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Guesthouse holiday rentals in Berkshire County
Find and book unique guesthouse rentals on Airbnb
Top-rated Guesthouses in Berkshire County
Guests agree: These guesthouses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Berkshire County guesthouses
Family-Friendly guesthouses
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Guesthouse in Stockbridge
4.74 out of 5 average rating, 84 reviewsGuest House in Stockbridge 3 miles to Tanglewood
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Guesthouse in New Marlborough
4.91 out of 5 average rating, 185 reviewsCOZY GUESTHOUSE MINUTES AWAY FROM HIKING!
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Guesthouse in Canaan
4.92 out of 5 average rating, 172 reviewsAiry cottage with meadow views in The Berkshires
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Guesthouse in Williamstown
4.93 out of 5 average rating, 227 reviewsPerfect Base for Your Berkshire Adventure
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Guesthouse in Clarksburg
4.9 out of 5 average rating, 254 reviewsMountain Cottage Spectacular Views
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Guesthouse in Becket
4.93 out of 5 average rating, 263 reviewsCountry Cabin
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Guesthouse in Stephentown
5 out of 5 average rating, 376 reviewsDog Friendly Studio
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Guesthouse in Lenox
4.93 out of 5 average rating, 94 reviewsThe East Street Cabin
Guesthouses with a patio
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Guesthouse in Great Barrington
4.95 out of 5 average rating, 73 reviewsSweet Victorian in Housatonic
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Guesthouse in North Adams
5 out of 5 average rating, 27 reviewsBrookside Retreat
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Guesthouse in Great Barrington
4.84 out of 5 average rating, 49 reviews1-bed unit 3/4 mi. from GB dwntwn.
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Guesthouse in Williamstown
5 out of 5 average rating, 22 reviewsRitz-Carlton Bed + Espresso Bar + Sauna + Patio
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Guesthouse in Lenox
5 out of 5 average rating, 18 reviewsGuest House at Stonover Estate
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Guesthouse in Austerlitz
The Recording Studio @ Moonbeams
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Guesthouse in Stockbridge
4.8 out of 5 average rating, 10 reviewsLight-filled Carpenter's Cottage in Stockbridge
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Guesthouse in Stockbridge
5 out of 5 average rating, 3 reviewsCharming Berkshire Cottage
Guest house rentals with a washing machine and dryer
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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 Lenox
5 out of 5 average rating, 13 reviewsBella Rena Guesthouse
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Guesthouse in Lee
4.91 out of 5 average rating, 57 reviewsThe Justice's Birthplace - Modern Rustic Chic
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Guesthouse in Lee
5 out of 5 average rating, 3 reviewsThe 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, 69 reviewsZen Skylit Retreat - 12min to Tanglewood
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