Guesthouse vacation rentals in The Berkshires
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Top-rated guesthouse rentals in The Berkshires
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.
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Popular amenities for The Berkshires guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Clarksburg
4.9 out of 5 average rating, 240 reviewsMountain Cottage Spectacular Views
Guesthouse in Canaan
4.93 out of 5 average rating, 166 reviewsAiry cottage with meadow views in The Berkshires
Guesthouse in Ulster Park
4.85 out of 5 average rating, 459 reviewsHudson Valley Hideaway
Guesthouse in Belchertown
4.94 out of 5 average rating, 137 reviewsAmherst Area Studio Apartment
Guesthouse in Woodstock
4.96 out of 5 average rating, 185 reviewsTop of the Hill
Guesthouse in Woodstock
4.86 out of 5 average rating, 834 reviewsRocket Room - Rock Stars Only
Guesthouse in Schuylerville
4.97 out of 5 average rating, 385 reviewsGuesthouse in the Country near Saratoga Springs
Guesthouse in Putney
4.95 out of 5 average rating, 322 reviewsA Vermont Carriage House
Guest house rentals with a patio
Guesthouse in Mahopac
4.93 out of 5 average rating, 116 reviewsSunny Lakeview Guesthouse
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 Brewster
4.94 out of 5 average rating, 102 reviewsSherwood Barn - close to ski mountain
Guesthouse in Saratoga Springs
4.98 out of 5 average rating, 125 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, 52 reviewsSweet Victorian in Housatonic
Guest house rentals with a washer and dryer
Guesthouse in North Adams
5.0 out of 5 average rating, 211 reviewsNetherwood - North Adams Guest House with Views
Guesthouse in Fort Plain
4.98 out of 5 average rating, 447 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 New Paltz
4.99 out of 5 average rating, 390 reviewsRidge View Walk-Up | Your GUNKS Home
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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