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.
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Vacation rentals for every style
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Popular amenities for Berkshire County guesthouse rentals
Family-friendly guest house rentals
Guest favorite
Guesthouse in Stephentown
5 out of 5 average rating, 394 reviewsDog Friendly Studio
Guest favorite
Guesthouse in New Marlborough
4.9 out of 5 average rating, 196 reviewsCOZY GUESTHOUSE MINUTES AWAY FROM HIKING!
Guesthouse in Stockbridge
4.71 out of 5 average rating, 91 reviewsGuest House in Stockbridge 3 miles to Tanglewood
Guest favorite
Guesthouse in Williamstown
4.93 out of 5 average rating, 238 reviewsPerfect Base for Your Berkshire Adventure
Guest favorite
Guesthouse in Becket
4.93 out of 5 average rating, 269 reviewsCountry Cabin
Guest favorite
Guesthouse in Canaan
4.93 out of 5 average rating, 182 reviewsAiry cottage with meadow views in The Berkshires
Guest house rentals with a patio
Guest favorite
Guesthouse in Pittsfield
4.95 out of 5 average rating, 78 reviewsThe Nest at Birdland
Guest favorite
Guesthouse in Great Barrington
5 out of 5 average rating, 6 reviewsBerkshires Guest Barn
Superhost
Guesthouse in Great Barrington
4.84 out of 5 average rating, 57 reviews1-bed unit 3/4 mi. from GB dwntwn.
Guest house rentals with a washer and dryer
Superhost
Guesthouse in Adams
4.69 out of 5 average rating, 48 reviewsConvenience & style in downtown Adams
Superhost
Guesthouse in Lee
4.92 out of 5 average rating, 13 reviewsThe Blue Jay Cottage
Guest favorite
Guesthouse in Lenox
5 out of 5 average rating, 24 reviewsBella Rena Guesthouse
Guest favorite
Guesthouse in Lee
4.9 out of 5 average rating, 67 reviewsJustice's Birthplace - 1815 Rustic Chic + Modern
Guest favorite
Guesthouse in Lee
4.86 out of 5 average rating, 35 reviews1815 Modern Farmhouse - 15min to Fairview BHS
Guest favorite
Guesthouse in Lee
4.95 out of 5 average rating, 73 reviewsZen Skylit Retreat - near Austen Riggs, Tanglewood
Guest favorite
Guesthouse in Becket
4.96 out of 5 average rating, 54 reviewsGuest House Sanctuary by Evergreen Home
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