
Family-friendly holiday rentals in Chappaquiddick
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Chappaquiddick
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Lovely 2 BR Oak Bluffs Apartment
*To returning guests: Airbnb has restructured their fees; so while our nightly price may look higher at first glance, it is our same pricing overall This private apartment is on the 1st floor of a family home with a personal entrance & parking; owners and their son live upstairs. There are no shared spaces. It is a mile from Oak Bluffs Center, a half mile from the Cottages and Farm Neck Golf Course, and across the street is a bike path. The bus stop is on the corner for easy island wide travel!
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Walk to EDG Wharf - Outdoor Shower, AC, and Grill
Just a short walk to Edgartown's shops & restaurants, this cape style home features open concept living, stainless steel appliances, bamboo floors, oversize 2 car garage, washer/dryer and outdoor shower! The master suite includes a sitting area, walk in closet & attached bath with walk-in shower, soaking tub & double vanity. Additional 3 BRs include queen/twin beds & 2 full baths. Kitchen sliders lead to outdoor brick patio with BBQ and dining area. Outdoors games and four bikes included.
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Perfect for couples, 10 min walk to Edg, big patio
* Private garden patio: string lights create chill evenings around the propane fire pit. Table & chairs, propane grill, & enclosed outdoor shower * 10 min walk to Edgartown's dining & boutiques * Cable TV, Streaming services, Sonos * High-speed WiFi, comfortable workspace in the bedroom * USB charging ports in the BR & LR * Small but mighty fully stocked kitchen for home-cooked meals * Organic, local bath products * Board games & a small library * HW floors, SS Bosch appliances, DW, W/D, HVAC
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Arrowsmith Cottage-Oak Bluffs Near Eastville Beach
Welcome to Arrowsmith Cottage! If you are considering bringing your small dog, please first contact me (scroll down on the cottage's listing page and click on the "Contact Host" button), and tell me a little bit about him/her, as dogs require homeowner's written approval and guest’s agreement to the pet fee and homeowners’ pet rules. We cannot allow cats, birds, or any animals other than one pre-approved dog. Hosts are not responsible for listing inaccuracies due to Airbnb's own input or AI.
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Chappy cottage close to ferry & walk to beach
Booking for '26 Season. Charming cottage is a 5-minute bike ride to the Chappy ferry & beach and a 10-15 minute walk to the Frances Preserve beach. Located in a quiet wooded setting, the property offers new furniture and beds; renovated kitchen with dishwasher and microwave; new bath w/ shower/tub; washer/dryer; hardwood; screen porch; deck & outdoor shower. Cable, wifi (200 megs), AC, ceiling fan, grill, deck furniture, beach chairs & umbrella. The rental season runs mid May through late Oct.
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Chappy Beach House *DERBY DATES!*
Welcome to this charming 4-bedroom retreat tucked just off Chappaquiddick’s only paved road. Perfectly situated minutes from the Chappy Ferry, downtown Edgartown, and some of the island’s most pristine, uncrowded beaches. Features include AC, high-speed WiFi, a washer/dryer, and a gas grill for laid-back summer dinners. Whether you’re a longtime Vineyard lover or discovering Chappy for the first time, this home offers the ideal base to experience the island’s quiet beauty and classic charm.
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East Chop Cottage - walk to lighthouse & beach!
This quaint little cottage is located in the heart of East Chop, a neighborhood of Oak Bluffs. East Chop features the high, prominent bluffs that gave Oak Bluffs its name. A lighthouse, East Chop Light, stands at the north end of the chop on Telegraph Hill- only a five minute walk from the cottage. The cottage is a twelve minute walk to the harbor, and about a mile from the Oak Bluffs ferry! There is a public beach about 1/2 mile down the road. ***This space is not suitable for children
Indoor spacesFamilyAccess

Private Pond-side Cape Cod Home
Charming 2 bedroom home located on Flax Pond. Enjoy a private sandy beach and dock. Swim, kayak, fish, boat (trolling motors only) and just relax. Enjoy the home’s spacious deck with comfortable seating for the whole family complete with chiminea for late night fires. 2 levels of lodging with central air. 2 full bathrooms, kitchen, dining room and great room. Minutes away from town beaches, bike path, golf, and shopping. Parking for approximately 4 cars.
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The Luxury Vineyard Yurt
Discover this exceptional Luxury Yurt firsthand! Upon entering, you will be welcomed by a distinctive experience, featuring textured concrete radiant floors and a four-foot circular central skylight. Every aspect has been meticulously designed, allowing you to relax in a generous private yard. Enjoy your evenings under the stars, utilize the complimentary paddling, practice yoga in the spacious loft, and indulge in the beauty of your private island Yurt!
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Beachfront Cottage w. Yard + Town Access
Welcome to The Mizzen Cottage! Updated 1930's cottage on an ocean front compound on beautiful Chappaquiddick. Complete with a picturesque porch overlooking the outer harbor, side deck, outdoor shower, washer/dryer, dishwasher. Stunning views of the Edgartown lighthouse and Cape Poge. Access to a private beach. Access town with just a 10 minute walk (or 1 minute drive) to the Chappaquiddick Ferry, and be in downtown Edgartown in 15 minutes or less!
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Seacoast Shores Oasis-Steps From Private Beach Bay
Our 2,400 square feet family-friendly house located on the East Falmouth Seacoast shores awaits your arrival! It is located steps away from the private lush beach bay. Newly remodeled and furnished with an excellent yard space for grilling, relaxation, and games suitable for all ages! Our house features an outdoor hot tub, outdoor kitchen, grill, koi pond, fire pit, outdoor shower, spacious modern kitchen, and kayak ready for your enjoyment.
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Quiet Hide Away
Lovely efficiency suite with private entrance in a quiet neighborhood. Private space located over attached garage. Plenty of space for two guests. Comfortably appointed with queen bed, dining set, living area with tv and full bath. Enjoy a coffee or cocktail on the private deck. Toaster oven, refrigerator and coffee maker will start your day right before heading to nearby beaches, golf courses or shopping.
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Popular amenities for Chappaquiddick family-friendly rentals
Family-friendly home rentals with a hot tub

Oak bluffs cottage Perfect place to honeymoon!
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Luxury House 0.25 mi from Craigville Beach
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Quiet West Tisbury 2 BDR Suite
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Waterfront•Hot Tub • Kayaks/SUP's • King Bed •Dock
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Vineyard Vacation, 3-Bedroom, Hot-tub, Golf course
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On HGTV! Gorgeous, AC, Hot Tub, WALK Town & Beach
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Valentine's Retreat Hot Tub Fire Pit Trails Beach
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Vineyard Meadow Writer's Cottage with Hot Tub
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Family- and pet-friendly home rentals

Katama Barn
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impeccable cottage STEPS to downtown OB & beach!
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Lambert's Cove Oceanview Beach Pass Trails nearby
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Cape Cod Cotuit Cottage, 3 Bed Near Beaches
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Mid-Century Modern home 5 minute walk to beach
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Lambert's Cove, Water view, Beach pass
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Waterview, Private, Walk to Beach, Mile to Town
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Charming water-front cottage on Martha's Vineyard!
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Family-friendly home rentals with a pool

New Seabury Cape Condo | Pool & Beach Escape
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“The Hideaway”Private Guest Suite/Pool/Beach Pass
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Private Pool, near beaches, 3 BR/3 BA, Central Air
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The Holly Cottage
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Quaint North Falmouth near Old Silver Beach
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Cozy downtown apartment
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Beautiful Edgartown 3500 sq ft home, heated pool
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Coastal Charm New Seabury: 5BRs with Private Pool
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Destinations to explore
- Cape Cod
- Mayflower Beach
- West Dennis Beach
- Craigville Beach
- Onset Beach
- Bonnet Shores Beach
- East Sandwich Beach
- Duxbury Beach
- Sandy Neck Beach
- Saquish Beach
- Easton Beach
- Nauset Beach
- New Silver Beach
- Skaket Beach
- Popponesset Peninsula
- Cape Cod Canal
- Falmouth Heights Beach
- Pinehills Golf Club
- Inkwell Beach
- The Breakers
- Second Beach
- Coast Guard Beach
- Cape Cod Inflatable Park
- Easton's Beach





