Family-friendly holiday rentals in Chappaquiddick Island
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Chappaquiddick Island
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 Chappaquiddick Island 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
Home in Centerville, Barnstable
4.97 out of 5 average rating, 142 reviewsLuxury House 0.25 mi from Craigville Beach
17–24 Mar
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
Guest house 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
Apartment in Brewster
4.95 out of 5 average rating, 19 reviewsEscape to the Cape
10–17 Nov
Family- and pet-friendly home rentals
Guest house 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
Cottage in Tisbury
4.96 out of 5 average rating, 216 reviewsNot Your Great Aunt's Island Cottage
8–15 Dec
Home in Yarmouth Port, Cape Cod
4.99 out of 5 average rating, 312 reviewsFabulous Waterfront! 3bdrm/2bth Kayaks & Firepit
21–28 Dec
Guest house in Sagamore Beach
4.99 out of 5 average rating, 300 reviewsThe Guest House
17–24 Dec
Home in Sandwich
4.93 out of 5 average rating, 195 reviewsCottage in the heart of the village
14–21 May
Tiny home in Dennis Port
4.81 out of 5 average rating, 439 reviews★TINY HOUSE★4/10mi Beach & Village★Pet OK★2 Bikes
9–16 Feb
Home in Oak Bluffs
4.77 out of 5 average rating, 104 reviewsCozy Vacation Getaway On Bike Path
8–15 Jan
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
Home in Barnstable
4.94 out of 5 average rating, 99 reviewsPrivate Pool, near beaches, 3 BR/3 BA, Central Air
14–21 May
Flat in Hyannis
4.82 out of 5 average rating, 45 reviews1 bdrm 4ppl apartment,stairs,pool,no meals,deck
28 Jan – 4 Feb
Apartment in Vineyard Haven
5.0 out of 5 average rating, 17 reviewsRelax....You're on Island Time......
30 Oct – 6 Nov
Apartment in Tisbury
4.91 out of 5 average rating, 45 reviewsPrivate 3bdrm Condo Tashmoo Woods
1–8 Nov
Home in Falmouth
4.93 out of 5 average rating, 15 reviewsGorgeous Cape Cod Property!
16–23 Feb
Flat in Falmouth
4.81 out of 5 average rating, 128 reviewsQuaint North Falmouth near Old Silver Beach
4–11 Jun
Destinations to explore
- Cape Cod Holiday rentals
- Martha's Vineyard Holiday rentals
- Cambridge Holiday rentals
- Montauk Holiday rentals
- Nantucket Holiday rentals
- Salem Holiday rentals
- Newport Holiday rentals
- Philadelphia Holiday rentals
- New York Holiday rentals
- Jersey City Holiday rentals
- The Hamptons Holiday rentals
- Boston Holiday rentals
- Family-friendly rentals United States
- Family-friendly rentals Boston
- Family-friendly rentals Cape Cod
- Family-friendly rentals Martha's Vineyard
- Family-friendly rentals Massachusetts
- House rentals Chappaquiddick Island
- Rentals with a patio Chappaquiddick Island
- Rentals with a washing machine and dryer Chappaquiddick Island
- Monthly Rentals Chappaquiddick Island
- Rentals with beach access Chappaquiddick Island
- Family-friendly rentals Edgartown
- Family-friendly rentals Dukes County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom