Wander Cuttyhunk Waterfront

Wander Cuttyhunk Waterfront is a secluded island retreat designed for true escape—think decompressing, disconnecting, and reconnecting with the people who matter most. Set on the water with private direct beach and boating access, the home’s generous south-facing deck offers expansive views of the harbor and Gay Head on Martha’s Vineyard, along with sunrise light that fills the house throughout the day. Follow the path down to your own sandy beach, perfect for kayaking, boating, fishing, or swimming with children and friends, or take a short walk or golf cart ride to nearby Churches Beach on the Atlantic Ocean. After a day in the sun, unwind back at the house with a casual movie night in the bonus media room, fire up the BBQ, or rinse off in the outdoor shower and savor the calm of island living.

Nestled on Cuttyhunk Island, this location provides peaceful access to protected harbor waters, beautiful beaches, and scenic hiking trails. Guests can spend their days kayaking or paddleboarding through calm coves, sailing along the Elizabeth Islands, or fishing in some of the region’s most pristine waters. The island’s charming village atmosphere invites leisurely walks to the local market, ice cream stand, and historic church, while nearby lookout points offer breathtaking sunset views across Buzzards Bay.

EQUIPMENT RENTAL
The island is only accessible by ferry, so cars cannot be brought over. Golf carts are the main mode of transportation—reserve one in advance or arrange luggage transport for a smooth arrival. Reach out to us after your booking if you need assistance.

ACCESSIBILITY
Ferry service to Cuttyhunk is limited until May, operating only on Mondays and Fridays. Please confirm times before booking your stay. The current schedule is as listed below:

Monday
9:00 AM New Bedford to Cuttyhunk
2:00 PM Cuttyhunk to New Bedford

Friday
9:00 AM New Bedford to Cuttyhunk
2:00 PM Cuttyhunk to New Bedford

Times are subject to change. Cancelations or rescheduling may occur depending on weather conditions. Check the current schedule here: Cuttyhunk Ferry Co. Schedule

PWD Accessibility
This home contains features that may be difficult for elderly and guests with mobility challenges - including climbing a set of stairs to access additional levels.

NO PETS
This is a pet-free hypoallergenic space. No pets are allowed inside the home to maintain a hypoallergenic area as much as possible for our guests’ comfort.

WILDLIFE WARNING
The island is home to a variety of amazing creatures. It is incredible for those who love to nature-watch from afar, but may not be for everyone. Use caution and do not touch wildlife. Avoid leaving food outside (including residue in grills or fires), secure all garbage, and keep doors and windows closed.

NOISE
We kindly ask that you refrain from hosting parties or creating excessive noise during your stay, as we strive to maintain a peaceful environment for both our guests and neighbors. Amplified outdoor sounds are strictly prohibited.

AMENITIES
Food, Supplies & Island Services

We recommend bringing groceries and any essentials you’ll want for your stay. There is a small island market open in season (generally from before Memorial Day through after Columbus Day), but it carries only basic items and may not always be fully stocked.

Please note that Cuttyhunk is a dry island, so alcohol is not sold anywhere on the island. If you’d like to enjoy drinks during your stay, be sure to bring them with you.

SECURITY
For security, there are cameras on the shed, the corner of the property, and a Ring camera on the front door. There are no cameras inside the home.