Guesthouse vacation rentals in Berkshire County
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Top-rated guesthouse rentals in Berkshire County
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Berkshire County guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Stephentown
5 out of 5 average rating, 387 reviewsDog Friendly Studio
Guesthouse in Lenox
4.93 out of 5 average rating, 102 reviewsThe East Street Cabin
Guesthouse in New Marlborough
4.91 out of 5 average rating, 192 reviewsCOZY GUESTHOUSE MINUTES AWAY FROM HIKING!
Guesthouse in Clarksburg
4.91 out of 5 average rating, 264 reviewsMountain Cottage Spectacular Views
Guesthouse in Stockbridge
4.71 out of 5 average rating, 91 reviewsGuest House in Stockbridge 3 miles to Tanglewood
Guesthouse in Williamstown
4.93 out of 5 average rating, 232 reviewsPerfect Base for Your Berkshire Adventure
Guesthouse in Becket
4.93 out of 5 average rating, 267 reviewsCountry Cabin
Guesthouse in Canaan
4.93 out of 5 average rating, 176 reviewsAiry cottage with meadow views in The Berkshires
Guest house rentals with a patio
Guesthouse in Pittsfield
4.96 out of 5 average rating, 72 reviewsThe Nest at Birdland
Guesthouse in Stockbridge
4.83 out of 5 average rating, 12 reviewsLight-filled Carpenter's Cottage in Stockbridge
Guesthouse in Great Barrington
5 out of 5 average rating, 4 reviewsBerkshires Guest Barn
Guesthouse in Alford
Alford beauty
Guesthouse in Austerlitz
The Recording Studio @ Moonbeams
Guesthouse in North Adams
4.94 out of 5 average rating, 32 reviewsBrookside Retreat
Guesthouse in Great Barrington
4.94 out of 5 average rating, 90 reviewsSweet Victorian in Housatonic
Guesthouse in Great Barrington
4.85 out of 5 average rating, 54 reviews1-bed unit 3/4 mi. from GB dwntwn.
Guest house rentals with a washer and dryer
Guesthouse in Adams
4.69 out of 5 average rating, 48 reviewsConvenience & style in downtown Adams
Guesthouse in Lee
4.9 out of 5 average rating, 10 reviewsThe Blue Jay Cottage
Guesthouse in Lenox
5 out of 5 average rating, 19 reviewsBella Rena Guesthouse
Guesthouse in Lee
4.92 out of 5 average rating, 62 reviewsThe Justice's Birthplace - Modern Rustic Chic
Guesthouse in Lee
4.85 out of 5 average rating, 34 reviews1815 Modern Farmhouse - 10min to Tanglewood
Guesthouse in Lee
4.94 out of 5 average rating, 72 reviewsZen Skylit Retreat - 12min to Tanglewood
Guesthouse in Great Barrington
224 Lodge -Skiing/Entertainment
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