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Family-friendly vacation rentals in Chilmark
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Chilmark
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 Chilmark family-friendly rentals
Family-friendly home rentals with a hot tub
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Home in West Dennis
4.8 out of 5 average rating, 144 reviewsWalk2Beach, HotTub, FirePit, PetsOk
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Home in Centerville, Barnstable
4.97 out of 5 average rating, 145 reviewsLuxury House 0.25 mi from Craigville Beach
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Home in Edgartown
4.99 out of 5 average rating, 71 reviewsContemporary Edgartown Beauty: The Perfect Retreat
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Home in Edgartown
5 out of 5 average rating, 49 reviewsOn HGTV! Gorgeous, AC, Hot Tub, WALK Town & Beach
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Guesthouse in Oak Bluffs
4.99 out of 5 average rating, 80 reviewsMermaid Cottage
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Home in East Falmouth
4.89 out of 5 average rating, 57 reviewsPeaceful waterfront home with dock/ hot tub
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Home in Dennis
4.91 out of 5 average rating, 43 reviewsCape Cod Lakefront Home
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Condo in Brewster
4.95 out of 5 average rating, 19 reviewsEscape to the Cape
Family- and pet-friendly home rentals
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Home in Yarmouth Port
4.99 out of 5 average rating, 318 reviewsFabulous Waterfront! 3bdrm/2bth Kayaks & Firepit
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Home in West Tisbury
4.86 out of 5 average rating, 108 reviewsSweet 3BR Cape in West Tisbury, MV
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Cottage in East Falmouth
4.91 out of 5 average rating, 340 reviewsAccess to Great Pond, 2 Kayaks
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Cottage in Sandwich
4.87 out of 5 average rating, 317 reviewsOceanfront Cape Cod Cottage w/Private Beach ~ Pets
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Guesthouse in Sagamore Beach
4.99 out of 5 average rating, 304 reviewsThe Guest House
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Condo in Newport
4.92 out of 5 average rating, 506 reviewsBoutique Hotel Special pricing available
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Tiny home in Dennis Port
4.81 out of 5 average rating, 444 reviews★TINY HOUSE★4/10mi Beach & Village★Pet OK★2 Bikes
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Guesthouse in Tisbury
4.85 out of 5 average rating, 233 reviewsAdorable Vineyard Haven Cottage
Family-friendly home rentals with a pool
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Home in Aquinnah
5 out of 5 average rating, 3 reviewsNine Acres Secluded Escape
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Home in Cotuit
4.93 out of 5 average rating, 15 reviewsShoestringBayHouse, waterfront & pool in Cotuit
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Guest suite in Little Compton
4.93 out of 5 average rating, 90 reviewsBrimstone Hill Farm, Little Compton, RI
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Condo in Vineyard Haven
5 out of 5 average rating, 17 reviewsRelax....You're on Island Time......
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Condo in Tisbury
4.91 out of 5 average rating, 45 reviewsPrivate 3bdrm Condo Tashmoo Woods
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Rental unit in Hyannis Port
4.82 out of 5 average rating, 45 reviews1 bdrm 4ppl apartment,stairs,pool,no meals,deck
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Home in Cotuit
4.94 out of 5 average rating, 100 reviewsPrivate Pool, near beaches, 3 BR/3 BA, Central Air
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Home in East Falmouth
4.93 out of 5 average rating, 15 reviewsGorgeous Cape Cod Property!
Quick stats about vacation rentals that are family-friendly in Chilmark
Total rentals
160 properties
Wifi availability
160 properties include access to wifi
Rentals with dedicated workspaces
90 properties have a dedicated workspace
Pet-friendly rentals
60 properties allow pets
Total number of reviews
2K reviews
Nightly prices starting at
$140 before taxes and fees
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