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
Jan 1 – 8
Guesthouse in Clarksburg
4.9 out of 5 average rating, 240 reviewsMountain Cottage Spectacular Views
Apr 15 – 22
Guesthouse in New Marlborough
4.91 out of 5 average rating, 179 reviewsCOZY GUESTHOUSE MINUTES AWAY FROM HIKING!
Aug 21 – 28
Guesthouse in Sagamore Beach
4.99 out of 5 average rating, 300 reviewsThe Guest House
Jan 1 – 8
Guesthouse in North Truro
4.98 out of 5 average rating, 120 reviewsLight-filled North Truro cottage-Lovely gardens
Nov 16 – 23
Guesthouse in Chilmark
4.98 out of 5 average rating, 198 reviewsBeautiful Guest House in Chilmark
Oct 11 – 18
Guesthouse in Gloucester
4.94 out of 5 average rating, 143 reviewsJestina's Cottage - Next to Rocky Neck
Oct 2 – 9
Guesthouse in Yarmouth
4.96 out of 5 average rating, 183 reviewsOne bedroom guest house on beautiful Cape Cod
Nov 2 – 9
Guest house rentals with a patio
Guesthouse in Williamstown
4.97 out of 5 average rating, 146 reviewsBrookside Cottage
Aug 12 – 19
Guesthouse in Melrose
4.97 out of 5 average rating, 59 reviewsJimmy & Donny's AirBnB
Mar 24 – 31
Guesthouse in Marshfield
4.98 out of 5 average rating, 52 reviewsAdorable 1 bedroom guest house with ocean view
Sep 26 – Oct 3
Guesthouse in Amesbury
4.93 out of 5 average rating, 87 reviewsTwo Penny Loft at Amesbury Farmhouse - Guest Suite
Mar 25 – Apr 1
Guesthouse in Bourne
5.0 out of 5 average rating, 37 reviewsWaterfront Cottage / Your Cape Escape
Dec 24 – 31
Guesthouse in Gloucester
4.91 out of 5 average rating, 34 reviewsThe Quarry
Mar 1 – 8
Guesthouse in Rehoboth
5.0 out of 5 average rating, 42 reviewsRustic Cottage a Rural Rehoboth Getaway
Aug 25 – Sep 1
Guesthouse in Braintree
4.7 out of 5 average rating, 27 reviewsThe Pool House
Jun 22 – 29
Guest house rentals with a washer and dryer
Guesthouse in Worcester
4.81 out of 5 average rating, 209 reviewsCarriage house apartment
Jun 9 – 16
Guesthouse in Rockport
5.0 out of 5 average rating, 214 reviewsSea Mist Cottage Rockport, MA
Oct 22 – 29
Guesthouse in Northampton
4.94 out of 5 average rating, 178 reviewsLittle Blue Studio
Jul 9 – 16
Guesthouse in North Adams
5.0 out of 5 average rating, 208 reviewsNetherwood - North Adams Guest House with Views
Nov 23 – 30
Guesthouse in Newton
4.93 out of 5 average rating, 211 reviewsCharming 2-story private Guesthouse
Oct 18 – 25
Guesthouse in Boston
4.99 out of 5 average rating, 230 reviewsThe Red Door Carriage House
Jan 3 – 10
Guesthouse in Westford
4.98 out of 5 average rating, 80 reviewsDetached Waterfront Guest House
Aug 20 – 27
Guesthouse in Lexington
4.71 out of 5 average rating, 181 reviewsUnique Loft/ Studio Guesthouse (super convenient)
Nov 9 – 16
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