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 19 – 26
Guesthouse in Tivoli
4.94 out of 5 average rating, 211 reviewsLight-filled guest cottage
Jul 25 – Aug 1
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
Aug 29 – Sep 5
Guesthouse in Northampton
4.92 out of 5 average rating, 240 reviewsLarge Studio – Walk to Town
Jan 13 – 20
Guesthouse in Springfield
4.86 out of 5 average rating, 322 reviewsConnecticut River-Cozy Cottage
Apr 5 – 12
Guesthouse in Woodstock
4.86 out of 5 average rating, 831 reviewsRocket Room - Rock Stars Only
Jan 18 – 25
Guesthouse in Brattleboro
4.99 out of 5 average rating, 199 reviewsLight Filled Loft in the Vermont Countryside
May 7 – 14
Guesthouse in Ulster Park
4.85 out of 5 average rating, 457 reviewsHudson Valley Hideaway
Jan 9 – 16
Guest house rentals with a patio
Guesthouse in Mahopac
4.96 out of 5 average rating, 113 reviewsSunny Lakeview Guesthouse
Dec 30 – Jan 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, 120 reviewsLuxury mins from angry orchard and city winery
Nov 15 – 22
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
Aug 21 – 28
Guesthouse in Pittsfield
4.98 out of 5 average rating, 47 reviewsThe Nest at Birdland
Dec 22 – 29
Guesthouse in Great Barrington
4.96 out of 5 average rating, 50 reviewsSweet Victorian in Housatonic
Jun 1 – 8
Guesthouse in New Milford
5.0 out of 5 average rating, 43 reviewsLuxury in the Litchfield Hills
Nov 26 – Dec 3
Guest house rentals with a washer and dryer
Guesthouse in North Adams
5.0 out of 5 average rating, 208 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
Sep 27 – Oct 4
Guesthouse in Beacon
4.94 out of 5 average rating, 367 reviewsCozy Mountainside Suite - Minutes from Beacon
Apr 28 – May 5
Guesthouse in New Paltz
4.99 out of 5 average rating, 387 reviewsRidge View Walk-Up | Your GUNKS Home
Jun 11 – 18
Guesthouse in Marlboro
4.99 out of 5 average rating, 141 reviewsRefined, serene and like no other, Marlboro, VT.
Jun 25 – Jul 2
Guesthouse in Brewster
5.0 out of 5 average rating, 290 reviewsThe Cottage by the Lake: Hudson Valley Indulgence
Aug 1 – 8
Guesthouse in Woodstock
5.0 out of 5 average rating, 301 reviewsSteps toTown/Bus Pet Ok/No Extra Fees! &Five Star
Dec 11 – 18
Guesthouse in Stanfordville
4.92 out of 5 average rating, 164 reviewsEco Cottage in the Woods
Feb 14 – 21
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