Cottage vacation rentals in The Berkshires
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Top-rated cottage rentals in The Berkshires
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 The Berkshires cottage rentals
Cottage rentals with a hot tub
Cottage in Shaftsbury
4.99 out of 5 average rating, 601 reviewsVermont Schoolhouse Farm Cottage - Sauna + Hot Tub
Feb 20 – 27
Cottage in Red Hook
4.92 out of 5 average rating, 324 reviewsGoose Landing Cottage by the lake with NEW Hot Tub
Apr 27 – May 4
Cottage in Woodstock
4.9 out of 5 average rating, 376 reviewsFamous Architect - Streamside Cottage w/ hot tub
Sep 14 – 21
Cottage in Phoenicia
4.89 out of 5 average rating, 804 reviewsRomantic hot tub cottage. Hiking/breweries nearby.
Oct 17 – 24
Cottage in Kent
4.88 out of 5 average rating, 153 reviewsNEW - Hot Tub - Mohawk Mtn - Appalachian Trl
Mar 17 – 24
Cottage in Guilford
4.96 out of 5 average rating, 159 reviewsLuxury cottage by the sea with hot tub and pool
Apr 22 – 29
Cottage in Denver
4.96 out of 5 average rating, 110 reviewsCountry Cottage w/ HOT TUB & Views
Jun 24 – Jul 1
Cottage in Kerhonkson
4.85 out of 5 average rating, 142 reviewsGunks Cottage|Fire Pit|Pool|Near Minnewaska Park
Nov 10 – 17
Pet-friendly cottage rentals
Cottage in Florida
4.82 out of 5 average rating, 102 reviewsPeaceful Mountain Cabin by Ski, Kayak, Museums +!
Apr 7 – 14
Cottage in Granby
4.87 out of 5 average rating, 138 reviewsThe Little Red Schoolhouse ~ Circa 1877
Apr 3 – 10
Cottage in Catskill
4.96 out of 5 average rating, 233 reviews1930's Cottage charm air conditioned near hiking
Nov 6 – 13
Cottage in Sharon
4.9 out of 5 average rating, 125 reviewsFoxfire Hill: A Bit of Luxury in the Countryside
Oct 2 – 9
Cottage in Gilboa
4.94 out of 5 average rating, 201 reviewsHome Alone Mountain Retreat
Sep 16 – 23
Cottage in Orange
4.95 out of 5 average rating, 199 reviewsThe Fishing Cottage: A Sweetwater Stay
Jan 19 – 26
Cottage in Hillsdale
4.94 out of 5 average rating, 171 reviewsCozy Cottage Catamount, Berkshires Walk to Brewery
Jul 13 – 20
Cottage in Sheffield, The Berkshires
4.93 out of 5 average rating, 105 reviewsCheerful 3-bedroom cottage with woodstove.
Jan 17 – 24
Private cottage rentals
Cottage in Chichester
4.99 out of 5 average rating, 514 reviewsGarden Cottage In The Catskills
Aug 17 – 24
Cottage in Saugerties
4.93 out of 5 average rating, 218 reviewsNew:Cozy Barn-Style Retreat Minutes From Woodstock
Oct 6 – 13
Cottage in Valatie
4.99 out of 5 average rating, 127 reviewsKinderhook Lake Retreat-private+kayaks/sup+swim+ac
Sep 8 – 15
Cottage in Collinsville
4.96 out of 5 average rating, 113 reviewsThe Carriage House
Sep 27 – Oct 4
Cottage in Kerhonkson
4.94 out of 5 average rating, 257 reviewsBlue Haven in the Catskills
Sep 12 – 19
Cottage in Woodstock
4.99 out of 5 average rating, 278 reviewsGrapevine Cottage
Apr 15 – 22
Cottage in Roxbury
4.98 out of 5 average rating, 482 reviewsThe Little House
Feb 19 – 26
Cottage in Rhinebeck
4.99 out of 5 average rating, 121 reviewsFabulous Lemon Cottage in Rhinebeck, NY
Jul 15 – 22
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