Family-friendly vacation rentals in Chappaquiddick

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!

Private Garden Oasis -Outdoor Shower- 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

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.

Chappy Beach House

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.

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!

Beachfront Cottage + Studio w. Town Access

Welcome to The Rudder Cottage! Fully renovated 1930's cottage on an ocean front compound, with a picturesque porch overlooking the outer harbor, full basement with washer/dryer and central air. An additional detached studio provides a third bedroom/work space. Stunning views of the Edgartown lighthouse and Cape Poge. Access to 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!

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.

Chappaquiddick Island - Whispering Pines

Peace and quiet, and access to fabulous East Beach, Mytoy, Wasque and the many wonderful walking trails of Chappaquiddick, this lovely home among "whispering Pines" will be your warm welcoming retreat after a day at the beach, exploring Chappy by bike or fishing to your hearts delight. We provide a comfy, well furnished and beautifully decorated home outfitted with all cotton bedding, linens and fresh pillows, and lovely quilts, wool and cotton rugs, and so much more.

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.

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!

Madaket Bright and Airy Guest Cottage

Escape to this charming guest cottage in Madaket, just a short walk from Madaket Beach, known for its stunning sunsets. This peaceful retreat offers a cozy, light-filled space with a well-equipped kitchen and comfortable sleeping arrangements. Enjoy mornings on the private patio, bike scenic paths, or dine at Millie’s. Easily explore Nantucket’s shops, restaurants, and history. End your day with a breathtaking sunset—your perfect island getaway awaits!

Modern & Spacious Edgartown Home with Pool

Enjoy your vacation in this wonderfully charming three bedroom home with an in-ground heated pool. Head to the beach or stay at home and go for a swim in your own backyard. There is plenty of dining room & deck space to entertain. The bike path and bus shuttle are at the end of the road (a two minute walk away). Downtown Edgartown is less than two miles away for you to enjoy shopping and multiple dining choices.