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
4.72 out of 5 average rating, 197 reviewsA Comfy Hilltop Home
Jan 10 – 17
Guesthouse in New Marlborough
4.91 out of 5 average rating, 180 reviewsCOZY GUESTHOUSE MINUTES AWAY FROM HIKING!
Jan 3 – 10
Guesthouse in Clarksburg
4.9 out of 5 average rating, 240 reviewsMountain Cottage Spectacular Views
Feb 11 – 18
Guesthouse in Sagamore Beach
4.99 out of 5 average rating, 300 reviewsThe Guest House
Jun 21 – 28
Guesthouse in Chilmark
4.98 out of 5 average rating, 198 reviewsBeautiful Guest House in Chilmark
Jun 6 – 13
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
Jul 30 – Aug 6
Guesthouse in Yarmouth
4.96 out of 5 average rating, 183 reviewsOne bedroom guest house on beautiful Cape Cod
Oct 15 – 22
Guesthouse in Gloucester
4.94 out of 5 average rating, 143 reviewsJestina's Cottage - Next to Rocky Neck
Sep 29 – Oct 6
Guest house rentals with a patio
Guesthouse in Williamstown
4.97 out of 5 average rating, 147 reviewsBrookside Cottage
Aug 25 – Sep 1
Guesthouse in Marshfield
4.98 out of 5 average rating, 53 reviewsAdorable 1 bedroom guest house with ocean view
Nov 24 – Dec 1
Guesthouse in Melrose
4.97 out of 5 average rating, 60 reviewsJimmy & Donny's AirBnB
Apr 26 – May 3
Guesthouse in Amesbury
4.93 out of 5 average rating, 88 reviewsTwo Penny Loft at Amesbury Farmhouse - Guest Suite
Dec 16 – 23
Guesthouse in Braintree
4.72 out of 5 average rating, 29 reviewsThe Pool House
Aug 7 – 14
Guesthouse in Gloucester
4.91 out of 5 average rating, 34 reviewsThe Quarry
Oct 15 – 22
Guesthouse in Bourne
5.0 out of 5 average rating, 37 reviewsWaterfront Cottage / Your Cape Escape
Sep 18 – 25
Guesthouse in Pittsfield
4.98 out of 5 average rating, 47 reviewsThe Nest at Birdland
Dec 26 – Jan 2
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
May 9 – 16
Guesthouse in Rockport
5.0 out of 5 average rating, 215 reviewsSea Mist Cottage Rockport, MA
Sep 12 – 19
Guesthouse in North Adams
5.0 out of 5 average rating, 209 reviewsNetherwood - North Adams Guest House with Views
Dec 22 – 29
Guesthouse in Newton
4.93 out of 5 average rating, 211 reviewsCharming 2-story private Guesthouse
Oct 7 – 14
Guesthouse in Worcester
4.81 out of 5 average rating, 210 reviewsCarriage house apartment
Jan 12 – 19
Guesthouse in Boston
4.99 out of 5 average rating, 233 reviewsThe Red Door Carriage House
Nov 11 – 18
Guesthouse in Westford
4.98 out of 5 average rating, 80 reviewsDetached Waterfront Guest House
Aug 28 – Sep 4
Guesthouse in Lexington
4.71 out of 5 average rating, 182 reviewsUnique Loft/ Studio Guesthouse (super convenient)
Dec 3 – 10
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