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