
Vacation rentals in The Berkshires
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Top-rated vacation rentals in The Berkshires
Guests agree: these stays 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 vacation rentals
Pet-friendly vacation rentals in The Berkshires

Carriage house with Chef's Kitchen, close to town

Peaceful Cabin in the Woods

Creek Side Cabin w/ Wood Fired Hot Tub & Fire Pit

Modern Upstate Cabin, near Rhinebeck NY

Stunning 2-Bedoom A-Frame in the Woods with Sauna

Modern Copake Falls Getaway - 8 Mins to Catamount

Riverfront, Fireplace & Fire Pit -20 min to Hudson

Granite Ledge, Modern home in a unique setting
House rentals in The Berkshires

Everything on one floor 2 Bdrm/1.5 Bth & Pets Ok

Spectacular Lake Views from Every Room & Garden

Belle Meade

Creekside cottage on 65 acres of land

Private Cottage/Mountain Views/Trails/Fire pit

Modern House with Mountain View @Getawind

Modern Prefabricated Architectural Retreat

Jaw dropping mountain & lake views
Pet-friendly house rentals The Berkshires

Honeybug Snug near Omega Institute!

Modern Home in Woods w/ Hot Tub 10 Miles to Hudson

The Barn - Rustic Chic Loft, Hotchkiss, Lakes, Ski

Lakefront +pets +skiing +bbq +firepit +games

Romantic Getaway at The Lake!

The Waterfall House

Private Waterfall Retreat on 10 acres

Brooksong, the perfect Berkshires getaway
Destinations to explore
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- Family travel hub Tips and inspiration
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