Guesthouse vacation rentals in The Berkshires
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Top-rated guesthouses in The Berkshires
Guests agree: these guesthouses 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 guesthouses
Family-friendly guesthouses
Guesthouse in Clarksburg
4.9 out of 5 average rating, 240 reviewsMountain Cottage Spectacular Views
Guesthouse in Ulster Park
4.85 out of 5 average rating, 459 reviewsHudson Valley Hideaway
Guesthouse in Woodstock
4.86 out of 5 average rating, 833 reviewsRocket Room - Rock Stars Only
Guesthouse in Northampton
4.93 out of 5 average rating, 241 reviewsLarge Studio – Walk to Town
Guesthouse in Woodstock
4.96 out of 5 average rating, 185 reviewsTop of the Hill
Guesthouse in Springfield
4.86 out of 5 average rating, 324 reviewsConnecticut River-Cozy Cottage
Guesthouse in Schuylerville
4.97 out of 5 average rating, 384 reviewsGuesthouse in the Country near Saratoga Springs
Guesthouse in Belchertown
4.94 out of 5 average rating, 136 reviewsAmherst Area Studio Apartment
Guesthouses with a patio
Guesthouse in Mahopac
4.93 out of 5 average rating, 116 reviewsSunny Lakeview Guesthouse
Guesthouse in Brewster
4.94 out of 5 average rating, 101 reviewsSherwood Barn - close to ski mountain
Guesthouse in Gardiner
4.99 out of 5 average rating, 139 reviewsRed Barn Retreat - Shawangunk Mountains Getaway
Guesthouse in Montgomery
4.93 out of 5 average rating, 123 reviewsLuxury mins from angry orchard and city winery
Guesthouse in Saratoga Springs
4.98 out of 5 average rating, 124 reviewsWake up at the Track on Historic Union Ave!!!
Guesthouse in Sharon
5.0 out of 5 average rating, 66 reviewsCottage with a Waterfall View
Guesthouse in Pittsfield
4.98 out of 5 average rating, 47 reviewsThe Nest at Birdland
Guesthouse in Great Barrington
4.96 out of 5 average rating, 51 reviewsSweet Victorian in Housatonic
Guesthouse rentals with a washer and dryer
Guesthouse in North Adams
5.0 out of 5 average rating, 210 reviewsNetherwood - North Adams Guest House with Views
Guesthouse in Fort Plain
4.99 out of 5 average rating, 446 reviewsStarhaven: Baseball HoF, Mineral Mining & More
Guesthouse in Glastonbury
4.96 out of 5 average rating, 133 reviewsUnique luxurious private building in historic area
Guesthouse in Brewster
5.0 out of 5 average rating, 291 reviewsThe Cottage by the Lake: Hudson Valley Indulgence
Guesthouse in Stanfordville
4.92 out of 5 average rating, 165 reviewsEco Cottage in the Woods
Guesthouse in Marlboro
4.99 out of 5 average rating, 142 reviewsRefined, serene and like no other, Marlboro, VT.
Guesthouse in Woodstock
5.0 out of 5 average rating, 302 reviewsSteps toTown/Bus Pet Ok/No Extra Fees! &Five Star
Guesthouse in Northampton
4.94 out of 5 average rating, 182 reviewsLittle Blue Studio
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