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
16–23 Sep
Home in Oak Bluffs
4.93 out of 5 average rating, 169 reviewsSpectacular beach & pool combo; beautiful sunsets!
30 Jan – 6 Feb
Home in Centerville, Barnstable
4.97 out of 5 average rating, 141 reviewsLuxury House 0.25 mi from Craigville Beach
15–22 Feb
Flat in Oak Bluffs
4.92 out of 5 average rating, 128 reviewsVictorian Oasis: Driveway, hot tub, grill & more
28 Aug – 4 Sep
Home in Edgartown
4.99 out of 5 average rating, 68 reviewsContemporary 3BR/2.5 BA Edgartown Beauty
9–16 Feb
Home in Eastham
5.0 out of 5 average rating, 6 reviewsLovely villa w pool/hottub, central AC, near beach
27 Sep – 4 Oct
Home in Plymouth
4.85 out of 5 average rating, 67 reviewsAmazing ocean front 3 bedroom
17–24 May
Guest house in Oak Bluffs
4.99 out of 5 average rating, 73 reviewsMermaid Cottage
23–30 Dec
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
12–19 Jan
Home in Yarmouth Port, Cape Cod
4.99 out of 5 average rating, 312 reviewsFabulous Waterfront! 3bdrm/2bth Kayaks & Firepit
1–8 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
22–29 Mar
Home in Dennis
4.98 out of 5 average rating, 247 reviewsShirley's Place - Pet Friendly Sleeps Six!
22–29 Nov
Home in Brewster
4.98 out of 5 average rating, 168 reviewsSeaPeace Cottage-East Brewster Deck,Firepit,W/D AC
7–14 Sep
Home in Harwich
4.98 out of 5 average rating, 129 reviews* Game Room, Quiet St, NESN, Central AC, 4bd/2ba
19–26 Sep
Loft in Wellfleet
4.94 out of 5 average rating, 293 reviewsComfortable Studio Apartment
8–15 Dec
Home in Sandwich
4.93 out of 5 average rating, 194 reviewsCottage in the heart of the village
6–13 Jun
Family-friendly home rentals with a pool
Apartment in Provincetown
4.97 out of 5 average rating, 190 reviewsP-Town Beach Beauty on the Bay. Water View!
29 Mar – 5 Apr
Home in Plymouth
4.92 out of 5 average rating, 170 reviewsOur Secret Garden
12–19 Dec
Home in Sagamore Beach
4.91 out of 5 average rating, 146 reviewsSpacious Upper Cape Retreat with Private Pool
22–29 Nov
Home in Cotuit
4.91 out of 5 average rating, 11 reviewsShoestringBayHouse, waterfront & pool in Cotuit
4–11 Dec
Home in Plymouth
4.95 out of 5 average rating, 38 reviewsOur families slice of heaven
10–17 Oct
Guest house in Hyannis
4.86 out of 5 average rating, 44 reviews2 bdrm unit, stairs 4 nights min, pool, no meals
3–10 Dec
Home in Barnstable
4.94 out of 5 average rating, 99 reviewsPrivate Pool, near beaches, 3 BR/3 BA, Central Air
18–25 Oct
Apartment in North Truro
4.56 out of 5 average rating, 87 reviewsResort Style Studio Condominium W/Pool, Wifi & A/C
17–24 Sep
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
10T reviews
Nightly prices starting at
₹7,518 before taxes and fees
Destinations to explore
- Cape Cod Holiday rentals
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