Cottage holiday 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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for cottage rentals in The Berkshires
Cottage rentals with a hot tub
Cottage in Great Barrington
4.93 out of 5 average rating, 239 reviewsArtist Cottage
Cottage in Woodstock
4.9 out of 5 average rating, 377 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, 808 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, 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
Pet-friendly cottage rentals
Cottage in Kerhonkson
4.91 out of 5 average rating, 386 reviewsHome Alone Woods
Cottage in Claverack
4.98 out of 5 average rating, 247 reviews‘Clavashack’ Country Cottage
Cottage in Catskill
4.96 out of 5 average rating, 233 reviews1930's Cottage charm air conditioned near hiking
Cottage in Williamstown
4.9 out of 5 average rating, 166 reviewsCute Cozy Comfy Cottage in the Berkshires
Cottage in Argyle
4.99 out of 5 average rating, 115 reviewsThree Pines Lake House on Cossayuna Lake
Cottage in High Falls
4.99 out of 5 average rating, 415 reviewsSun Cottage- "A view with a room(s)."
Cottage in Saugerties
4.93 out of 5 average rating, 222 reviewsChic & Cozy Cottage 10 mins to Woodstock
Cottage in Rhinebeck
4.95 out of 5 average rating, 234 reviewsRidgetop 2 Br Cabin- Views, 130acre forest & falls
Private cottage rentals
Cottage in Goshen
4.98 out of 5 average rating, 106 reviewsCountry Cottage in Goshen
Cottage in Accord
4.88 out of 5 average rating, 218 reviewsSweet Cottage on a Farm Road
Cottage in Saugerties
4.93 out of 5 average rating, 221 reviewsNew:Cozy Barn-Style Retreat Minutes From Woodstock
Cottage in Hillsdale
4.83 out of 5 average rating, 235 reviewsBig Bliss Near Catamount Cottage w/Modern Flair
Cottage in Woodstock
4.99 out of 5 average rating, 279 reviewsGrapevine Cottage
Cottage in Saugerties
5.0 out of 5 average rating, 317 reviewsCarriage House on Falls, Walk to Village
Cottage in Rhinebeck
4.99 out of 5 average rating, 123 reviewsFabulous Lemon Cottage in Rhinebeck, NY
Cottage in Ashfield
4.97 out of 5 average rating, 302 reviewshope house
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