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Guest house holiday rentals in Berkshire County
Find and book unique guest house rentals on Airbnb
Top-rated guest house rentals in Berkshire County
Guests agree: these guest house rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for guest house rentals in Berkshire County
Family-friendly guest house rentals
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Guest house in Stockbridge
4.74 out of 5 average rating, 84 reviewsGuest House in Stockbridge 3 miles to Tanglewood
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Guest house in New Marlborough
4.91 out of 5 average rating, 185 reviewsCOZY GUESTHOUSE MINUTES AWAY FROM HIKING!
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Guest house in Canaan
4.92 out of 5 average rating, 172 reviewsAiry cottage with meadow views in The Berkshires
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Guest house in Williamstown
4.93 out of 5 average rating, 227 reviewsPerfect Base for Your Berkshire Adventure
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Guest house in Clarksburg
4.9 out of 5 average rating, 254 reviewsMountain Cottage Spectacular Views
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Guest house in Becket
4.93 out of 5 average rating, 263 reviewsCountry Cabin
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Guest house in Stephentown
5 out of 5 average rating, 376 reviewsDog Friendly Studio
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Guest house in Lenox
4.93 out of 5 average rating, 94 reviewsThe East Street Cabin
Guest house rentals with a patio
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Guest house in Great Barrington
4.95 out of 5 average rating, 73 reviewsSweet Victorian in Housatonic
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Guest house in North Adams
5 out of 5 average rating, 27 reviewsBrookside Retreat
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Guest house in Great Barrington
4.84 out of 5 average rating, 49 reviews1-bed unit 3/4 mi. from GB dwntwn.
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Guest house in Williamstown
5 out of 5 average rating, 22 reviewsRitz-Carlton Bed + Espresso Bar + Sauna + Patio
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Guest house in Lenox
5 out of 5 average rating, 18 reviewsGuest House at Stonover Estate
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Guest house in Austerlitz
The Recording Studio @ Moonbeams
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Guest house in Stockbridge
4.8 out of 5 average rating, 10 reviewsLight-filled Carpenter's Cottage in Stockbridge
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Guest house 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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Guest house in Adams
4.68 out of 5 average rating, 47 reviewsConvenience & style in downtown Adams
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Guest house in Lenox
5 out of 5 average rating, 13 reviewsBella Rena Guesthouse
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Guest house in Lee
4.91 out of 5 average rating, 57 reviewsThe Justice's Birthplace - Modern Rustic Chic
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Guest house in Lee
5 out of 5 average rating, 3 reviewsThe Blue Jay Cottage
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Guest house in Great Barrington
224 Lodge -Skiing/Entertainment
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Guest house in Lee
4.85 out of 5 average rating, 33 reviews1815 Modern Farmhouse - 10min to Tanglewood
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Guest house in Lee
4.94 out of 5 average rating, 69 reviewsZen Skylit Retreat - 12min to Tanglewood
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