Family-friendly holiday houses in Chatham
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Chatham
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 Chatham family-friendly rentals
Family-friendly home rentals with a hot tub
Home in Dennis
4.79 out of 5 average rating, 139 reviewsWalk2Beach, HotTub, FirePit, PetsOk
9 – 16 Oct
Home in Oak Bluffs
4.93 out of 5 average rating, 169 reviewsSpectacular beach & pool combo; beautiful sunsets!
13 – 20 Jan
Home in Centerville, Barnstable
4.97 out of 5 average rating, 141 reviewsLuxury House 0.25 mi from Craigville Beach
10 – 17 Nov
Apartment in Oak Bluffs
4.92 out of 5 average rating, 128 reviewsVictorian Oasis: Driveway, hot tub, grill & more
27 Aug – 3 Sept
Home in Eastham
5.0 out of 5 average rating, 6 reviewsLovely villa w pool/hottub, central AC, near beach
27 Sept – 4 Oct
Home in Edgartown
4.99 out of 5 average rating, 68 reviewsContemporary 3BR/2.5 BA Edgartown Beauty
8 – 15 Feb
Home in Plymouth
4.85 out of 5 average rating, 67 reviewsAmazing ocean front 3 bedroom
6 – 13 Mar
Guesthouse in Oak Bluffs
4.99 out of 5 average rating, 73 reviewsMermaid Cottage
31 Mar – 7 Apr
Family- and pet-friendly home rentals
Guesthouse in Plymouth
4.79 out of 5 average rating, 184 reviewsA peaceful retreat on Cape Cod Bay
15 – 22 Apr
Home in Yarmouth Port, Cape Cod
4.99 out of 5 average rating, 312 reviewsFabulous Waterfront! 3bdrm/2bth Kayaks & Firepit
25 Jan – 1 Feb
Tiny home in Dennis Port
4.81 out of 5 average rating, 437 reviews★TINY HOUSE★4/10mi Beach & Village★Pet OK★2 Bikes
14 – 21 Oct
Home in Truro
4.88 out of 5 average rating, 172 reviewsCape Cod Getaway 2 Bedroom Cozy Home
29 Oct – 5 Nov
Home in Dennis
4.98 out of 5 average rating, 247 reviewsShirley's Place - Pet Friendly Sleeps Six!
6 – 13 Dec
Home in Harwich
4.98 out of 5 average rating, 129 reviews* Game Room, Quiet St, NESN, Central AC, 4bd/2ba
19 – 26 Sept
Home in Brewster
4.98 out of 5 average rating, 168 reviewsSeaPeace Cottage-East Brewster Deck,Firepit,W/D AC
2 – 9 Oct
Loft in Wellfleet
4.94 out of 5 average rating, 293 reviewsComfortable Studio Apartment
7 – 14 Dec
Family-friendly home rentals with a pool
Condo in Provincetown
4.97 out of 5 average rating, 189 reviewsP-Town Beach Beauty on the Bay. Water View!
1 – 8 Oct
Home in Plymouth
4.92 out of 5 average rating, 170 reviewsOur Secret Garden
14 – 21 Nov
Home in Sagamore Beach
4.91 out of 5 average rating, 146 reviewsSpacious Upper Cape Retreat with Private Pool
15 – 22 Nov
Home in Cotuit
4.91 out of 5 average rating, 11 reviewsShoestringBayHouse, waterfront & pool in Cotuit
19 – 26 Dec
Apartment in Hyannis
4.82 out of 5 average rating, 45 reviews1 bdrm 4ppl apartment,stairs,pool,no meals,deck
3 – 10 Mar
Home in Plymouth
4.95 out of 5 average rating, 38 reviewsOur families slice of heaven
7 – 14 Feb
Home in Barnstable
4.94 out of 5 average rating, 99 reviewsPrivate Pool, near beaches, 3 BR/3 BA, Central Air
16 – 23 Oct
Condo in North Truro
4.56 out of 5 average rating, 87 reviewsResort Style Studio Condominium W/Pool, Wifi & A/C
17 – 24 Sept
Quick stats about accommodation & holiday rentals that are family-friendly in Chatham
Total rentals
450 properties
Rentals with dedicated workspaces
180 properties have a dedicated workspace
Rentals with a pool
20 properties have a pool
Pet-friendly rentals
150 properties allow pets
Total number of reviews
10K reviews
Nightly prices starting at
$137 AUD before taxes and fees
Destinations to explore
- Cape Cod Accommodation & holiday rentals
- Martha's Vineyard Holiday rentals
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