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. 27 – Mar. 6
Home in Centerville, Barnstable
4.97 out of 5 average rating, 141 reviewsLuxury House 0.25 mi from Craigville Beach
Apr. 28 – May 5
Home in Edgartown
4.99 out of 5 average rating, 68 reviewsContemporary Edgartown Beauty: The Perfect Retreat
Feb. 15 – 22
Home in Edgartown
5.0 out of 5 average rating, 47 reviewsOn HGTV! Gorgeous, AC, Hot Tub, WALK Town & Beach
Sep. 29 – Oct. 6
Guesthouse in Oak Bluffs
4.99 out of 5 average rating, 73 reviewsMermaid Cottage
Mar. 1 – 8
Home in Falmouth
4.89 out of 5 average rating, 57 reviewsPeaceful waterfront home with dock/ hot tub
Apr. 25 – May 2
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
Apr. 18 – 25
Family- and pet-friendly home rentals
Guesthouse in Tisbury
4.86 out of 5 average rating, 227 reviewsAdorable Vineyard Haven Cottage
Oct. 7 – 14
Home in Tisbury
4.98 out of 5 average rating, 248 reviewsSunny, Spacious Vineyard Retreat
Sep. 14 – 21
Cottage in Tisbury
4.96 out of 5 average rating, 216 reviewsNot Your Great Aunt's Island Cottage
Nov. 23 – 30
Cottage in Sandwich
4.87 out of 5 average rating, 307 reviewsOceanfront Cottage w/Private Beach ~ Lil’ Sea Sass
Jan. 18 – 25
Home in Sandwich
4.93 out of 5 average rating, 194 reviewsCottage in the heart of the village
May 14 – 21
Tiny homes in Dennis Port
4.81 out of 5 average rating, 438 reviews★TINY HOUSE★4/10mi Beach & Village★Pet OK★2 Bikes
Nov. 21 – 28
Guesthouse in Sagamore Beach
4.99 out of 5 average rating, 300 reviewsThe Guest House
Feb. 7 – 14
Home in Yarmouth Port, Cape Cod
4.99 out of 5 average rating, 312 reviewsFabulous Waterfront! 3bdrm/2bth Kayaks & Firepit
Aug. 23 – 30
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
Apr. 2 – 9
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
Apr. 10 – 17
Apartment in Hyannis
4.82 out of 5 average rating, 45 reviews1 bdrm 4ppl apartment,stairs,pool,no meals,deck
Mar. 12 – 19
Condo in Vineyard Haven
5.0 out of 5 average rating, 17 reviewsRelax....You're on Island Time......
Sep. 18 – 25
Condo in Tisbury
4.91 out of 5 average rating, 45 reviewsPrivate 3bdrm Condo Tashmoo Woods
Oct. 8 – 15
Home in Falmouth
4.93 out of 5 average rating, 15 reviewsGorgeous Cape Cod Property!
Feb. 14 – 21
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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