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.
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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
May 20 – 27
Guesthouse in Lenox
4.92 out of 5 average rating, 88 reviewsThe East Street Cabin
Jul 26 – Aug 2
Guesthouse in Clarksburg
4.9 out of 5 average rating, 240 reviewsMountain Cottage Spectacular Views
Jul 12 – 19
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
Sep 8 – 15
Guesthouse in New Marlborough
4.91 out of 5 average rating, 179 reviewsCOZY GUESTHOUSE MINUTES AWAY FROM HIKING!
Jul 29 – Aug 5
Guesthouse in Canaan
4.93 out of 5 average rating, 166 reviewsAiry cottage with meadow views in The Berkshires
Dec 3 – 10
Guesthouse in Becket
4.93 out of 5 average rating, 258 reviewsCountry Cabin
Dec 21 – 28
Guesthouse in Stephentown
5.0 out of 5 average rating, 360 reviewsDog Friendly Studio
Feb 17 – 24
Guest house rentals with a patio
Guesthouse in Great Barrington
4.96 out of 5 average rating, 49 reviewsSweet Victorian in Housatonic
Jun 9 – 16
Guesthouse in Lenox
5.0 out of 5 average rating, 11 reviewsGuest House at Stonover Estate
Nov 6 – 13
Guesthouse in Great Barrington
4.82 out of 5 average rating, 44 reviews1-bed unit 3/4 mi. from GB dwntwn. EV friendly.
Jun 14 – 21
Guesthouse in North Adams
5.0 out of 5 average rating, 18 reviewsBrookside Retreat
Jun 18 – 25
Guesthouse in Austerlitz
The Recording Studio @ Moonbeams
Sep 23 – 30
Guesthouse in Williamstown
5.0 out of 5 average rating, 5 reviewsSteam Room * Ritz-Carlton Bed * Walk to Williams
Sep 25 – Oct 2
Guesthouse in Stockbridge
4.83 out of 5 average rating, 6 reviewsLight-filled Carpenter's Cottage in Stockbridge
Jun 9 – 16
Guesthouse in Stockbridge
5.0 out of 5 average rating, 3 reviewsCharming Berkshire Cottage
Jun 15 – 22
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
Oct 14 – 21
Guesthouse in Lenox
5.0 out of 5 average rating, 9 reviewsBella Rena Guesthouse
May 12 – 19
Guesthouse in Lee
4.91 out of 5 average rating, 53 reviewsThe Justice's Birthplace - 1815 Berkshires House
May 28 – Jun 4
Guesthouse in Adams
4.68 out of 5 average rating, 47 reviewsConvenience & style in downtown Adams
Aug 16 – 23
Guesthouse in Great Barrington
224 Lodge -Skiing/Entertainment
Dec 12 – 19
Guesthouse in Lee
4.94 out of 5 average rating, 67 reviewsZen Skylit Retreat, Expansive Porch
Dec 12 – 19
Guesthouse in Lee
4.85 out of 5 average rating, 33 reviews1815 Farmhouse: Near Stockbridge, Lenox, Outlets
Aug 22 – 29
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