Family-friendly vacation rentals in Chappaquiddick Island
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Top-rated family-friendly rentals in Chappaquiddick Island
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation 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
Feb 16 – 23
Home in Centerville, Barnstable
4.97 out of 5 average rating, 142 reviewsLuxury House 0.25 mi from Craigville Beach
Mar 17 – 24
Home in Edgartown
4.99 out of 5 average rating, 68 reviewsContemporary Edgartown Beauty: The Perfect Retreat
Feb 13 – 20
Home in Edgartown
5.0 out of 5 average rating, 47 reviewsOn HGTV! Gorgeous, AC, Hot Tub, WALK Town & Beach
Oct 25 – Nov 1
Guesthouse in Oak Bluffs
4.99 out of 5 average rating, 73 reviewsMermaid Cottage
Feb 23 – Mar 2
Home in Falmouth
4.89 out of 5 average rating, 57 reviewsPeaceful waterfront home with dock/ hot tub
Apr 26 – May 3
Home in Dennis
4.91 out of 5 average rating, 43 reviewsCape Cod Lakefront Home
Jun 8 – 15
Condo in Brewster
4.95 out of 5 average rating, 19 reviewsEscape to the Cape
Nov 10 – 17
Family- and pet-friendly home rentals
Guesthouse in Tisbury
4.86 out of 5 average rating, 227 reviewsAdorable Vineyard Haven Cottage
Oct 10 – 17
Cottage in Sandwich
4.87 out of 5 average rating, 307 reviewsOceanfront Cottage w/Private Beach ~ Lil’ Sea Sass
Jan 16 – 23
Cottage in Tisbury
4.96 out of 5 average rating, 216 reviewsNot Your Great Aunt's Island Cottage
Dec 8 – 15
Home in Yarmouth Port, Cape Cod
4.99 out of 5 average rating, 312 reviewsFabulous Waterfront! 3bdrm/2bth Kayaks & Firepit
Dec 21 – 28
Guesthouse in Sagamore Beach
4.99 out of 5 average rating, 300 reviewsThe Guest House
Dec 17 – 24
Home in Sandwich
4.93 out of 5 average rating, 195 reviewsCottage in the heart of the village
May 14 – 21
Tiny home in Dennis Port
4.81 out of 5 average rating, 439 reviews★TINY HOUSE★4/10mi Beach & Village★Pet OK★2 Bikes
Feb 9 – 16
Home in Oak Bluffs
4.77 out of 5 average rating, 104 reviewsCozy Vacation Getaway On Bike Path
Jan 8 – 15
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
Mar 16 – 23
Home in Cotuit
4.91 out of 5 average rating, 11 reviewsShoestringBayHouse, waterfront & pool in Cotuit
Dec 4 – 11
Home in Barnstable
4.94 out of 5 average rating, 99 reviewsPrivate Pool, near beaches, 3 BR/3 BA, Central Air
May 14 – 21
Apartment in Hyannis
4.82 out of 5 average rating, 45 reviews1 bdrm 4ppl apartment,stairs,pool,no meals,deck
Jan 28 – Feb 4
Condo in Vineyard Haven
5.0 out of 5 average rating, 17 reviewsRelax....You're on Island Time......
Oct 30 – Nov 6
Condo in Tisbury
4.91 out of 5 average rating, 45 reviewsPrivate 3bdrm Condo Tashmoo Woods
Nov 1 – 8
Home in Falmouth
4.93 out of 5 average rating, 15 reviewsGorgeous Cape Cod Property!
Feb 16 – 23
Apartment in Falmouth
4.81 out of 5 average rating, 128 reviewsQuaint North Falmouth near Old Silver Beach
Jun 4 – 11
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