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Guesthouse vacation rentals in Berkshire County
Find and book unique guesthouse rentals on Airbnb
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
Get the amount of space that is right for you
Popular amenities for Berkshire County guesthouse rentals
Family-friendly guest house rentals
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Guesthouse in Stockbridge
4.73 out of 5 average rating, 82 reviewsGuest House in Stockbridge 3 miles to Tanglewood
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Guesthouse in Canaan
4.93 out of 5 average rating, 167 reviewsAiry cottage with meadow views in The Berkshires
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Guesthouse in Clarksburg
4.9 out of 5 average rating, 246 reviewsMountain Cottage Spectacular Views
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Guesthouse in New Marlborough
4.91 out of 5 average rating, 183 reviewsCOZY GUESTHOUSE MINUTES AWAY FROM HIKING!
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Guesthouse in Becket
4.93 out of 5 average rating, 260 reviewsCountry Cabin
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Guesthouse in Williamstown
4.93 out of 5 average rating, 221 reviewsPerfect Base for Your Berkshire Adventure
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Guesthouse in Stephentown
5 out of 5 average rating, 371 reviewsDog Friendly Studio
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Guesthouse in Lenox
4.92 out of 5 average rating, 89 reviewsThe East Street Cabin
Guest house rentals with a patio
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Guesthouse in North Adams
5 out of 5 average rating, 24 reviewsBrookside Retreat
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Guesthouse in Lenox
5 out of 5 average rating, 13 reviewsGuest House at Stonover Estate
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Guesthouse in Great Barrington
4.82 out of 5 average rating, 45 reviews1-bed unit 3/4 mi. from GB dwntwn. EV friendly.
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Guesthouse in Austerlitz
The Recording Studio @ Moonbeams
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Guesthouse in Williamstown
5 out of 5 average rating, 13 reviewsRitz-Carlton Bed * Patio * Shower & Steam Room
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Guesthouse in Stockbridge
4.78 out of 5 average rating, 9 reviewsLight-filled Carpenter's Cottage in Stockbridge
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Guesthouse in Stockbridge
5 out of 5 average rating, 3 reviewsCharming Berkshire Cottage
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Guesthouse in Sheffield
5 out of 5 average rating, 3 reviewsThe Cottage at 3 Sisters Farm
Guest house rentals with a washer and dryer
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Guesthouse in Lenox
5 out of 5 average rating, 10 reviewsBella Rena Guesthouse
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Guesthouse in Stockbridge
4.92 out of 5 average rating, 95 reviewsModern barn in the heart of the Berkshires
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Guesthouse in Lee
4.91 out of 5 average rating, 54 reviewsThe Justice's Birthplace - Modern Rustic Chic
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Guesthouse in Adams
4.68 out of 5 average rating, 47 reviewsConvenience & style in downtown Adams
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Guesthouse in Lee
New place to stayThe Blue Jay Cottage
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Guesthouse in Great Barrington
224 Lodge -Skiing/Entertainment
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Guesthouse in Lee
4.85 out of 5 average rating, 33 reviews1815 Modern Farmhouse - 10min to Tanglewood
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Guesthouse in Lee
4.94 out of 5 average rating, 67 reviewsZen Skylit Retreat - 12min to Tanglewood
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