Family-friendly vacation rentals in Chappaquiddick

Arrowsmith Cottage-Oak Bluffs. Aug 15-22 now open!

Welcome to Arrowsmith Cottage! If you are considering bringing your pet, please note - 1 small dog will be considered, but please first contact me directly (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 pets require homeowner's written approval and guest’s agreement to the pet fee (generally $100 per stay) and homeowners’ pet rules. Hosts are not responsible for listing inaccuracies due to Airbnb's own input or AI.

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.

Outdoor Shower, Private Garden Patio, Walk to town

* 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

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

Martha’s Vineyard Cottage - A Glamping Experience!

This is your vineyard home, where you can walk or ride a bike less than a mile to the beach or two into town. Get the glamping experience with kitchenette, A/C, an outdoor shower, a composting toilet, a queen bed in the loft and futon couch that can sleep two more in the living room. Enjoy outdoor games, outdoor seating, a Weber grill for bbq, tv, WiFi, cozy indoor space and more, right on the bike path with a bus stop for easy accessibility or free car parking. Whatever you want!

Chappaquidick contemporary cottage with sauna

This unique place has a style all its own. Contemporary 3 bedroom 2 bathroom home in heart of chappaquidick island . Off the main road close to Mytoi garden , waque and dike bridge. Bike to the beach . And best of it all is the Outdoor shower . Just ferry ride To Edgartown to enjoy morning stroll or have dinner. Equipped with echelon cycling bike sauna and ping pong table. Enjoy bbq on deck .washing machine and dryer available for use All bed have linen and quilt blankets.

Cottage suite between the harbors: no minimum stay

Nestled between Oak Bluffs and Vineyard Haven harbors, our relaxing suite is a perfect way to extend your weekly rental, or to enjoy a day or two on this special island we call The Rock. Our cozy guest suite, newly renovated has two bedrooms, living space, kitchenette, full bath, deck with grill, outdoor shower, and footwash (hot H20), W/D (in unit) and a private entrance. An easy walk to town and beaches. Parking is available in our driveway. Enjoy our historic home!

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.

Mink Cove Treehouse

A unique adult adventure awaits in this cozy hand crafted tree house! Nestled 12 feet off the ground amongst the chirping birds, red oaks & breathtaking views of Mink Cove in Buzzards Bay. The tree house is accessible by a suspension bridge that leads you to a partially covered porch where you can enjoy a cup of coffee or sit back & take in the sunset with a glass of wine. Step inside to the living space & snuggle up on the couch for an intimate evening.

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!

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!

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!