Guesthouse accommodation & holiday 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.
Holiday rentals for every style
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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
10 – 17 Jan
Guesthouse in Lenox
4.92 out of 5 average rating, 88 reviewsThe East Street Cabin
4 – 11 Sept
Guesthouse in Clarksburg
4.9 out of 5 average rating, 240 reviewsMountain Cottage Spectacular Views
15 – 22 Mar
Guesthouse in New Marlborough
4.91 out of 5 average rating, 180 reviewsCOZY GUESTHOUSE MINUTES AWAY FROM HIKING!
29 Mar – 5 Apr
Guesthouse in Canaan
4.93 out of 5 average rating, 166 reviewsAiry cottage with meadow views in The Berkshires
2 – 9 Mar
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
16 – 23 June
Guesthouse in Becket
4.93 out of 5 average rating, 258 reviewsCountry Cabin
9 – 16 Oct
Guesthouse in Stephentown
5.0 out of 5 average rating, 361 reviewsDog Friendly Studio
25 Jan – 1 Feb
Guesthouses with a patio
Guesthouse in North Adams
5.0 out of 5 average rating, 18 reviewsBrookside Retreat
17 – 24 May
Guesthouse in Great Barrington
4.82 out of 5 average rating, 44 reviews1-bed unit 3/4 mi. from GB dwntwn. EV friendly.
13 – 20 June
Guesthouse in Lenox
5.0 out of 5 average rating, 11 reviewsGuest House at Stonover Estate
8 – 15 Nov
Guesthouse in Austerlitz
The Recording Studio @ Moonbeams
29 Sept – 6 Oct
Guesthouse in Stockbridge
4.86 out of 5 average rating, 7 reviewsLight-filled Carpenter's Cottage in Stockbridge
11 – 18 Sept
Guesthouse in Williamstown
5.0 out of 5 average rating, 6 reviewsSteam Sauna * Ritz-Carlton Bed * Walk to Williams
31 July – 7 Aug
Guesthouse in Stockbridge
5.0 out of 5 average rating, 3 reviewsCharming Berkshire Cottage
14 – 21 Apr
Guesthouse in Sheffield
5.0 out of 5 average rating, 3 reviewsThe Cottage at 3 Sisters Farm
3 – 10 Oct
Guest house rentals with a washing machine and dryer
Guesthouse in Stockbridge
4.92 out of 5 average rating, 89 reviewsModern barn in the heart of the Berkshires
29 Sept – 6 Oct
Guesthouse in Lenox
5.0 out of 5 average rating, 9 reviewsBella Rena Guesthouse
16 – 23 Dec
Guesthouse in Lee
4.91 out of 5 average rating, 53 reviewsThe Justice's Birthplace - 1815 Berkshires House
3 – 10 June
Guesthouse in Adams
4.68 out of 5 average rating, 47 reviewsConvenience & style in downtown Adams
28 Aug – 4 Sept
Guesthouse in Great Barrington
224 Lodge -Skiing/Entertainment
10 – 17 Oct
Guesthouse in Lee
4.85 out of 5 average rating, 33 reviews1815 Farmhouse: Near Stockbridge, Lenox, Outlets
16 – 23 Feb
Guesthouse in Lee
4.94 out of 5 average rating, 67 reviewsZen Skylit Retreat, Expansive Porch
24 Nov – 1 Dec
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