Guest house holiday rentals in Massachusetts
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Top-rated guest house rentals in Massachusetts
Guests agree: these guest house rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for guest house rentals in Massachusetts
Family-friendly guest house rentals
Guest house in Shrewsbury
4.71 out of 5 average rating, 196 reviewsA Comfy Hilltop Home
8–15 Sept
Guest house in Clarksburg
4.9 out of 5 average rating, 240 reviewsMountain Cottage Spectacular Views
12–19 Jul
Guest house in New Marlborough
4.91 out of 5 average rating, 179 reviewsCOZY GUESTHOUSE MINUTES AWAY FROM HIKING!
29 Jul – 5 Aug
Guest house in Sagamore Beach
4.99 out of 5 average rating, 300 reviewsThe Guest House
30 Dec – 6 Jan
Guest house in Gloucester
4.94 out of 5 average rating, 143 reviewsJestina's Cottage - Next to Rocky Neck
10–17 Oct
Guest house in North Truro
4.98 out of 5 average rating, 120 reviewsLight-filled North Truro cottage-Lovely gardens
10–17 Apr
Guest house in Yarmouth
4.96 out of 5 average rating, 183 reviewsOne bedroom guest house on beautiful Cape Cod
31 Oct – 7 Nov
Guest house in Chilmark
4.98 out of 5 average rating, 198 reviewsBeautiful Guest House in Chilmark
11–18 Dec
Guest house rentals with a patio
Guest house in Williamstown
4.97 out of 5 average rating, 146 reviewsBrookside Cottage
25 Aug – 1 Sept
Guest house in Melrose
4.97 out of 5 average rating, 59 reviewsJimmy & Donny's AirBnB
24 Apr – 1 May
Guest house in Marshfield
4.98 out of 5 average rating, 51 reviewsAdorable 1 bedroom guest house with ocean view
21–28 Aug
Guest house in Amesbury
4.93 out of 5 average rating, 87 reviewsTwo Penny Loft at Amesbury Farmhouse - Guest Suite
17–24 Jan
Guest house in Braintree
4.7 out of 5 average rating, 27 reviewsThe Pool House
13–20 Aug
Guest house in Bourne
5.0 out of 5 average rating, 37 reviewsWaterfront Cottage / Your Cape Escape
25 Mar – 1 Apr
Guest house in Gloucester
4.91 out of 5 average rating, 34 reviewsThe Quarry
29 May – 5 Jun
Guest house in Rehoboth
5.0 out of 5 average rating, 42 reviewsRustic Cottage a Rural Rehoboth Getaway
25 Aug – 1 Sept
Guest house rentals with a washing machine and dryer
Guest house in Cohasset
4.98 out of 5 average rating, 105 reviewsLovely 1 Bedroom Guest House. Downtown Cohasset
10–17 Oct
Guest house in Northampton
4.94 out of 5 average rating, 178 reviewsLittle Blue Studio
16–23 Oct
Guest house in Worcester
4.81 out of 5 average rating, 208 reviewsCarriage house apartment
26 Dec – 2 Jan
Guest house in North Adams
5.0 out of 5 average rating, 207 reviewsNetherwood - North Adams Guest House with Views
1–8 Oct
Guest house in Newton
4.93 out of 5 average rating, 211 reviewsCharming 2-story private Guesthouse
7–14 Sept
Guest house in Boston
4.99 out of 5 average rating, 230 reviewsThe Red Door Carriage House
6–13 Dec
Guest house in Westford
4.98 out of 5 average rating, 80 reviewsDetached Waterfront Guest House
29 Mar – 5 Apr
Guest house in Lexington
4.71 out of 5 average rating, 180 reviewsUnique Loft/ Studio Guesthouse (super convenient)
29 Nov – 6 Dec
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