Family-friendly holiday 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.
Holiday 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
Home in Dennis
4.79 out of 5 average rating, 140 reviewsWalk2Beach, HotTub, FirePit, PetsOk
16–23 Feb
Apartment in Oak Bluffs
4.92 out of 5 average rating, 128 reviewsVictorian Oasis: Driveway, hot tub, grill & more
15–22 Jan
Home in Centerville, Barnstable
4.97 out of 5 average rating, 142 reviewsLuxury House 0.25 mi from Craigville Beach
9–16 Apr
Home in Edgartown
4.99 out of 5 average rating, 68 reviewsContemporary Edgartown Beauty: The Perfect Retreat
13–20 Feb
Home in Edgartown
5.0 out of 5 average rating, 47 reviewsOn HGTV! Gorgeous, AC, Hot Tub, WALK Town & Beach
25 Oct – 1 Nov
Guesthouse in Oak Bluffs
4.99 out of 5 average rating, 73 reviewsMermaid Cottage
23 Feb – 2 Mar
Home in Falmouth
4.89 out of 5 average rating, 57 reviewsPeaceful waterfront home with dock/ hot tub
26 Apr – 3 May
Home in Dennis
4.91 out of 5 average rating, 43 reviewsCape Cod Lakefront Home
8–15 Jun
Family- and pet-friendly home rentals
Guesthouse in Tisbury
4.86 out of 5 average rating, 227 reviewsAdorable Vineyard Haven Cottage
10–17 Oct
Cottage in Sandwich
4.87 out of 5 average rating, 307 reviewsOceanfront Cottage w/Private Beach ~ Lil’ Sea Sass
16–23 Jan
Guesthouse in Sagamore Beach
4.99 out of 5 average rating, 300 reviewsThe Guest House
17–24 Dec
Home in West Tisbury
4.86 out of 5 average rating, 107 reviewsSweet 3BR Cape in West Tisbury, MV
19–26 Dec
Home in Yarmouth Port, Cape Cod
4.99 out of 5 average rating, 312 reviewsFabulous Waterfront! 3bdrm/2bth Kayaks & Firepit
21–28 Dec
Condo in Newport
4.92 out of 5 average rating, 483 reviewsBoutique Hotel Special pricing available
16–23 Sep
Home in Sandwich
4.93 out of 5 average rating, 195 reviewsCottage in the heart of the village
14–21 May
Cottage in Somerset
4.94 out of 5 average rating, 209 reviewsCottage on River near Providence/Cape Cod/Newport
19–26 Nov
Family-friendly home rentals with a pool
Home in Sagamore Beach
4.91 out of 5 average rating, 146 reviewsSpacious Upper Cape Retreat with Private Pool
16–23 Mar
Home in Cotuit
4.91 out of 5 average rating, 11 reviewsShoestringBayHouse, waterfront & pool in Cotuit
4–11 Dec
Guest suite in Little Compton
4.93 out of 5 average rating, 89 reviewsBrimstone Hill Farm, Little Compton, RI
15–22 Sep
Home in Barnstable
4.94 out of 5 average rating, 99 reviewsPrivate Pool, near beaches, 3 BR/3 BA, Central Air
14–21 May
Condo in Tisbury
4.91 out of 5 average rating, 45 reviewsPrivate 3bdrm Condo Tashmoo Woods
1–8 Nov
Apartment in Hyannis
4.82 out of 5 average rating, 45 reviews1 bdrm 4ppl apartment,stairs,pool,no meals,deck
28 Jan – 4 Feb
Condo in Vineyard Haven
5.0 out of 5 average rating, 17 reviewsRelax....You're on Island Time......
30 Oct – 6 Nov
Home in Middletown
4.91 out of 5 average rating, 56 reviewsPOOL, July 6-13 open. Central Air. Walk to beach
12–19 Mar
Quick stats about holiday rentals that are family-friendly in Chilmark
Total rentals
160 properties
Wi-Fi availability
160 properties include access to Wi-Fi
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
$233 NZD before taxes and fees
Destinations to explore
- Cape Cod Holiday rentals
- Martha's Vineyard Holiday rentals
- Cambridge Holiday rentals
- Montauk Holiday rentals
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