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Guesthouse holiday rentals in Massachusetts
Find and book unique guesthouse rentals on Airbnb
Top-rated Guesthouses in Massachusetts
Guests agree: These guesthouses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Massachusetts guesthouses
Family-Friendly guesthouses
![](https://a0.muscache.com/im/pictures/49236450-174c-4c20-a702-5b03e5c04a8b.jpg?im_w=720)
Guesthouse in Shrewsbury
4.72 out of 5 average rating, 204 reviewsA Comfy Hilltop Home
![](https://a0.muscache.com/im/pictures/hosting/Hosting-U3RheVN1cHBseUxpc3Rpbmc6NTQwNjUz/original/1ef051c4-35ce-4593-a126-4d2e4a0a4857.jpeg?im_w=720)
Guesthouse in Northampton
4.92 out of 5 average rating, 248 reviewsLarge Studio – Walk to Town
![](https://a0.muscache.com/im/pictures/a7a9f85e-f05b-4a38-82a6-dc9728682c0f.jpg?im_w=720)
Guesthouse in New Marlborough
4.91 out of 5 average rating, 185 reviewsCOZY GUESTHOUSE MINUTES AWAY FROM HIKING!
![](https://a0.muscache.com/im/pictures/85b886f7-2a3f-431b-8f95-7d2092708ea5.jpg?im_w=720)
Guesthouse in Becket
4.93 out of 5 average rating, 263 reviewsCountry Cabin
![](https://a0.muscache.com/im/pictures/78b50d2d-4204-4fda-b8b1-e7aaa0c1aa11.jpg?im_w=720)
Guesthouse in Williamstown
4.93 out of 5 average rating, 227 reviewsPerfect Base for Your Berkshire Adventure
![](https://a0.muscache.com/im/pictures/miso/Hosting-13121970/original/3c897d20-e846-4921-af1b-0e6debbdbc78.jpeg?im_w=720)
Guesthouse in Sagamore Beach
4.99 out of 5 average rating, 309 reviewsThe Guest House
![](https://a0.muscache.com/im/pictures/4368b30b-f7f6-4093-9f68-b758e0ab7655.jpg?im_w=720)
Guesthouse in Yarmouth
4.96 out of 5 average rating, 197 reviewsOne bedroom guest house on beautiful Cape Cod
![](https://a0.muscache.com/im/pictures/b368a125-18da-4dd3-befc-8cb611a48015.jpg?im_w=720)
Guesthouse in Chilmark
4.98 out of 5 average rating, 205 reviewsBeautiful Guest House in Chilmark
Guesthouses with a patio
![](https://a0.muscache.com/im/pictures/miso/Hosting-50769924/original/cdb63151-b384-48d6-89f1-b3c804204361.jpeg?im_w=720)
Guesthouse in Williamstown
4.96 out of 5 average rating, 157 reviewsBrookside Cottage
![](https://a0.muscache.com/im/pictures/hosting/Hosting-1048715381327431881/original/8520b628-454e-435a-a2e0-a82516b7d844.jpeg?im_w=720)
Guesthouse in Brewster
5 out of 5 average rating, 37 reviewsBrand new, on a swimmable pond
![](https://a0.muscache.com/im/pictures/miso/Hosting-52963970/original/294e5824-531d-43f3-8944-2c4f559c43b9.jpeg?im_w=720)
Guesthouse in Amesbury
4.94 out of 5 average rating, 96 reviewsTwo Penny Loft at Amesbury Farmhouse - Guest Suite
![](https://a0.muscache.com/im/pictures/miso/Hosting-794043626040602984/original/2b308ede-7f62-4f68-8d67-9bd52ac11d99.jpeg?im_w=720)
Guesthouse in Melrose
4.97 out of 5 average rating, 74 reviewsJimmy & Donny's AirBnB
![](https://a0.muscache.com/im/pictures/miso/Hosting-611758890996801803/original/ca7b5479-7f1b-44cc-9b79-e56c913a4434.jpeg?im_w=720)
Guesthouse in Marshfield
4.98 out of 5 average rating, 61 reviewsAdorable 1 bedroom guest house with ocean view
![](https://a0.muscache.com/im/pictures/miso/Hosting-50678433/original/06ff205a-21f4-4603-ab9b-58c6add237cc.jpeg?im_w=720)
Guesthouse in Bourne
5 out of 5 average rating, 48 reviewsWaterfront Cottage / Your Cape Escape
![](https://a0.muscache.com/im/pictures/airflow/Hosting-51462193/original/d5410f72-0ef9-4468-856b-fa1918d5e528.jpg?im_w=720)
Guesthouse in Gloucester
4.93 out of 5 average rating, 44 reviewsCharming Guesthouse with Access to Private Beach
![](https://a0.muscache.com/im/pictures/miso/Hosting-808839351078014427/original/268c1978-d490-45a6-ad6a-6b70bbade568.jpeg?im_w=720)
Guesthouse in Pittsfield
4.95 out of 5 average rating, 60 reviewsThe Nest at Birdland
Guest house rentals with a washing machine and dryer
![](https://a0.muscache.com/im/pictures/4f6bb85d-03b3-44ff-a3eb-f9be3425dbbc.jpg?im_w=720)
Guesthouse in Cohasset
4.98 out of 5 average rating, 114 reviewsLovely 1 Bedroom Guest House. Downtown Cohasset
![](https://a0.muscache.com/im/pictures/6616e7a0-7d13-4ce2-a40f-a3f8a82243df.jpg?im_w=720)
Guesthouse in Stockbridge
4.91 out of 5 average rating, 102 reviewsModern barn in the heart of the Berkshires
![](https://a0.muscache.com/im/pictures/miso/Hosting-40805311/original/8fc4d42b-bab8-442c-a77c-a80ddbb6ad0d.jpeg?im_w=720)
Guesthouse in Westford
4.98 out of 5 average rating, 87 reviewsDetached Waterfront Guest House
![](https://a0.muscache.com/im/pictures/miso/Hosting-991951831362747647/original/0568e404-6f2c-49b7-a69e-c961e60f2226.png?im_w=720)
Guesthouse in Duxbury
5 out of 5 average rating, 5 reviewsDuxbury Getaway! Location+Charm!
![](https://a0.muscache.com/im/pictures/miso/Hosting-713600087568109117/original/b47e5d7d-e00f-49e4-a4df-d7a41530764b.jpeg?im_w=720)
Guesthouse in Abington
5 out of 5 average rating, 60 reviewsCozy In-Law Apartment
![](https://a0.muscache.com/im/pictures/miso/Hosting-862961933370542032/original/eae2b565-16d1-4564-94f1-4afaf6f5c0f2.jpeg?im_w=720)
Guesthouse in Winchendon
5 out of 5 average rating, 30 reviewsCopley’s Guest House on Lake Monomonac
![](https://a0.muscache.com/im/pictures/c6b4eec7-0275-41b6-b3e0-fdaea269cefb.jpg?im_w=720)
Guesthouse in Lenox
4.91 out of 5 average rating, 57 reviewsLenox - Sunny cottage nestled in the garden
![](https://a0.muscache.com/im/pictures/hosting/Hosting-21921947/original/3a52e156-185f-4dfb-9099-8e9fef5d5541.jpeg?im_w=720)
Guesthouse in Gloucester
4.96 out of 5 average rating, 73 reviewsPlum Cove Cottage with king suite!
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