Guesthouse vacation rentals in Berkshire County
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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
Jan. 8 – 15
Guesthouse in Lenox
4.92 out of 5 average rating, 88 reviewsThe East Street Cabin
Sep. 3 – 10
Guesthouse in Clarksburg
4.9 out of 5 average rating, 240 reviewsMountain Cottage Spectacular Views
Jun. 11 – 18
Guesthouse in New Marlborough
4.91 out of 5 average rating, 180 reviewsCOZY GUESTHOUSE MINUTES AWAY FROM HIKING!
Nov. 16 – 23
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
Sep. 26 – Oct. 3
Guesthouse in Canaan
4.93 out of 5 average rating, 166 reviewsAiry cottage with meadow views in The Berkshires
Nov. 8 – 15
Guesthouse in Becket
4.93 out of 5 average rating, 258 reviewsCountry Cabin
Oct. 7 – 14
Guesthouse in Stephentown
5.0 out of 5 average rating, 361 reviewsDog Friendly Studio
Dec. 16 – 23
Guesthouses with a patio
Guesthouse in Pittsfield
4.98 out of 5 average rating, 47 reviewsThe Nest at Birdland
Jul. 23 – 30
Guesthouse in North Adams
5.0 out of 5 average rating, 18 reviewsBrookside Retreat
May 17 – 24
Guesthouse in Great Barrington
4.82 out of 5 average rating, 44 reviews1-bed unit 3/4 mi. from GB dwntwn. EV friendly.
Jun. 11 – 18
Guesthouse in Lenox
5.0 out of 5 average rating, 11 reviewsGuest House at Stonover Estate
Oct. 5 – 12
Guesthouse in Austerlitz
The Recording Studio @ Moonbeams
Sep. 27 – Oct. 4
Guesthouse in Stockbridge
4.83 out of 5 average rating, 6 reviewsLight-filled Carpenter's Cottage in Stockbridge
Nov. 12 – 19
Guesthouse in Williamstown
5.0 out of 5 average rating, 6 reviewsSteam Room * Ritz-Carlton Bed * Walk to Williams
Oct. 13 – 20
Guesthouse in Stockbridge
5.0 out of 5 average rating, 3 reviewsCharming Berkshire Cottage
Apr. 11 – 18
Guesthouse rentals with a washer and dryer
Guesthouse in Stockbridge
4.92 out of 5 average rating, 89 reviewsModern barn in the heart of the Berkshires
May 15 – 22
Guesthouse in Lenox
5.0 out of 5 average rating, 9 reviewsBella Rena Guesthouse
Sep. 28 – Oct. 5
Guesthouse in Lee
4.91 out of 5 average rating, 53 reviewsThe Justice's Birthplace - 1815 Berkshires House
Jan. 16 – 23
Guesthouse in Adams
4.68 out of 5 average rating, 47 reviewsConvenience & style in downtown Adams
Aug. 21 – 28
Guesthouse in Great Barrington
224 Lodge -Skiing/Entertainment
Jul. 22 – 29
Guesthouse in Lee
4.94 out of 5 average rating, 67 reviewsZen Skylit Retreat, Expansive Porch
Nov. 22 – 29
Guesthouse in Lee
4.85 out of 5 average rating, 33 reviews1815 Farmhouse: Near Stockbridge, Lenox, Outlets
Aug. 26 – Sep. 2
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