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 Great Barrington
4.93 out of 5 average rating, 239 reviewsArtist Cottage
Cottage in Shaftsbury
4.99 out of 5 average rating, 606 reviewsVermont Schoolhouse Farm Cottage - Sauna + Hot Tub
Cottage in Woodstock
4.9 out of 5 average rating, 378 reviewsFamous Architect - Streamside Cottage w/ hot tub
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, 809 reviewsRomantic hot tub cottage. Hiking/breweries nearby.
Cottage in Litchfield
4.89 out of 5 average rating, 263 reviewsLitchfield - Hot Tub - Mohawk Mountain - Fireplace
Cottage in Guilford
4.96 out of 5 average rating, 162 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
Pet-friendly cottage rentals
Cottage in Catskill
4.96 out of 5 average rating, 233 reviews1930's Cottage charm air conditioned near hiking
Cottage in Claverack
4.98 out of 5 average rating, 247 reviews‘Clavashack’ Country Cottage
Cottage in Williamstown
4.9 out of 5 average rating, 166 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, 473 reviews'The Blue Jay Cottage' - Privacy With A View!
Cottage in High Falls
4.99 out of 5 average rating, 416 reviewsSun Cottage- "A view with a room(s)."
Cottage in Rhinebeck
4.95 out of 5 average rating, 236 reviewsRidgetop 2 Br Cabin- Views, 130acre forest & falls
Cottage in Hudson
4.88 out of 5 average rating, 154 reviewsHistoric Hudson Cottage
Private cottage rentals
Cottage in Chichester
4.99 out of 5 average rating, 517 reviewsGarden Cottage In The Catskills
Cottage in Saugerties
4.98 out of 5 average rating, 182 reviewsBlue Mountain Cottage
Cottage in Hillsdale
4.83 out of 5 average rating, 235 reviewsBig Bliss Near Catamount Cottage w/Modern Flair
Cottage in Saugerties
4.93 out of 5 average rating, 221 reviewsNew:Cozy Barn-Style Retreat Minutes From Woodstock
Cottage in Saugerties
5.0 out of 5 average rating, 317 reviewsCarriage House on Falls, Walk to Village
Cottage in Ashfield
4.97 out of 5 average rating, 302 reviewshope house
Cottage in Woodstock
4.99 out of 5 average rating, 280 reviewsGrapevine Cottage
Cottage in Rhinebeck
4.99 out of 5 average rating, 123 reviewsFabulous Lemon Cottage in Rhinebeck, NY
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