Family-friendly vacation rentals in Massachusetts
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Top-rated family-friendly rentals in Massachusetts
Guests agree: these family-friendly homes 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 family-friendly rentals
Family-friendly home rentals with a hot tub
Home in Chester
4.96 out of 5 average rating, 312 reviewsRiverfront Getaway
Oct 14 – 21
Home in Chatham
4.95 out of 5 average rating, 241 reviewsSlate House - a modern waterfront getaway
Nov 16 – 23
Bungalow in Easthampton
4.92 out of 5 average rating, 433 reviewsThe Creation Station
Jul 23 – 30
Home in Northampton
4.87 out of 5 average rating, 567 reviewsThe Farmhouse - Hot tub eclectic farmhouse 3 br
Sep 8 – 15
Home in Dennis
4.79 out of 5 average rating, 140 reviewsWalk2Beach, HotTub, FirePit, PetsOk
Feb 16 – 23
Apartment in Holliston
4.95 out of 5 average rating, 110 reviewsLake Link
Dec 25 – Jan 1
Home in North Andover
4.94 out of 5 average rating, 127 reviewsNana-tucket Inn
Jan 10 – 17
Cabin in Monterey
4.95 out of 5 average rating, 251 reviewsAmazing Berkshire Mountains Cabin
Aug 5 – 12
Family- and pet-friendly home rentals
Cottage in Bernardston
4.88 out of 5 average rating, 287 reviewsCozy, Quiet Cottage on Country rd 2 mil from I-91
Nov 3 – 10
Barn in Carlisle
4.84 out of 5 average rating, 513 reviews✨Entire Secluded Barn Suite Ctr Historic Carlisle✨
Feb 18 – 25
Guest suite in Charlemont
4.9 out of 5 average rating, 183 reviewsUnique People & Pet-Welcoming Haven
Apr 20 – 27
Farm stay in Rutland
4.97 out of 5 average rating, 318 reviewsFarm Living
Aug 5 – 12
Apartment in Worcester
4.89 out of 5 average rating, 393 reviewsPrivate Suite with separate entrance in Worcester
Feb 7 – 14
Home in Middleborough
4.94 out of 5 average rating, 296 reviewsPrivate retreat setting on 4 acres 1
Apr 7 – 14
Apartment in Natick
4.98 out of 5 average rating, 333 reviewsScandi-Modern Apartment
Oct 24 – 31
Home in Feeding Hills
4.89 out of 5 average rating, 886 reviewsFarm Fresh Feeding Hills
Sep 15 – 22
Family-friendly home rentals with a pool
Home in Plymouth
4.92 out of 5 average rating, 170 reviewsOur Secret Garden
Feb 4 – 11
Apartment in Winthrop
4.96 out of 5 average rating, 276 reviewsCody's Place Boston Airport Pool/Beaches ParkFree
Oct 29 – Nov 5
Guesthouse in Dedham
4.95 out of 5 average rating, 171 reviewsCountry Cottage in the City
Jul 26 – Aug 2
Villa in Cambridge
4.99 out of 5 average rating, 188 reviewsPhil's Harvard & MIT Home
Oct 8 – 15
Apartment in Northampton
4.97 out of 5 average rating, 243 reviewsSunny Inspirit Apartment in best downtown location
Oct 11 – 18
Home in Barnstable
4.93 out of 5 average rating, 104 reviewsMagical pool home with windmill/new kitchen
Nov 4 – 11
Condo in Provincetown
4.97 out of 5 average rating, 191 reviewsP-Town Beach Beauty on the Bay. Water View!
Oct 17 – 24
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
Aug 30 – Sep 6
Destinations to explore
- Family-friendly rentals United States
- Family-friendly rentals Boston
- Villa rentals Massachusetts
- Farmstay rentals Massachusetts
- Townhouse rentals Massachusetts
- Cabin rentals Massachusetts
- Rentals with pools Massachusetts
- Rentals with lake access Massachusetts
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- Loft rentals Massachusetts
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- Wheelchair accessible rentals Massachusetts
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- Cottage rentals Massachusetts
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- Family-friendly rentals Cape Cod
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