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 β 2 Feb
Home in Oak Bluffs
4.93 out of 5 average rating, 169 reviewsSpectacular beach & pool combo; beautiful sunsets!
8β15 Mar
Home in Centerville, Barnstable
4.97 out of 5 average rating, 141 reviewsLuxury House 0.25 mi from Craigville Beach
27 Feb β 6 Mar
Flat in Oak Bluffs
4.92 out of 5 average rating, 128 reviewsVictorian Oasis: Driveway, hot tub, grill & more
6β13 Mar
Guest house in Oak Bluffs
4.99 out of 5 average rating, 73 reviewsMermaid Cottage
4β11 Apr
Home in Plymouth
4.85 out of 5 average rating, 67 reviewsAmazing ocean front 3 bedroom
4β11 Mar
Home in Edgartown
4.99 out of 5 average rating, 68 reviewsContemporary 3BR/2.5 BA Edgartown Beauty
6β13 Feb
Home in Eastham
5.0 out of 5 average rating, 6 reviewsLovely villa w pool/hottub, central AC, near beach
27 Sep β 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
14β21 Jan
Tiny home in Dennis Port
4.81 out of 5 average rating, 436 reviewsβ TINY HOUSEβ 4/10mi Beach & Villageβ Pet OKβ 2 Bikes
1β8 Mar
Home in Yarmouth Port, Cape Cod
4.99 out of 5 average rating, 312 reviewsFabulous Waterfront! 3bdrm/2bth Kayaks & Firepit
18β25 Nov
Home in Harwich
4.98 out of 5 average rating, 129 reviews* Game Room, Quiet St, NESN, Cent AC/ Heat 4bd/2ba
19β26 Sep
Home in Brewster
4.98 out of 5 average rating, 168 reviewsSeaPeace Cottage-East Brewster Deck,Firepit,W/D AC
30 Sep β 7 Oct
Cottage in Sandwich
4.88 out of 5 average rating, 305 reviewsOceanfront Cottage w/Private Beach ~ Lilβ Sea Sass
13β20 Apr
Home in Dennis
4.98 out of 5 average rating, 247 reviewsShirley's Place - Pet Friendly Sleeps Six!
5β12 May
Loft in Wellfleet
4.93 out of 5 average rating, 292 reviewsComfortable Studio Apartment
5β12 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!
2β9 Dec
Home in Plymouth
4.92 out of 5 average rating, 170 reviewsOur Secret Garden
2β9 Nov
Home in Cotuit
4.91 out of 5 average rating, 11 reviewsShoestringBayHouse, waterfront & pool in Cotuit
19β26 Dec
Home in Plymouth
4.95 out of 5 average rating, 38 reviewsOur families slice of heaven
7β14 Oct
Guest house in Hyannis
4.86 out of 5 average rating, 44 reviews2 bdrm unit, stairs 4 nights min, pool, no meals
13β20 Dec
Home in Barnstable
4.94 out of 5 average rating, 99 reviewsPrivate Pool, near beaches, 3 BR/3 BA, Central Air
4β11 Jun
Apartment in North Truro
4.56 out of 5 average rating, 87 reviewsResort Style Studio Condominium W/Pool, Wifi & A/C
28 Oct β 4 Nov
Flat in Yarmouth
4.73 out of 5 average rating, 33 reviewsOn Smuggler's Beach Cape Cod
18β25 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
β¬Β 84 before taxes and fees
Destinations to explore
- Cape CodΒ Holiday rentals
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- Family-friendly rentalsΒ United States
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