Guesthouse vacation rentals in Massachusetts
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Top-rated guesthouse rentals in 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 Massachusetts guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Shrewsbury
4.71 out of 5 average rating, 196 reviewsA Comfy Hilltop Home
Nov 14 – 21
Guesthouse in New Marlborough
4.91 out of 5 average rating, 180 reviewsCOZY GUESTHOUSE MINUTES AWAY FROM HIKING!
Aug 20 – 27
Guesthouse in Clarksburg
4.9 out of 5 average rating, 240 reviewsMountain Cottage Spectacular Views
May 30 – Jun 6
Guesthouse in Chilmark
4.98 out of 5 average rating, 198 reviewsBeautiful Guest House in Chilmark
Oct 22 – 29
Guesthouse in Gloucester
4.94 out of 5 average rating, 143 reviewsJestina's Cottage - Next to Rocky Neck
Oct 3 – 10
Guesthouse in Dedham
4.95 out of 5 average rating, 171 reviewsCountry Cottage in the City
Jul 26 – Aug 2
Guesthouse in Yarmouth
4.96 out of 5 average rating, 183 reviewsOne bedroom guest house on beautiful Cape Cod
Oct 4 – 11
Guesthouse in Wellfleet
4.97 out of 5 average rating, 180 reviewsAbundant Blessings Cottage-Wellfleet
May 7 – 14
Guest house rentals with a patio
Guesthouse in Williamstown
4.97 out of 5 average rating, 146 reviewsBrookside Cottage
Jul 25 – Aug 1
Guesthouse in Melrose
4.97 out of 5 average rating, 60 reviewsJimmy & Donny's AirBnB
Apr 1 – 8
Guesthouse in Marshfield
4.98 out of 5 average rating, 52 reviewsAdorable 1 bedroom guest house with ocean view
Oct 18 – 25
Guesthouse in Amesbury
4.93 out of 5 average rating, 87 reviewsTwo Penny Loft at Amesbury Farmhouse - Guest Suite
Apr 8 – 15
Guesthouse in Gloucester
4.91 out of 5 average rating, 34 reviewsThe Quarry
Mar 16 – 23
Guesthouse in Pittsfield
4.98 out of 5 average rating, 47 reviewsThe Nest at Birdland
Dec 24 – 31
Guesthouse in Braintree
4.71 out of 5 average rating, 28 reviewsThe Pool House
Aug 14 – 21
Guesthouse in Bourne
5.0 out of 5 average rating, 37 reviewsWaterfront Cottage / Your Cape Escape
Mar 20 – 27
Guest house rentals with a washer and dryer
Guesthouse in Cohasset
4.98 out of 5 average rating, 106 reviewsLovely 1 Bedroom Guest House. Downtown Cohasset
Oct 9 – 16
Guesthouse in Northampton
4.94 out of 5 average rating, 180 reviewsLittle Blue Studio
Oct 3 – 10
Guesthouse in Newton
4.93 out of 5 average rating, 211 reviewsCharming 2-story private Guesthouse
Oct 27 – Nov 3
Guesthouse in Worcester
4.81 out of 5 average rating, 209 reviewsCarriage house apartment
Nov 11 – 18
Guesthouse in North Adams
5.0 out of 5 average rating, 208 reviewsNetherwood - North Adams Guest House with Views
Dec 22 – 29
Guesthouse in Boston
4.99 out of 5 average rating, 232 reviewsThe Red Door Carriage House
Dec 27 – Jan 3
Guesthouse in Westford
4.98 out of 5 average rating, 80 reviewsDetached Waterfront Guest House
Nov 9 – 16
Guesthouse in Lexington
4.71 out of 5 average rating, 182 reviewsUnique Loft/ Studio Guesthouse (super convenient)
Jan 8 – 15
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