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
7–14 Dec
Bungalow in Easthampton
4.92 out of 5 average rating, 430 reviewsThe Creation Station
21–28 Jul
Home in Chatham
4.95 out of 5 average rating, 241 reviewsSlate House - a modern waterfront getaway
2–9 Jan
Home in Northampton
4.87 out of 5 average rating, 566 reviewsThe Farmhouse - Hot tub eclectic farmhouse 3 br
8–15 Sep
Apartment in Holliston
4.95 out of 5 average rating, 110 reviewsLake Link
9–16 Dec
Cabin in Becket
5.0 out of 5 average rating, 254 reviewsWaldtreff - quiet grand cabin
22–29 Dec
Home in Dennis
4.79 out of 5 average rating, 139 reviewsWalk2Beach, HotTub, FirePit, PetsOk
9–16 Oct
Cabin in Monterey
4.95 out of 5 average rating, 250 reviewsAmazing Berkshire Mountains Cabin
14–21 Jul
Family- and pet-friendly home rentals
Guest suite in Charlemont
4.9 out of 5 average rating, 182 reviewsUnique People & Pet-Welcoming Haven
11–18 Jul
Cabin in Cohasset
4.92 out of 5 average rating, 284 reviewsLionsgate at Cohasset
9–16 Oct
Guest suite in Montague
4.93 out of 5 average rating, 163 reviewsGreat Falls Private Suite
19–26 Dec
Apartment in Worcester
4.89 out of 5 average rating, 392 reviewsPrivate Suite with separate entrance in Worcester
7–14 Dec
Farm stay in Rutland
4.97 out of 5 average rating, 318 reviewsFarm Living
22–29 Sep
Cottage in Bernardston
4.88 out of 5 average rating, 286 reviewsCozy, Quiet Cottage on Country rd 2 mil from I-91
20–27 Mar
Home in Middleborough
4.94 out of 5 average rating, 295 reviewsPrivate retreat setting on 4 acres 1
13–20 Feb
Apartment in Concord
4.94 out of 5 average rating, 207 reviewsBishop Suite - Private suite in historic Concord
3–10 Mar
Family-friendly home rentals with a pool
Guesthouse in Dedham
4.95 out of 5 average rating, 171 reviewsCountry Cottage in the City
24 Jun – 1 Jul
Home in Plymouth
4.92 out of 5 average rating, 170 reviewsOur Secret Garden
14–21 Nov
Apartment in Winthrop
4.96 out of 5 average rating, 275 reviewsCody's Place Boston Airport Pool/Beaches ParkFree
3–10 Feb
Villa in Cambridge
4.99 out of 5 average rating, 188 reviewsPhil's Harvard & MIT Home
21–28 Aug
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
10–17 Sep
Apartment in Northampton
4.97 out of 5 average rating, 243 reviewsSunny Inspirit Apartment in best downtown location
17–24 Jul
Condo in Provincetown
4.97 out of 5 average rating, 189 reviewsP-Town Beach Beauty on the Bay. Water View!
1–8 Oct
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
23–30 Sep
Destinations to explore
- Family-friendly rentals United States
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