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, 325 reviewsGoose Landing Cottage by the lake with NEW Hot Tub
Cottage in Woodstock
4.9 out of 5 average rating, 376 reviewsFamous Architect - Streamside Cottage w/ hot tub
Cottage in Litchfield
4.89 out of 5 average rating, 261 reviewsLitchfield - Hot Tub - Mohawk Mountain - Fireplace
Cottage in Phoenicia
4.89 out of 5 average rating, 805 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, 142 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 Sharon
4.9 out of 5 average rating, 126 reviewsFoxfire Hill: A Bit of Luxury in the Countryside
Cottage in Catskill
4.96 out of 5 average rating, 233 reviews1930's Cottage charm air conditioned near hiking
Cottage in Gilboa
4.94 out of 5 average rating, 203 reviewsHome Alone Mountain Retreat
Cottage in Williamstown
4.9 out of 5 average rating, 165 reviewsCute Cozy Comfy Cottage in the Berkshires
Cottage in Hillsdale
4.94 out of 5 average rating, 171 reviewsCozy Cottage Catamount, Berkshires Walk to Brewery
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, 413 reviewsSun Cottage- "A view with a room(s)."
Cottage in Orange
4.96 out of 5 average rating, 202 reviewsThe Fishing Cottage: A Sweetwater Stay
Private cottage rentals
Cottage in Chichester
4.99 out of 5 average rating, 514 reviewsGarden Cottage In The Catskills
Cottage in Valatie
4.99 out of 5 average rating, 127 reviewsKinderhook Lake Retreat-private+kayaks/sup+swim+ac
Cottage in Copake Falls
4.91 out of 5 average rating, 320 reviewsBeautiful cottage at the foot of the Birkshires
Cottage in Saugerties
4.93 out of 5 average rating, 218 reviewsNew:Cozy Barn-Style Retreat Minutes From Woodstock
Cottage in West Stockbridge
4.98 out of 5 average rating, 108 reviewsHistoric 1810 Farmhouse - Fully Renovated
Cottage in Ashfield
4.97 out of 5 average rating, 302 reviewshope house
Cottage in Saugerties
5.0 out of 5 average rating, 316 reviewsCarriage House on Falls, Walk to Village
Cottage in Kerhonkson
4.94 out of 5 average rating, 258 reviewsBlue Haven in the Catskills
Destinations to explore
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