
Family-friendly holiday rentals in Chappaquiddick
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Top-rated family-friendly rentals in Chappaquiddick
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Step Away; A Martha's Vineyard Retreat
Studio apartment addition attached to our family home. Our home is located three miles to downtown Edgartown with bus service & bike path close by. Private entrance, mini fridge, coffee press & accessories, private bath with shower, washer/dryer, bed in a loft area (ladder access only) with queen size sofa bed available below for additional sleeping. This is our family home with two baby boys. We try our best to keep quiet, but it is important to note their presence; rental has a sound machine.

Lambert's Cove, Water view, Beach pass, Ferry Tix
Enjoy stunning views of Vineyard Sound from this cozy three bedroom two bath home in a quiet neighborhood just minutes from Lambert's Cove Beach. This upside down house has one bedroom on the main level along with a full bath and open kitchen, dining, and family room. The downstairs has another living space, two bedrooms, laundry room, and full bath. Enjoy family time in the open upstairs with water views, or retreat to the lower level living room for some separation, quiet time, or work space.

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.

Sunny Studio Apartment on Martha's Vineyard
Our Sunny Studio is centrally located on Martha's Vineyard. A down-island location with an up-island feel. Open and airy studio with kitchenette and bath. The apartment has all the essentials. The apartment is located within walking distance of hiking and biking trails. A 10 to 15 minute car ride to any down-island town / beach. ***Please Note: Although conveniently located we are not within walking distance to Bars or Restaurants. We do recommend first time visitors rent or bring a car.

Saunaꕥ King Bedsꕥ Shed Barꕥ Firepitꕥ Fenced Yard
Cape Away is a cozy, family and pet-friendly Mid-Cape retreat with a private sauna, outdoor shower, fire pit, and fenced backyard. Start your day with a Nespresso in the fully stocked kitchen, explore nearby beaches, then unwind by the fire or in the sauna. With games, shed bar, fast WiFi, and free premium streaming on all smart TVs, you’re just 5–10 minutes from top restaurants and beaches. ꕥ Zero linen, towel or pet fees ꕥ Traveling on a budget? Send an inquiry, we’re happy to chat.

Lambert's Cove Oceanview FERRY Tikts See descript
Car FERRY TKTS avail. for purchase for weeks 7/4/26, 7/11/26, and 7/18/26. Salt box home set in the forested hills above Lambert's Cove. Short walk / drive to town beach. Perfect for family gatherings, home has 3 bedrooms , loft for virtual work space or reading room, 1.5 baths plus the fully enclosed outdoor shower, fully stocked kitchen, a deck that has seating for relaxing and also an octagonal picnic table, as well as lots of yard space for children or pups to play.

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.

Juniper Point Cottage With Ocean View
Charming Cape Cod cottage on semi-private road with and ocean view of Vineyard Sound. Renovations completed in mid-July, 2020. Three BR, 2 private attached baths, 1 semi-private bath, fully equipped kitchen, patio with BBQ grill, gas fireplace, cable-TV, WiFi internet, large second-floor deck, a/c.. Close to Vineyard Ferry, bus station and town. Seasonal rent. Please complete a reservation request to determine the rent in effect for your requested dates.

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!

Stylish Getaway|Outdoor Shower|Patio|walk to town
* Private garden patio: table & chairs, propane grill, propane fire pit & 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

Close to Edgartown Village Center!
This 1800 square foot Ranch-style Condo with loft was built in 2018 and is set on a large nicely landscaped lot with plenty of room inside and out. It has 3 bedrooms and a loft and sleeps 9. It’s a 20-minute walk to the Edgartown village center, a 10-minute walk to Morning Glory Farm, and just a 10-minute drive to South Beach! All updated furnishings, beds, linens, appliances. Read our reviews! Immaculate!

Katama Barn
Selected dog friendly, Immaculate beach house this is the perfect property to bike to the beach and then to dinner in Edgartown. 1.2 miles from beach South Beach, and 1 mile from Edgartown's Main Street. Outdoor shower, large private yard.heated bathroom floors, a/c, heat, modern kitchen, brand new appliances/washer dryer, sleeping loft, and separate storage loft. Location, location, location.
Popular amenities for Chappaquiddick family-friendly rentals
Family-friendly home rentals with a hot tub

18 Menemsha Rd., Popponesset, Pool, 3-Beds, 4 bath

Vineyard Meadow Writer's Cottage with Hot Tub

Oak bluffs cottage Perfect place to honeymoon!

Hideout at Water's Edge, 131 North Shore Blvd, #4

Awesome Cottage near Beach, Backyard Bar & Hot Tub

Lakefront Spa Retreat • Hot Tub • King Bed • Dock

Luxury House 0.25 mi from Craigville Beach

Valentine's Retreat Hot Tub Fire Pit Trails Beach
Family- and pet-friendly home rentals

gorgeous waterfront cottage w/4kayaks and 2 SUPs

Cheerful, Romantic Retreat for Two

★Waterview ★Pet Friendly ★Kayaks ★Trails ★

impeccable cottage STEPS to downtown OB & beach!

Beautiful clean walk to Town, Inkwell and harbor!

Charming Cape Near Beaches + Dog Friendly

Stunning Waterfront with Serene Sunrise Views!

Cape Cod; John’s Pond beach w/2 kayaks -SuperHost!
Family-friendly home rentals with a pool

Exclusive New Seabury Home w/ Heated Pool ⛳️🏖🦞☀️🐠

Beautiful Edgartown 3500 sq ft home, heated pool

Falmouth, Cozy Studio Near Old Silver Beach

Great Location. Near Beach & Main Street. Unit M1

Cape Cod Resort|Cabin w/Pool & Private Beach

Jolly Captain Lighthouse

CapeSearenity-Large Pool-Beach Passes-Family Fun!

Private Pool, near beaches, 3 BR/3 BA, Central Air
Destinations to explore
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- Family-friendly rentals United States
- Cape Cod
- Mayflower Beach
- West Dennis Beach
- Craigville Beach
- East Sandwich Beach
- Duxbury Beach
- Easton Beach
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- Bonnet Shores Beach
- Second Beach
- Coast Guard Beach
- The Breakers
- Pinehills Golf Club
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- New Silver Beach
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- Nickerson State Park
- Popponesset Peninsula
- Cahoon Hollow Beach
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- Fort Adams State Park
- Lighthouse Beach
- Cape Cod Inflatable Park





