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
Get the amount of space that is right for you
Popular amenities for guest house rentals in Berkshire County
Family-friendly guest house rentals
Guest house in Stephentown
5 out of 5 average rating, 388 reviewsDog Friendly Studio
Guest house in New Marlborough
4.9 out of 5 average rating, 195 reviewsCOZY GUESTHOUSE MINUTES AWAY FROM HIKING!
Guest house in Stockbridge
4.71 out of 5 average rating, 91 reviewsGuest House in Stockbridge 3 miles to Tanglewood
Guest house in Williamstown
4.93 out of 5 average rating, 236 reviewsPerfect Base for Your Berkshire Adventure
Guest house in Becket
4.93 out of 5 average rating, 268 reviewsCountry Cabin
Guest house in Canaan
4.93 out of 5 average rating, 180 reviewsAiry cottage with meadow views in The Berkshires
Guest house rentals with a patio
Guest house in Pittsfield
4.95 out of 5 average rating, 77 reviewsThe Nest at Birdland
Guest house in Great Barrington
5 out of 5 average rating, 6 reviewsBerkshires Guest Barn
Guest house in Alford
Alford beauty
Guest house in Austerlitz
The Recording Studio @ Moonbeams
Private room in New Lebanon
Cascades Queen A
Guest house in Great Barrington
4.84 out of 5 average rating, 57 reviews1-bed unit 3/4 mi. from GB dwntwn.
Private room in New Lebanon
Cascades Premium King B
Private room in New Lebanon
Cascades Premium King A
Guest house rentals with a washing machine and dryer
Guest house in Adams
4.69 out of 5 average rating, 48 reviewsConvenience & style in downtown Adams
Guest house in Lee
4.92 out of 5 average rating, 13 reviewsThe Blue Jay Cottage
Guest house in Lenox
5 out of 5 average rating, 24 reviewsBella Rena Guesthouse
Guest house in Lee
4.89 out of 5 average rating, 65 reviewsThe Justice's Birthplace - Modern Rustic Chic
Guest house in Lee
4.85 out of 5 average rating, 34 reviews1815 Modern Farmhouse - 10min to Tanglewood
Guest house in Lee
4.95 out of 5 average rating, 73 reviewsZen Skylit Retreat - 12min to Tanglewood
Guest house in Great Barrington
224 Lodge -Skiing/Entertainment
Guest house in Lanesborough
5 out of 5 average rating, 7 reviewsThe Carriage House: Spotless, Charming 2 Bedroom
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