Holiday Rentals in Chappaquiddick Island
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Holiday Rentals in Chappaquiddick Island

Sleeps 12, amazing view, tennis court, basketball court, beaches

The Club at New Seabury

Coastal chic meets French Provençal in this newly renovated oceanfront home.

InnSeason Resorts Captain's Quarters

Sea Mist Resort

Steps to the Ocean! Perfect Location!!!

LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

Newly Renovated Near Amazing Sunset Beach

Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome

Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Cozy getaway in a central location w/ a full kitchen & furnished deck

Beachside Village Resort

The quintessential MV home. Now booking for 2026!

Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

Steps to the beach with an ocean view,
Other types of properties in Chappaquiddick Island you may be interested in

Iris Hotel Cape Cod
Holiday Accommodation Chappaquiddick Island
You’re the type of person who wants to be right in the middle of it all, but still have your own space. You want to be able to take care of everything yourself, but also get plenty of R&R. Well, holiday rentals in Chappaquiddick Island are ready to roll out the welcome mat. We mean that literally—they probably do have a welcome mat. It’s all those little things that will make you fall in love with this type of accommodation, and with Chappaquiddick Island itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.
Chappaquiddick Island holiday houses have everything you could need in a place to stay, along with several things you probably never even thought you needed. Towels and linens? Check. Cooking utensils? Check. Dog treats for the pupper? Well, you might want to bring your own to your pet-friendly holiday house, just in case. (He’s a picky little prince anyway, right?) But otherwise you’re good to go. You might even find some games for the little ones, if you’re bringing the family along.
If you are bringing the kids, don’t let that dissuade you from looking for the finer things. Luxury is the name of the game in Chappaquiddick Island, and house accommodation is no different. Sure, it should feel like a home away from home—but more like a really fancy home, where you don’t have to worry about cleaning or mowing the lawn. Yes, it’s as great as it sounds.
Make your next getaway truly your own. We’ve got plenty of holiday accommodation in Chappaquiddick Island with your name on it, so pack up your favourite books, wine and that playlist of summer hits from 2003. It’s your time to shine.
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