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 Brattleboro
5.0 out of 5 average rating, 200 reviewsLight Filled Loft in the Vermont Countryside
Guesthouse in Granville
4.9 out of 5 average rating, 791 reviewsMoon Valley Country Retreat no clean fee pets yes
Guesthouse in Canaan
4.93 out of 5 average rating, 166 reviewsAiry cottage with meadow views in The Berkshires
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 Schuylerville
4.97 out of 5 average rating, 385 reviewsGuesthouse in the Country near Saratoga Springs
Guesthouse in Charlestown
4.89 out of 5 average rating, 270 reviewsCozy All Season Cabin Near Beach at Rockbriar Farm
Guesthouse in Tivoli
4.94 out of 5 average rating, 213 reviewsLight-filled guest cottage
Guest house rentals with a patio
Guesthouse in Mahopac
4.93 out of 5 average rating, 116 reviewsSunny Lakeview Guesthouse
Guesthouse in Gardiner
4.99 out of 5 average rating, 139 reviewsRed Barn Retreat - Shawangunk Mountains Getaway
Guesthouse in Derry
4.96 out of 5 average rating, 114 reviewsThe Carriage House, A Modern Farmhouse
Guesthouse in Montgomery
4.93 out of 5 average rating, 123 reviewsLuxury mins from angry orchard and city winery
Guesthouse in Brewster
4.94 out of 5 average rating, 102 reviewsSherwood Barn - close to ski mountain
Guesthouse in Saratoga Springs
4.98 out of 5 average rating, 125 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 Chesterfield
4.98 out of 5 average rating, 46 reviewsHouse on a hill
Guest house rentals with a washer and dryer
Guesthouse in North Adams
5.0 out of 5 average rating, 211 reviewsNetherwood - North Adams Guest House with Views
Guesthouse in Cranston
4.92 out of 5 average rating, 305 reviewsWaterfront Studio, 10 min to Downtown Providence
Guesthouse in Marlboro
4.99 out of 5 average rating, 142 reviewsRefined, serene and like no other, Marlboro, VT.
Guesthouse in Wallingford
4.98 out of 5 average rating, 595 reviewsVermont Home Central to Ski Areas-No Cleaning Fees
Guesthouse in Glastonbury
4.96 out of 5 average rating, 133 reviewsUnique luxurious private building in historic area
Guesthouse in Belmont
4.99 out of 5 average rating, 201 reviewsCharming Pool/Garden Guest House
Guesthouse in Stonington
4.97 out of 5 average rating, 224 reviewsTrue Artist Loft, 5 minutes to downtown Mystic
Guesthouse in Mystic
4.99 out of 5 average rating, 548 reviewsGorgeous Waterfront Getaway
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