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
Jun 9 – 16
Guesthouse in Dedham
4.95 out of 5 average rating, 171 reviewsCountry Cottage in the City
Jun 5 – 12
Guesthouse in New Marlborough
4.91 out of 5 average rating, 179 reviewsCOZY GUESTHOUSE MINUTES AWAY FROM HIKING!
Oct 14 – 21
Guesthouse in Sagamore Beach
4.99 out of 5 average rating, 300 reviewsThe Guest House
Dec 5 – 12
Guesthouse in Clarksburg
4.9 out of 5 average rating, 240 reviewsMountain Cottage Spectacular Views
Jul 12 – 19
Guesthouse in Gloucester
4.94 out of 5 average rating, 143 reviewsJestina's Cottage - Next to Rocky Neck
Oct 11 – 18
Guesthouse in Yarmouth
4.96 out of 5 average rating, 183 reviewsOne bedroom guest house on beautiful Cape Cod
Mar 21 – 28
Guesthouse in Chilmark
4.98 out of 5 average rating, 198 reviewsBeautiful Guest House in Chilmark
Oct 29 – Nov 5
Guest house rentals with a patio
Guesthouse in Williamstown
4.97 out of 5 average rating, 146 reviewsBrookside Cottage
Aug 25 – Sep 1
Guesthouse in Melrose
4.97 out of 5 average rating, 59 reviewsJimmy & Donny's AirBnB
Mar 29 – Apr 5
Guesthouse in Marshfield
4.98 out of 5 average rating, 51 reviewsAdorable 1 bedroom guest house with ocean view
Dec 28 – Jan 4
Guesthouse in Amesbury
4.93 out of 5 average rating, 87 reviewsTwo Penny Loft at Amesbury Farmhouse - Guest Suite
Mar 3 – 10
Guesthouse in Braintree
4.7 out of 5 average rating, 27 reviewsThe Pool House
Aug 13 – 20
Guesthouse in Rehoboth
5.0 out of 5 average rating, 42 reviewsRustic Cottage a Rural Rehoboth Getaway
Aug 25 – Sep 1
Guesthouse in Bourne
5.0 out of 5 average rating, 37 reviewsWaterfront Cottage / Your Cape Escape
Mar 11 – 18
Guesthouse in Brewster
5.0 out of 5 average rating, 14 reviewsBrand new, on a swimmable pond
Jan 14 – 21
Guest house rentals with a washer and dryer
Guesthouse in Cohasset
4.98 out of 5 average rating, 105 reviewsLovely 1 Bedroom Guest House. Downtown Cohasset
May 6 – 13
Guesthouse in Northampton
4.94 out of 5 average rating, 178 reviewsLittle Blue Studio
Jul 9 – 16
Guesthouse in Worcester
4.81 out of 5 average rating, 207 reviewsCarriage house apartment
Mar 13 – 20
Guesthouse in North Adams
5.0 out of 5 average rating, 207 reviewsNetherwood - North Adams Guest House with Views
Sep 30 – Oct 7
Guesthouse in Newton
4.93 out of 5 average rating, 211 reviewsCharming 2-story private Guesthouse
Sep 7 – 14
Guesthouse in Boston
4.99 out of 5 average rating, 230 reviewsThe Red Door Carriage House
Dec 2 – 9
Guesthouse in Westford
4.98 out of 5 average rating, 80 reviewsDetached Waterfront Guest House
Apr 15 – 22
Guesthouse in Lexington
4.71 out of 5 average rating, 180 reviewsUnique Loft/ Studio Guesthouse (super convenient)
Sep 19 – 26
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