Guesthouse holiday rentals in Massachusetts
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Top-rated Guesthouses in Massachusetts
Guests agree: These guesthouses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Massachusetts guesthouses
Family-Friendly guesthouses
Guesthouse in Shrewsbury
4.72 out of 5 average rating, 198 reviewsA Comfy Hilltop Home
Guesthouse in Brewster
4.94 out of 5 average rating, 216 reviewsCharming Antique Cape Cod Cottage
Guesthouse in New Marlborough
4.91 out of 5 average rating, 181 reviewsCOZY GUESTHOUSE MINUTES AWAY FROM HIKING!
Guesthouse in Clarksburg
4.9 out of 5 average rating, 241 reviewsMountain Cottage Spectacular Views
Guesthouse in Sagamore Beach
4.99 out of 5 average rating, 300 reviewsThe Guest House
Guesthouse in Yarmouth
4.96 out of 5 average rating, 186 reviewsOne bedroom guest house on beautiful Cape Cod
Guesthouse in Chilmark
4.98 out of 5 average rating, 199 reviewsBeautiful Guest House in Chilmark
Guesthouse in Wellfleet
4.97 out of 5 average rating, 181 reviewsAbundant Blessings Cottage-Wellfleet
Guesthouses with a patio
Guesthouse in Williamstown
4.97 out of 5 average rating, 151 reviewsBrookside Cottage
Guesthouse in Melrose
4.97 out of 5 average rating, 65 reviewsJimmy & Donny's AirBnB
Guesthouse in Lowell
5.0 out of 5 average rating, 7 reviewsPrivate guest house
Guesthouse in Marshfield
4.98 out of 5 average rating, 56 reviewsAdorable 1 bedroom guest house with ocean view
Guesthouse in Pittsfield
4.98 out of 5 average rating, 47 reviewsThe Nest at Birdland
Guesthouse in Amesbury
4.93 out of 5 average rating, 91 reviewsTwo Penny Loft at Amesbury Farmhouse - Guest Suite
Guesthouse in Brewster
5.0 out of 5 average rating, 20 reviewsBrand new, on a swimmable pond
Guesthouse in Gloucester
4.91 out of 5 average rating, 35 reviewsThe Quarry
Guest house rentals with a washing machine and dryer
Guesthouse in Newton
4.93 out of 5 average rating, 215 reviewsCharming 2-story private Guesthouse
Guesthouse in Cohasset
4.98 out of 5 average rating, 107 reviewsLovely 1 Bedroom Guest House. Downtown Cohasset
Guesthouse in Northampton
4.94 out of 5 average rating, 182 reviewsLittle Blue Studio
Guesthouse in North Adams
5.0 out of 5 average rating, 213 reviewsNetherwood - North Adams Guest House with Views
Guesthouse in Worcester
4.81 out of 5 average rating, 217 reviewsCarriage house apartment
Guesthouse in Boston
4.99 out of 5 average rating, 238 reviewsThe Red Door Carriage House
Guesthouse in Westford
4.98 out of 5 average rating, 82 reviewsDetached Waterfront Guest House
Guesthouse in Wendell
5.0 out of 5 average rating, 20 reviewsQuiet Country Home in Wendell
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