Guesthouse vacation rentals in Western Massachusetts
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Top-rated guesthouses in Western Massachusetts
Guests agree: these guesthouses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Western Massachusetts guesthouses
Family-friendly guesthouses
Guesthouse in Clarksburg
4.9 out of 5 average rating, 240 reviewsMountain Cottage Spectacular Views
Feb. 11 – 18
Guesthouse in Canaan
4.93 out of 5 average rating, 166 reviewsAiry cottage with meadow views in The Berkshires
May 15 – 22
Guesthouse in Brattleboro
5.0 out of 5 average rating, 200 reviewsLight Filled Loft in the Vermont Countryside
Jul. 22 – 29
Guesthouse in Shrewsbury
4.72 out of 5 average rating, 198 reviewsA Comfy Hilltop Home
Jan. 10 – 17
Guesthouse in Putney
4.95 out of 5 average rating, 322 reviewsA Vermont Carriage House
Aug. 15 – 22
Guesthouse in Springfield
4.86 out of 5 average rating, 322 reviewsConnecticut River-Cozy Cottage
Jan. 25 – Feb. 1
Guesthouse in Tivoli
4.94 out of 5 average rating, 211 reviewsLight-filled guest cottage
Jun. 14 – 21
Guesthouse in Woodstock
4.96 out of 5 average rating, 185 reviewsTop of the Hill
Nov. 12 – 19
Guesthouses with a patio
Guesthouse in Gardiner
4.99 out of 5 average rating, 137 reviewsRed Barn Retreat - Shawangunk Mountains Getaway
May 28 – Jun. 4
Guesthouse in Brewster
4.94 out of 5 average rating, 100 reviewsSherwood Barn - close to ski mountain
Sep. 3 – 10
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, 122 reviewsWake up at the Track on Historic Union Ave!!!
Nov. 13 – 20
Guesthouse in Sharon
5.0 out of 5 average rating, 66 reviewsCottage with a Waterfall View
Sep. 22 – 29
Guesthouse in North Adams
5.0 out of 5 average rating, 19 reviewsBrookside Retreat
May 17 – 24
Guesthouse in Kerhonkson
4.95 out of 5 average rating, 56 reviewsCozy Catskills Cottage
Apr. 26 – May 3
Guesthouse in Chesterfield
4.98 out of 5 average rating, 45 reviewsHouse on a hill
Aug. 28 – Sep. 4
Guesthouse 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.
Dec. 1 – 8
Guesthouse in Cranston
4.92 out of 5 average rating, 303 reviewsWaterfront Studio, 10 min to Downtown Providence
Oct. 11 – 18
Guesthouse in Glastonbury
4.96 out of 5 average rating, 133 reviewsUnique luxurious private building in historic area
Jul. 23 – 30
Guesthouse in Beacon
4.94 out of 5 average rating, 367 reviewsCozy Mountainside Suite - Minutes from Beacon
Nov. 9 – 16
Guesthouse in New Paltz
4.99 out of 5 average rating, 390 reviewsRidge View Walk-Up | Your GUNKS Home
Jun. 12 – 19
Guesthouse in Woodstock
5.0 out of 5 average rating, 301 reviewsSteps toTown/Bus Pet Ok/No Extra Fees! &Five Star
Jan. 26 – Feb. 2
Guesthouse in Stanfordville
4.92 out of 5 average rating, 164 reviewsEco Cottage in the Woods
Sep. 12 – 19
Guesthouse in Worcester
4.81 out of 5 average rating, 210 reviewsCarriage house apartment
Nov. 6 – 13
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