Guesthouse vacation rentals in Massachusetts
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Top-rated guesthouses in Massachusetts
Guests agree: these guesthouses are highly rated for location, cleanliness, and more.
Vacation 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
4.71 out of 5 average rating, 196 reviewsA Comfy Hilltop Home
Sep. 8 – 15
Guesthouse in Clarksburg
4.9 out of 5 average rating, 240 reviewsMountain Cottage Spectacular Views
Jul. 12 – 19
Guesthouse in New Marlborough
4.91 out of 5 average rating, 179 reviewsCOZY GUESTHOUSE MINUTES AWAY FROM HIKING!
Jul. 30 – Aug. 6
Guesthouse in Sagamore Beach
4.99 out of 5 average rating, 300 reviewsThe Guest House
Dec. 30 – Jan. 6
Guesthouse in North Truro
4.98 out of 5 average rating, 120 reviewsLight-filled North Truro cottage-Lovely gardens
Apr. 10 – 17
Guesthouse in Gloucester
4.94 out of 5 average rating, 143 reviewsJestina's Cottage - Next to Rocky Neck
Oct. 10 – 17
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
Aug. 2 – 9
Guesthouse in Yarmouth
4.96 out of 5 average rating, 183 reviewsOne bedroom guest house on beautiful Cape Cod
Nov. 1 – 8
Guesthouses 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
Apr. 24 – May 1
Guesthouse in Marshfield
4.98 out of 5 average rating, 52 reviewsAdorable 1 bedroom guest house with ocean view
Sep. 12 – 19
Guesthouse in Amesbury
4.93 out of 5 average rating, 87 reviewsTwo Penny Loft at Amesbury Farmhouse - Guest Suite
Jan. 17 – 24
Guesthouse in Bourne
5.0 out of 5 average rating, 37 reviewsWaterfront Cottage / Your Cape Escape
Mar. 25 – Apr. 1
Guesthouse in Gloucester
4.91 out of 5 average rating, 34 reviewsThe Quarry
Jan. 27 – Feb. 3
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 rentals with a washer and dryer
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
Sep. 29 – Oct. 6
Guesthouse in Worcester
4.81 out of 5 average rating, 209 reviewsCarriage house apartment
Oct. 22 – 29
Guesthouse in North Adams
5.0 out of 5 average rating, 208 reviewsNetherwood - North Adams Guest House with Views
Oct. 1 – 8
Guesthouse in Newton
4.93 out of 5 average rating, 211 reviewsCharming 2-story private Guesthouse
Oct. 26 – Nov. 2
Guesthouse in Boston
4.99 out of 5 average rating, 230 reviewsThe Red Door Carriage House
Aug. 29 – Sep. 5
Guesthouse in Westford
4.98 out of 5 average rating, 80 reviewsDetached Waterfront Guest House
Mar. 29 – Apr. 5
Guesthouse in Lexington
4.71 out of 5 average rating, 181 reviewsUnique Loft/ Studio Guesthouse (super convenient)
Dec. 8 – 15
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