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 Woodstock
4.9 out of 5 average rating, 377 reviewsFamous Architect - Streamside Cottage w/ hot tub
Cottage in Litchfield
4.89 out of 5 average rating, 263 reviewsLitchfield - Hot Tub - Mohawk Mountain - Fireplace
Cottage in Red Hook
4.92 out of 5 average rating, 326 reviewsGoose Landing Cottage by the lake with NEW Hot Tub
Cottage in Phoenicia
4.89 out of 5 average rating, 807 reviewsRomantic hot tub cottage. Hiking/breweries nearby.
Cottage in Guilford
4.96 out of 5 average rating, 161 reviewsLuxury cottage by the sea with hot tub and pool
Cottage in Denver
4.96 out of 5 average rating, 110 reviewsCountry Cottage w/ HOT TUB & Views
Cottage in Kerhonkson
4.85 out of 5 average rating, 143 reviewsGunks Cottage|Fire Pit|Pool|Near Minnewaska Park
Cottage in West Hurley
4.94 out of 5 average rating, 251 reviewsWoodstock Carriage House HotTub FirePit Pool
Pet-friendly cottage rentals
Cottage in Williamstown
4.9 out of 5 average rating, 165 reviewsCute Cozy Comfy Cottage in the Berkshires
Cottage in Gilboa
4.94 out of 5 average rating, 203 reviewsHome Alone Mountain Retreat
Cottage in Claverack
4.98 out of 5 average rating, 247 reviews‘Clavashack’ Country Cottage
Cottage in Saugerties
4.93 out of 5 average rating, 221 reviewsChic & Cozy Cottage 10 mins to Woodstock
Cottage in Orange
4.94 out of 5 average rating, 133 reviewsThe Lake Cottage: A Sweetwater Stay
Cottage in Bloomington
4.98 out of 5 average rating, 470 reviews'The Blue Jay Cottage' - Privacy With A View!
Cottage in High Falls
4.99 out of 5 average rating, 414 reviewsSun Cottage- "A view with a room(s)."
Cottage in Sharon
4.91 out of 5 average rating, 127 reviewsFoxfire Hill: A Bit of Luxury in the Countryside
Private cottage rentals
Cottage in Chichester
4.99 out of 5 average rating, 515 reviewsGarden Cottage In The Catskills
Cottage in Copake Falls
4.91 out of 5 average rating, 320 reviewsBeautiful cottage at the foot of the Birkshires
Cottage in Valatie
4.99 out of 5 average rating, 127 reviewsKinderhook Lake Retreat-private+kayaks/sup+swim+ac
Cottage in Hillsdale
4.83 out of 5 average rating, 235 reviewsBig Bliss Near Catamount Cottage w/Modern Flair
Cottage in Roxbury
4.98 out of 5 average rating, 483 reviewsThe Little House
Cottage in Ashfield
4.97 out of 5 average rating, 302 reviewshope house
Cottage in Accord
4.88 out of 5 average rating, 218 reviewsSweet Cottage on a Farm Road
Cottage in Collinsville
4.96 out of 5 average rating, 113 reviewsThe Carriage House
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