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 Red Hook
4.92 out of 5 average rating, 324 reviewsGoose Landing Cottage by the lake with NEW Hot Tub
Dec 2 – 9
Cottage in Phoenicia
4.89 out of 5 average rating, 802 reviewsRomantic hot tub cottage. Hiking/breweries nearby.
Sep 5 – 12
Cottage in Woodstock
4.9 out of 5 average rating, 376 reviewsFamous Architect - Streamside Cottage w/ hot tub
Sep 27 – Oct 4
Cottage in Kent
4.88 out of 5 average rating, 153 reviewsNEW - Hot Tub - Mohawk Mtn - Appalachian Trl
Dec 13 – 20
Cottage in Guilford
4.96 out of 5 average rating, 158 reviewsLuxury cottage by the sea with hot tub and pool
Dec 3 – 10
Cottage in Denver
4.96 out of 5 average rating, 110 reviewsCountry Cottage w/ HOT TUB & Views
Jun 18 – 25
Cottage in Highland Lakes
4.97 out of 5 average rating, 268 reviewsThe Mountaintop Lakehouse that Time Forgot.
Dec 30 – Jan 6
Cottage in Kerhonkson
4.84 out of 5 average rating, 141 reviewsGunks Cottage|Fire Pit|Pool|Near Minnewaska Park
Aug 26 – Sep 2
Pet-friendly cottage rentals
Cottage in Granby
4.87 out of 5 average rating, 138 reviewsThe Little Red Schoolhouse ~ Circa 1877
Apr 10 – 17
Cottage in Florida
4.82 out of 5 average rating, 102 reviewsPeaceful Mountain Cabin by Ski, Kayak, Museums +!
Dec 11 – 18
Cottage in Gilboa
4.94 out of 5 average rating, 201 reviewsHome Alone Mountain Retreat
Nov 6 – 13
Cottage in Claverack
4.98 out of 5 average rating, 244 reviews‘Clavashack’ Country Cottage
Aug 18 – 23
Cottage in Catskill
4.96 out of 5 average rating, 233 reviews1930's Cottage charm air conditioned near hiking
Sep 23 – 30
Cottage in Orange
4.95 out of 5 average rating, 198 reviewsThe Fishing Cottage: A Sweetwater Stay
Jan 31 – Feb 7
Cottage in Hillsdale
4.94 out of 5 average rating, 171 reviewsCozy Cottage Catamount, Berkshires Walk to Brewery
Mar 12 – 19
Cottage in Dover
4.95 out of 5 average rating, 216 reviewsCozy summer cottage in the woods of southern VT
May 30 – Jun 6
Private cottage rentals
Cottage in Copake Falls
4.91 out of 5 average rating, 317 reviewsBeautiful cottage at the foot of the Birkshires
Jan 11 – 18
Cottage in Saugerties
4.93 out of 5 average rating, 217 reviewsNew:Cozy Barn-Style Retreat Minutes From Woodstock
Oct 6 – 13
Cottage in Chichester
4.99 out of 5 average rating, 514 reviewsGarden Cottage In The Catskills
Sep 25 – Oct 2
Cottage in Rhinebeck
4.99 out of 5 average rating, 121 reviewsFabulous Lemon Cottage in Rhinebeck, NY
Oct 23 – 30
Cottage in Collinsville
4.96 out of 5 average rating, 112 reviewsThe Carriage House
Oct 31 – Nov 7
Cottage in Saugerties
5.0 out of 5 average rating, 314 reviewsCarriage House on Falls, Walk to Village
Oct 10 – 17
Cottage in Greenwood Lake
4.97 out of 5 average rating, 281 reviewsLuxury Cottage with Spectacular Lake Views
Nov 8 – 15
Cottage in Rosendale
4.99 out of 5 average rating, 123 reviewsSweet Green Rosendale Cottage
Oct 3 – 10
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