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8 guests
4 beds
2.5 bathrooms
8 guests
4 bedrooms
4 beds
2.5 bathrooms
Wander Cuttyhunk Waterfront is a secluded island retreat designed for true escape—think decompressing, disconnecting, and reconnecting with the people who matter most.

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Check-in after 4:00pm • Check-out before 10:00am • No pets allowed
Cancel within 24 hours for a full refund.
Arrive to five star cleaning • No chores at checkout • Just lock up and go
Wander is the best of both worlds. The quality of a luxury hotel with the comfort of a private vacation home just for you and your guests.
BBQ Area
Balcony
Waterfront
Patio
Free parking
Wifi
Washer
Dryer
Hot water
Bedroom 1
1 queen bed
Bedroom 2
1 full bed
Bedroom 3
1 queen bed
Bedroom 4
1 queen bed
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.
Cuttyhunk Fishing Club
Cuttyhunk Raw Bar
Cuttyhunk Lobster Shack
Penikese Island
Cuttyhunk Pond Docks
Lookout Park
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Here are some things which you should know before booking Wander Cuttyhunk Waterfront
Check-in: after 4:00 pm
Check-out: before 10:00 am
8 guests maximum
No pets allowed
No smoking - fees will apply
Events require approval
Cancel within 24 hours for a full refund.
Check-in: after 4:00 pm
Check-out: before 10:00 am
8 guests maximum
No pets allowed
No smoking - fees will apply
Events require approval
The island is home to a variety of wildlife, including deer and coyotes, which are generally shy but should be observed from a distance. Please don’t leave small children or pets unattended outdoors at night.
As is common in the region, sharks have been sighted in surrounding waters, though there have been no reported incidents on Cuttyhunk. Guests should follow local beach advisories and posted signage. Ticks and mosquitoes are present seasonally; insect repellent and tick checks are recommended.
To help keep wildlife away, avoid leaving food outside, secure all trash, and keep doors and windows closed when not in use.
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.
Important Ferry & Travel Information
Cuttyhunk Island is only accessible by ferry. Since cars cannot be transported to the island, all guests will travel on foot via ferry. Because of this, it’s important to plan your arrival and departure around the ferry schedule.
Current Ferry Schedule (Limited Service Until May):
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
Ferry times can change, and trips may be delayed or canceled due to weather, so please double-check the schedule before finalizing your reservation.
You can view the full schedule here:
https://cuttyhunkferryco.com/schedule/
Since alternative transportation is very limited, we recommend confirming ferry availability in advance to ensure a smooth and stress-free stay.
Weather Advisory
During periods of rough weather or strong tides, the ferry schedule may shift, and delays or cancellations can happen. To keep things smooth, we recommend building a little flexibility into your travel plans and checking for ferry updates as your trip approaches.
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.
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.
Golf Cart Rentals
Dale Lynch: 774-451-2889
Ginny: 508-264-1988
This home follows a strict maximum occupancy rule of 8 guests. Please make sure that the total number of guests accompanying you (including both children and adults) doesn’t exceed the indicated maximum occupancy above to avoid cancellation of your stay and additional fees.
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.
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.