Guesthouse vacation rentals in The Berkshires
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Top-rated guesthouse rentals in The Berkshires
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for The Berkshires guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Clarksburg
4.9 out of 5 average rating, 240 reviewsMountain Cottage Spectacular Views
Jul 28 – Aug 4
Guesthouse in Tivoli
4.94 out of 5 average rating, 211 reviewsLight-filled guest cottage
Jul 18 – 25
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
Oct 14 – 21
Guesthouse in Northampton
4.92 out of 5 average rating, 240 reviewsLarge Studio – Walk to Town
Jan 13 – 20
Guesthouse in Woodstock
4.96 out of 5 average rating, 185 reviewsTop of the Hill
Sep 26 – Oct 3
Guesthouse in Ulster Park
4.85 out of 5 average rating, 458 reviewsHudson Valley Hideaway
Nov 22 – 29
Guesthouse in Woodstock
4.86 out of 5 average rating, 831 reviewsRocket Room - Rock Stars Only
Jan 20 – 27
Guesthouse in Belchertown
4.94 out of 5 average rating, 134 reviewsAmherst Area Studio Apartment
Oct 4 – 11
Guest house rentals with a patio
Guesthouse in Mahopac
4.96 out of 5 average rating, 113 reviewsSunny Lakeview Guesthouse
Oct 30 – Nov 6
Guesthouse in Gardiner
4.99 out of 5 average rating, 137 reviewsRed Barn Retreat - Shawangunk Mountains Getaway
Jun 12 – 19
Guesthouse in Montgomery
4.93 out of 5 average rating, 122 reviewsLuxury mins from angry orchard and city winery
Dec 3 – 10
Guesthouse in Saratoga Springs
4.98 out of 5 average rating, 121 reviewsWake up at the Track on Historic Union Ave!!!
Feb 5 – 12
Guesthouse in Sharon
5.0 out of 5 average rating, 65 reviewsCottage with a Waterfall View
Sep 25 – Oct 2
Guesthouse in Pittsfield
4.98 out of 5 average rating, 47 reviewsThe Nest at Birdland
Dec 24 – 31
Guesthouse in New Milford
5.0 out of 5 average rating, 43 reviewsLuxury in the Litchfield Hills
Mar 28 – Apr 4
Guesthouse in Lenox
5.0 out of 5 average rating, 11 reviewsGuest House at Stonover Estate
May 13 – 20
Guest house rentals with a washer and dryer
Guesthouse in North Adams
5.0 out of 5 average rating, 209 reviewsNetherwood - North Adams Guest House with Views
Dec 22 – 29
Guesthouse in Glastonbury
4.96 out of 5 average rating, 133 reviewsUnique luxurious private building in historic area
Jul 21 – 28
Guesthouse in Beacon
4.94 out of 5 average rating, 367 reviewsCozy Mountainside Suite - Minutes from Beacon
Mar 2 – 9
Guesthouse in Marlboro
4.99 out of 5 average rating, 141 reviewsRefined, serene and like no other, Marlboro, VT.
Nov 27 – Dec 4
Guesthouse in Brewster
5.0 out of 5 average rating, 291 reviewsThe Cottage by the Lake: Hudson Valley Indulgence
Aug 1 – 8
Guesthouse in Northampton
4.94 out of 5 average rating, 181 reviewsLittle Blue Studio
Oct 9 – 16
Guesthouse in Stanfordville
4.92 out of 5 average rating, 164 reviewsEco Cottage in the Woods
Dec 2 – 9
Guesthouse in Woodstock
5.0 out of 5 average rating, 301 reviewsSteps toTown/Bus Pet Ok/No Extra Fees! &Five Star
Mar 28 – Apr 4
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