Guesthouse vacation rentals in Western Massachusetts
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Top-rated guesthouse rentals in Western Massachusetts
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 Western Massachusetts guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Clarksburg
4.9 out of 5 average rating, 240 reviewsMountain Cottage Spectacular Views
Guesthouse in Canaan
4.93 out of 5 average rating, 166 reviewsAiry cottage with meadow views in The Berkshires
Guesthouse in Brattleboro
5.0 out of 5 average rating, 200 reviewsLight Filled Loft in the Vermont Countryside
Guesthouse in Shrewsbury
4.72 out of 5 average rating, 198 reviewsA Comfy Hilltop Home
Guesthouse in Putney
4.95 out of 5 average rating, 322 reviewsA Vermont Carriage House
Guesthouse in Springfield
4.86 out of 5 average rating, 322 reviewsConnecticut River-Cozy Cottage
Guesthouse in Tivoli
4.94 out of 5 average rating, 211 reviewsLight-filled guest cottage
Guesthouse in Woodstock
4.96 out of 5 average rating, 185 reviewsTop of the Hill
Guest house rentals with a patio
Guesthouse in Gardiner
4.99 out of 5 average rating, 137 reviewsRed Barn Retreat - Shawangunk Mountains Getaway
Guesthouse in Brewster
4.94 out of 5 average rating, 100 reviewsSherwood Barn - close to ski mountain
Guesthouse in Montgomery
4.93 out of 5 average rating, 122 reviewsLuxury mins from angry orchard and city winery
Guesthouse in Saratoga Springs
4.98 out of 5 average rating, 122 reviewsWake up at the Track on Historic Union Ave!!!
Guesthouse in Sharon
5.0 out of 5 average rating, 66 reviewsCottage with a Waterfall View
Guesthouse in North Adams
5.0 out of 5 average rating, 19 reviewsBrookside Retreat
Guesthouse in Kerhonkson
4.95 out of 5 average rating, 56 reviewsCozy Catskills Cottage
Guesthouse in Chesterfield
4.98 out of 5 average rating, 45 reviewsHouse on a hill
Guest house rentals with a washer and dryer
Guesthouse in Marlboro
4.99 out of 5 average rating, 141 reviewsRefined, serene and like no other, Marlboro, VT.
Guesthouse in Cranston
4.92 out of 5 average rating, 303 reviewsWaterfront Studio, 10 min to Downtown Providence
Guesthouse in Glastonbury
4.96 out of 5 average rating, 133 reviewsUnique luxurious private building in historic area
Guesthouse in Beacon
4.94 out of 5 average rating, 367 reviewsCozy Mountainside Suite - Minutes from Beacon
Guesthouse in New Paltz
4.99 out of 5 average rating, 390 reviewsRidge View Walk-Up | Your GUNKS Home
Guesthouse in Woodstock
5.0 out of 5 average rating, 301 reviewsSteps toTown/Bus Pet Ok/No Extra Fees! &Five Star
Guesthouse in Stanfordville
4.92 out of 5 average rating, 164 reviewsEco Cottage in the Woods
Guesthouse in Worcester
4.81 out of 5 average rating, 210 reviewsCarriage house apartment
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