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 Stockbridge
4.73 out of 5 average rating, 82 reviewsGuest House in Stockbridge 3 miles to Tanglewood
Guesthouse in Lenox
4.92 out of 5 average rating, 88 reviewsThe East Street Cabin
Guesthouse in Clarksburg
4.9 out of 5 average rating, 240 reviewsMountain Cottage Spectacular Views
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
Guesthouse in New Marlborough
4.91 out of 5 average rating, 179 reviewsCOZY GUESTHOUSE MINUTES AWAY FROM HIKING!
Guesthouse in Canaan
4.93 out of 5 average rating, 166 reviewsAiry cottage with meadow views in The Berkshires
Guesthouse in Becket
4.93 out of 5 average rating, 258 reviewsCountry Cabin
Guesthouse in Stephentown
5.0 out of 5 average rating, 360 reviewsDog Friendly Studio
Guest house rentals with a patio
Guesthouse in Great Barrington
4.96 out of 5 average rating, 49 reviewsSweet Victorian in Housatonic
Guesthouse in Lenox
5.0 out of 5 average rating, 11 reviewsGuest House at Stonover Estate
Guesthouse in Great Barrington
4.82 out of 5 average rating, 44 reviews1-bed unit 3/4 mi. from GB dwntwn. EV friendly.
Guesthouse in North Adams
5.0 out of 5 average rating, 18 reviewsBrookside Retreat
Guesthouse in Austerlitz
The Recording Studio @ Moonbeams
Guesthouse in Williamstown
5.0 out of 5 average rating, 5 reviewsSteam Room * Ritz-Carlton Bed * Walk to Williams
Guesthouse in Stockbridge
4.83 out of 5 average rating, 6 reviewsLight-filled Carpenter's Cottage in Stockbridge
Guesthouse in Stockbridge
5.0 out of 5 average rating, 3 reviewsCharming Berkshire Cottage
Guest house rentals with a washer and dryer
Guesthouse in Stockbridge
4.92 out of 5 average rating, 87 reviewsModern barn in the heart of the Berkshires
Guesthouse in Lenox
5.0 out of 5 average rating, 9 reviewsBella Rena Guesthouse
Guesthouse in Lee
4.91 out of 5 average rating, 53 reviewsThe Justice's Birthplace - 1815 Berkshires House
Guesthouse in Adams
4.68 out of 5 average rating, 47 reviewsConvenience & style in downtown Adams
Guesthouse in Great Barrington
224 Lodge -Skiing/Entertainment
Guesthouse in Lee
4.94 out of 5 average rating, 67 reviewsZen Skylit Retreat, Expansive Porch
Guesthouse in Lee
4.85 out of 5 average rating, 33 reviews1815 Farmhouse: Near Stockbridge, Lenox, Outlets
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