Family-friendly holiday rentals 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
26 Jan – 2 Feb
Home in Oak Bluffs
4.93 out of 5 average rating, 169 reviewsSpectacular beach & pool combo; beautiful sunsets!
8–15 Mar
Home in Centerville, Barnstable
4.97 out of 5 average rating, 141 reviewsLuxury House 0.25 mi from Craigville Beach
27 Feb – 6 Mar
Flat in Oak Bluffs
4.92 out of 5 average rating, 128 reviewsVictorian Oasis: Driveway, hot tub, grill & more
6–13 Mar
Guest house in Oak Bluffs
4.99 out of 5 average rating, 73 reviewsMermaid Cottage
4–11 Apr
Home in Plymouth
4.85 out of 5 average rating, 67 reviewsAmazing ocean front 3 bedroom
4–11 Mar
Home in Edgartown
4.99 out of 5 average rating, 68 reviewsContemporary 3BR/2.5 BA Edgartown Beauty
6–13 Feb
Home in Eastham
5.0 out of 5 average rating, 6 reviewsLovely villa w pool/hottub, central AC, near beach
27 Sept – 4 Oct
Family- and pet-friendly home rentals
Guest house in Plymouth
4.79 out of 5 average rating, 184 reviewsA peaceful retreat on Cape Cod Bay
14–21 Jan
Tiny home in Dennis Port
4.81 out of 5 average rating, 437 reviews★TINY HOUSE★4/10mi Beach & Village★Pet OK★2 Bikes
1–8 Mar
Home in Yarmouth Port, Cape Cod
4.99 out of 5 average rating, 312 reviewsFabulous Waterfront! 3bdrm/2bth Kayaks & Firepit
18–25 Nov
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
30 Sept – 7 Oct
Cottage in Sandwich
4.88 out of 5 average rating, 305 reviewsOceanfront Cottage w/Private Beach ~ Lil’ Sea Sass
13–20 Apr
Home in Dennis
4.98 out of 5 average rating, 247 reviewsShirley's Place - Pet Friendly Sleeps Six!
5–12 May
Loft in Wellfleet
4.93 out of 5 average rating, 292 reviewsComfortable Studio Apartment
5–12 Dec
Family-friendly home rentals with a pool
Apartment in Provincetown
4.97 out of 5 average rating, 189 reviewsP-Town Beach Beauty on the Bay. Water View!
2–9 Dec
Home in Plymouth
4.92 out of 5 average rating, 170 reviewsOur Secret Garden
2–9 Nov
Home in Cotuit
4.91 out of 5 average rating, 11 reviewsShoestringBayHouse, waterfront & pool in Cotuit
19–26 Dec
Home in Plymouth
4.95 out of 5 average rating, 38 reviewsOur families slice of heaven
7–14 Oct
Guest house in Hyannis
4.86 out of 5 average rating, 44 reviews2 bdrm unit, stairs 4 nights min, pool, no meals
13–20 Dec
Home in Barnstable
4.94 out of 5 average rating, 99 reviewsPrivate Pool, near beaches, 3 BR/3 BA, Central Air
4–11 Jun
Apartment in North Truro
4.56 out of 5 average rating, 87 reviewsResort Style Studio Condominium W/Pool, Wifi & A/C
28 Oct – 4 Nov
Flat in Yarmouth
4.73 out of 5 average rating, 33 reviewsOn Smuggler's Beach Cape Cod
18–25 Feb
Quick stats about 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
£72 before taxes and fees
Destinations to explore
- Cape Cod Holiday rentals
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