – 27
Cottage in Austerlitz
4.94 out of 5 average rating, 50 reviewsHarvey Mountain Lodge by State Forest
Jun. 8 – 15
Cottage in Austerlitz
5.0 out of 5 average rating, 6 reviewsCozy Berkshire Cottage
Jun. 14 – 21
Cottage in Spencertown
5.0 out of 5 average rating, 25 reviewsRock Haven Cottage
Sep. 14 – 21
Cottage in Monterey
5.0 out of 5 average rating, 18 reviewsHistoric Berkshires Cottage with a View
May 16 – 23
Cottage in Becket
5.0 out of 5 average rating, 13 reviewsCheerful 3+ bedroom cottage with lake views
Jul. 27 – Aug. 3
Cottage in Williamstown
4.71 out of 5 average rating, 56 reviewsPet friendly, cozy, modest cape, two bedrooms
Nov. 19 – 26
Private cottage rentals
Cottage in Becket
4.87 out of 5 average rating, 75 reviewsStylish Shales Brook Cottage-Cozy up to happiness
Feb. 2 – 9
Cottage in Williamstown
4.97 out of 5 average rating, 72 reviewsArtistic Nature Cottage
Nov. 5 – 12
Cottage in Monterey
5.0 out of 5 average rating, 35 reviewsBeaver Lodge
Dec. 20 – 27
Cottage in Stockbridge
5.0 out of 5 average rating, 21 reviewsQuiet 2 BR cottage in the heart of the Berkshires
May 5 – 12
Cottage in Lanesborough
4.98 out of 5 average rating, 46 reviewsAmazing 2 bedroom lake front cottage, large patio
Nov. 23 – 30
Cottage in Sheffield
5.0 out of 5 average rating, 17 reviewsThe Blue Elm - A Historic Country Cottage
Sep. 25 – Oct. 2
Cottage in Pittsfield
5.0 out of 5 average rating, 81 reviewsCozy Berkshire cottage with indoor fireplace
Jan. 27 – Feb. 3
Cottage in Hinsdale
4.97 out of 5 average rating, 68 reviewsBerkshires - Charming Lakefront Cottage
Apr. 21 – 28
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