Family-friendly holiday rentals in Massachusetts
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Massachusetts
Guests agree: these family-friendly homes 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 family-friendly rentals
Family-friendly home rentals with a hot tub
Home in Chester
4.96 out of 5 average rating, 311 reviewsRiverfront Getaway
30 Jul – 6 Aug
Bungalow in Easthampton
4.92 out of 5 average rating, 430 reviewsThe Creation Station
21–26 Jul
Home in Chatham
4.95 out of 5 average rating, 241 reviewsSlate House - a modern waterfront getaway
18–25 Feb
Cabin in Becket
5.0 out of 5 average rating, 254 reviewsWaldtreff - quiet grand cabin
20–27 Dec
Flat in Holliston
4.95 out of 5 average rating, 110 reviewsLake Link
14–21 Sep
Home in Northampton
4.87 out of 5 average rating, 566 reviewsThe Farmhouse - Hot tub eclectic farmhouse 3 br
8–15 Sep
Home in Dennis
4.79 out of 5 average rating, 139 reviewsWalk2Beach, HotTub, FirePit, PetsOk
26 Jan – 2 Feb
Cabin in Monterey
4.95 out of 5 average rating, 250 reviewsAmazing Berkshire Mountains Cabin
5–12 Jun
Family- and pet-friendly home rentals
Cabin in Cohasset
4.92 out of 5 average rating, 284 reviewsLionsgate at Cohasset
13–20 Oct
Cottage in Bernardston
4.88 out of 5 average rating, 286 reviewsCozy, Quiet Cottage on Country rd 2 mil from I-91
25 Mar – 1 Apr
Guest suite in Montague
4.93 out of 5 average rating, 163 reviewsGreat Falls Private Suite
26 Aug – 2 Sep
Home in Middleborough
4.94 out of 5 average rating, 295 reviewsPrivate retreat setting on 4 acres 1
26 Feb – 5 Mar
Barn in Carlisle
4.84 out of 5 average rating, 513 reviews✨Entire Secluded Barn Suite Ctr Historic Carlisle✨
10–17 Feb
Farm stay in Rutland
4.97 out of 5 average rating, 317 reviewsFarm Living
27 Dec – 3 Jan
Tiny home in Dennis Port
4.81 out of 5 average rating, 437 reviews★TINY HOUSE★4/10mi Beach & Village★Pet OK★2 Bikes
1–8 Mar
Flat in Worcester
4.89 out of 5 average rating, 392 reviewsPrivate Suite with separate entrance in Worcester
6–13 Dec
Family-friendly home rentals with a pool
Guest house in Dedham
4.95 out of 5 average rating, 171 reviewsCountry Cottage in the City
24 Jun – 1 Jul
Flat in Winthrop
4.96 out of 5 average rating, 275 reviewsCody's Place Boston Airport Pool/Beaches ParkFree
26 Mar – 2 Apr
Home in Plymouth
4.92 out of 5 average rating, 170 reviewsOur Secret Garden
2–9 Nov
Villa in Cambridge
4.99 out of 5 average rating, 188 reviewsPhil's Harvard & MIT Home
18–25 Aug
Flat in Northampton
4.97 out of 5 average rating, 243 reviewsSunny Inspirit Apartment in best downtown location
17–24 Jul
Guest house in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
8–15 Sep
Apartment in Provincetown
4.97 out of 5 average rating, 189 reviewsP-Town Beach Beauty on the Bay. Water View!
2–9 Dec
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
4–11 Dec
Destinations to explore
- Family-friendly rentals United States
- Family-friendly rentals Boston
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