Family-friendly vacation 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.

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Top guest favorite

The historic property is displayed from the street level, showcasing its architectural charm with a multi-story design. A covered porch is visible, featuring ornate woodwork. Shops line the street, contributing to a lively town atmosphere. Clear skies and bright sunlight enhance the inviting appearance.

Apartment in Oak Bluffs

4.92 out of 5 average rating, 109 reviews

Absolute Best Location on the Island

Ideal location for visitors in the middle of the most lively, diverse, fun town on Martha's Vineyard. This property is certified by the United States Department of Interior as a National Historic Property. The ferry terminal, restaurants, shops, markets, harbor, historic sites, entertainment, public transportation, and a clean sandy beach are all within minutes. A vehicle is not necessary. IF UNAVAILABLE: SIMILAR WALKABLE SISTER PROPERTY in Vineyard Haven: https://www.airbnb.com/rooms/49016488?

Guest favorite

A spacious living room is highlighted by a large grey sectional couch adorned with various throw pillows. A wooden coffee table sits in front, featuring storage compartments. Two abstract paintings in calming blues are displayed above the couch, while soft lighting illuminates the area.

Guest suite in Oak Bluffs

4.95 out of 5 average rating, 357 reviews

Lovely 2 BR Oak Bluffs Apartment

This 100% private apartment is on the first floor of a shared house where owners and their son live upstairs. There are no shared spaces. You have a private entrance and parking. The living room, bedrooms, bathroom, and kitchenette are bright and clean. It is exactly 1 mile from Oak Bluffs Center, a half mile from The Cottages and Farm Neck Golf Course, and a block from Tradewinds walking trails. Across the street is the bike path, & the bus stop is on the corner for easy island transportation!

Guest favorite

Home in Yarmouth

4.9 out of 5 average rating, 462 reviews

Beach House, Harbor View and Family Friendly.

Our house is a stones throw from the beach. The harbor, Hyannis, downtown, cafes, restaurants, anywhere from 5 star dining to family-friendly dining are all in walking distance. Several family friendly activities are very close. You’ll love our place because of the walk to the family friendly beach, the ambiance, the ocean view and the neighborhood feel. Our place is good for couples, solo adventurers, business travelers, fishermen, families (with kids) and large groups.

Superhost

The exterior of the home is presented at dusk, featuring soft outdoor lighting and classic blue siding. A pathway of stone leads to the entrance, flanked by neatly manicured shrubs and a lawn. A small porch area and steps provide access to the front door.

Home in Barnstable

4.88 out of 5 average rating, 133 reviews

The Mills Retreat- 3BR/2Bath - Beach pass included

-Spacious 3 bedroom / 2 bath home located on quiet cul-de-sac. -Large deck with patio set and grill on a private lot. -Barnstable Beach Pass included, valid at all Barnstable public beaches for 1 vehicle. -Central Air conditioning with 2 zones. -All TV's are Roku TV's in guest mode allowing you to use your own streaming apps. -Fast Wi-Fi for the whole family. -Large basement with TV which is great for kids. -Fully equipped kitchen -Full-size front loading washer & dryer.

Top guest favorite

A bright, airy hallway connects a dining area and a sunroom, featuring large windows that invite natural light. The dining room is furnished with a wooden table and chairs, while the sunroom showcases comfortable seating. Wood flooring adds warmth to the space.

Cottage in Barnstable

4.99 out of 5 average rating, 142 reviews

Beach Glass Cottage - Pond Front

Come stay at the Beach Glass Cottage! A pristine pond front, completely renovated and tastefully decorated, 3 bedroom, 2 bathroom cottage in the heart of Hyannis. Truly the perfect get-a-way for family and friends. The Beach Glass Cottage is tucked away from the action, but within walking distance to Main Street Hyannis, which features eclectic shops, restaurants, bars, ice cream with mini golf and the Cape Cod Melody Tent is a short walk from the cottage as well.

Guest favorite

The open living area features a comfortable seating arrangement with a sofa and armchairs, arranged around a coffee table. A large TV is mounted on the wall, while natural light fills the space through windows with light curtains. The kitchen area is visible in the background.

Cottage in Hyannis

4.92 out of 5 average rating, 119 reviews

Beautifully Updated, Classic Cape in Hyannisport

NEWLY RENOVATED KITCHEN & LIVING ROOM Within 1/2 mile to the beach, historic Hyannisport, downtown Hyannis Main Street, restaurants, Melody Tent and nightlife. -New mattresses on beds. Private setting. Very quiet neighborhood. Includes Beach Parking Pass -($25 daily) for all Barnstable Beaches. Great for families & groups over the age of 25. * Sheets, towels, beach chairs, and much, much more * No parties, excessive noise , pets, or smoking permitted.

Superhost

A modern kitchen is showcased, featuring dark cabinetry and granite countertops. Stainless steel appliances, including a microwave and dishwasher, are visible. A mosaic backsplash adds visual interest, while a brightly colored kettle sits atop the stove. An open doorway leads to a well-lit bathroom with framed mirrors.

Cottage in Oak Bluffs

4.9 out of 5 average rating, 198 reviews

Beautiful stroll to beach and all of downtown!

Walk to all Oak Bluffs has to offer. 5-10 Min. walk to the Harbor, Town and Inkwell Beach. Amazing location! This property is 2 minutes walk from the Gingerbread cottages. Outside there is a private patio, outdoor shower and Gas grill. Inside there is two smart Tv, Wifi, Tile floors, Marble shower, Laundry and all turn key including linens. The added bonus is this unit is brand new construction complete with new furniture and a stocked full size kitchen.

Superhost

A spacious two-story house features a wrap-around farmers porch with comfortable seating, nestled among lush green grass. The architectural style reflects a classic Cape Cod design, while large windows allow for ample natural light, connecting the indoor and outdoor areas.

Home in Oak Bluffs

4.81 out of 5 average rating, 108 reviews

Beautiful 3 bedroom in Oak Bluffs, walk to beach

Located in Martha's Vineyard, close to beach, bike path, oak bluffs center, art and culture, parks,and the airport. You’ll love my place because of the outdoors space with a wrap around farmers porch, the proximity to the ferry, walking distance to neighborhood beach, less than 2 miles from ferry, screened in porch, central a/c, hardwood floors and an open floor plan. Real Cape Cod feel with modern amenities. Most of my guest come back year after year!

Top guest favorite

The exterior of a charming two-story cottage is visible, featuring light grey shingles and blue-striped awnings. A well-maintained lawn with colorful flowers and greenery surrounds the house, while a gravel path leads to the entrance. Sunlight casts a warm glow over the scene.

Cottage in Yarmouth

4.94 out of 5 average rating, 108 reviews

Cape Cod charmer 5 minute walk to Ocean beaches

Your oasis to relax, quite street, private back yard with large deck, gas grill, outdoor shower, breezeway and front deck. About a 5 minute walk to two ocean beaches on Nantucket Sound. Enjoy your morning coffee on a park bench as the sun rises over the ocean. Walking distance via sidewalk to beaches, seafood restaurant, Bass River beach pier and Joshua Baker windmill. Saturday to Saturday weekly rentals from late June to early Sept.

Top guest favorite

Cottage in Yarmouth

4.84 out of 5 average rating, 237 reviews

Charming Cottage near Beach and Ferry.

2022 renovation (floors, bathroom, cabinets) The cottage is only 150 yards from a sandy residential beach. Good for couples, families (with kids), and furry friends (pets). Enjoy a great outdoor shower, grill and deck, wifi, central AC/heat, cable TV, linens, washer/dryer. Additional Beach gear. No host interaction required. Great place to work remotely. Private yard and picnic table with lots of takeout options nearby.

Top guest favorite

Home in Falmouth

4.94 out of 5 average rating, 308 reviews

Absolutely Adorable 4 Bedroom Ranch

Property is very close to beach at lovely, freshwater Jenkins Pond. This nicely furnished rental has a fabulous lower level family/TV room with add'l sleeping area and a full bath. Outdoors there is a large yard with a large deck and outside shower during the summer season. Minimum 2-night stay, rates may vary depending on season, weekly and monthly rate available.

Guest favorite

A bright living space is shown with large sliding doors offering views of the water. Natural light fills the room, highlighting a comfortable sectional sofa, a cozy ottoman, and a decorative armchair. Stylish decor elements create a welcoming environment, perfect for relaxation.

Home in Mashpee

4.96 out of 5 average rating, 184 reviews

Gorgeous sunsets! Private family beach - Cape Cod!

Saturday to Saturday weekly rental during summer months. Wrap around deck, beach and waterfront. Open layout. Perfect for families & Couples with a family beach . Stunning sunsets, very private and close to Mashpee commons, Falmouth and New Seabury all 10 minutes away. We are happy to have you for stays longer than 7 days! Just send us a note!