Guesthouse vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Berkshire County guesthouses
Family-friendly guesthouses
Guesthouse in Stockbridge
4.73 out of 5 average rating, 82 reviewsGuest House in Stockbridge 3 miles to Tanglewood
Guesthouse in Clarksburg
4.9 out of 5 average rating, 241 reviewsMountain Cottage Spectacular Views
Guesthouse in New Marlborough
4.91 out of 5 average rating, 181 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 Williamstown
4.93 out of 5 average rating, 220 reviewsPerfect Base for Your Berkshire Adventure
Guesthouse in Stephentown
5.0 out of 5 average rating, 367 reviewsDog Friendly Studio
Guesthouse in Lenox
4.92 out of 5 average rating, 89 reviewsThe East Street Cabin
Guesthouses with a patio
Guesthouse in North Adams
5.0 out of 5 average rating, 21 reviewsBrookside Retreat
Guesthouse in Austerlitz
The Recording Studio @ Moonbeams
Guesthouse in Williamstown
5.0 out of 5 average rating, 10 reviewsSteam Sauna * Ritz-Carlton Bed * Walk to Williams
Guesthouse in Stockbridge
5.0 out of 5 average rating, 3 reviewsCharming Berkshire Cottage
Guesthouse in New Lebanon
Cascades Queen A
Guesthouse in New Lebanon
Cascades Premium King A
Guesthouse in New Lebanon
Cascades Premium King B
Guesthouse in New Lebanon
Cascades Super Premium King
Guesthouse rentals with a washer and dryer
Guesthouse in Stockbridge
4.91 out of 5 average rating, 92 reviewsModern barn in the heart of the Berkshires
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 Lenox
5.0 out of 5 average rating, 12 reviewsGuest House at Stonover Estate
Guesthouse in Lenox
5.0 out of 5 average rating, 10 reviewsBella Rena Guesthouse
Guesthouse in Lee
4.91 out of 5 average rating, 53 reviewsThe Justice's Birthplace - 1815 Berkshires House
Guesthouse in Stockbridge
4.78 out of 5 average rating, 9 reviewsLight-filled Carpenter's Cottage in Stockbridge
Guesthouse in Adams
4.68 out of 5 average rating, 47 reviewsConvenience & style in downtown Adams
Guesthouse in Sheffield
5.0 out of 5 average rating, 3 reviewsThe Cottage at 3 Sisters Farm
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