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8 guests
4 beds
2.5 bathrooms
8 guests
4 bedrooms
4 beds
2.5 bathrooms
1956 sq. ft.
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.
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 offers a charming seaside breakfast experience with classic American dishes served on a veranda overlooking the harbor, blending historic island ambiance with fresh, hearty meals. Its scenic views and cozy atmosphere make it a must-visit on Cuttyhunk Island.
Cuttyhunk Raw Bar offers fresh, locally harvested oysters, clams, and classic New England seafood like chowder, served right at the fishing dock or delivered to your boat for a laid-back island dining experience. Enjoy the unique flavors of Cuttyhunk in a casual, waterside setting.
Cuttyhunk Lobster Shack offers fresh, classic seafood like steamed lobster and clams in a casual, seaside setting right by the fishing dock—perfect for enjoying a relaxed meal on the island or taking it back to your boat.
Soprano's Pizza serves delicious, high-quality pizzas with fresh ingredients and fast delivery, offering a variety of options including gluten-free and vegan choices in a friendly, casual setting. It's a local favorite known for great taste and excellent service.
Penikese Island offers a rare blend of serene hiking, exceptional birdwatching with over 150 species, and vibrant snorkeling in pristine waters, perfect for nature lovers and adventurous explorers seeking a unique New England island experience.
Cuttyhunk Pond Docks offer a peaceful spot for boating enthusiasts and nature lovers to launch kayaks, fish, or simply enjoy the scenic harbor views. It’s perfect for those seeking a relaxing water adventure amid the island’s charming, historic setting.
Lookout Park offers breathtaking panoramic views from high atop Lookout Mountain, where you can see up to seven states on a clear day—perfect for families, photographers, and anyone who loves natural beauty and a bit of adventure. Its scenic overlooks and unique rock formations make it a memorable stop for all ages.
Step into the heart of Cuttyhunk’s past at the Historical Society, where fascinating exhibits and island stories bring local heritage to life—perfect for curious travelers and history lovers eager to connect with the unique culture and maritime legacy of this charming island community.
Peak Chum Mountain offers a rewarding hike with stunning panoramic views, perfect for outdoor enthusiasts who enjoy a mix of challenging trails and natural beauty. It’s ideal for hikers seeking a peaceful mountain escape with impressive scenery.
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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.
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Jan 24, 2026 | $500 | Available |
| Jan 25, 2026 | $400 | Available |
| Jan 26, 2026 | $400 | Available |
| Jan 27, 2026 | $400 | Available |
| Jan 28, 2026 | $400 | Available |
| Jan 29, 2026 | $400 | Available |
| Jan 30, 2026 | $500 | Available |
| Jan 31, 2026 | $500 | Available |
| Feb 1, 2026 | $400 | Available |
| Feb 2, 2026 | $400 | Available |
| Feb 3, 2026 | $400 | Available |
| Feb 4, 2026 | $400 | Available |
| Feb 5, 2026 | $400 | Available |
| Feb 6, 2026 | $500 | Available |
| Feb 7, 2026 | $500 | Available |
| Feb 8, 2026 | $400 | Available |
| Feb 9, 2026 | $400 | Available |
| Feb 10, 2026 | $400 | Available |
| Feb 11, 2026 | $400 | Available |
| Feb 12, 2026 | $400 | Available |
| Feb 13, 2026 | $500 | Available |
| Feb 14, 2026 | $500 | Available |
| Feb 15, 2026 | $465 | Available |
| Feb 16, 2026 | $465 | Available |
| Feb 17, 2026 | $400 | Available |
| Feb 18, 2026 | $400 | Available |
| Feb 19, 2026 | $400 | Available |
| Feb 20, 2026 | $500 | Available |
| Feb 21, 2026 | $500 | Available |
| Feb 22, 2026 | $400 | Available |
| Feb 23, 2026 | $400 | Available |
| Feb 24, 2026 | $400 | Available |
| Feb 25, 2026 | $400 | Available |
| Feb 26, 2026 | $400 | Available |
| Feb 27, 2026 | $500 | Available |
| Feb 28, 2026 | $500 | Available |
| Mar 1, 2026 | $400 | Available |
| Mar 2, 2026 | $400 | Available |
| Mar 3, 2026 | $400 | Available |
| Mar 4, 2026 | $400 | Available |
| Mar 5, 2026 | $400 | Available |
| Mar 6, 2026 | $500 | Available |
| Mar 7, 2026 | $500 | Available |
| Mar 8, 2026 | $400 | Available |
| Mar 9, 2026 | $400 | Available |
| Mar 10, 2026 | $400 | Available |
| Mar 11, 2026 | $403 | Available |
| Mar 12, 2026 | $403 | Available |
| Mar 13, 2026 | $509 | Available |
| Mar 14, 2026 | $509 | Available |
| Mar 15, 2026 | $412 | Available |
| Mar 16, 2026 | $412 | Available |
| Mar 17, 2026 | $412 | Available |
| Mar 18, 2026 | $416 | Available |
| Mar 19, 2026 | $416 | Available |
| Mar 20, 2026 | $520 | Available |
| Mar 21, 2026 | $520 | Available |
| Mar 22, 2026 | $416 | Available |
| Mar 23, 2026 | $420 | Available |
| Mar 24, 2026 | $420 | Available |
| Mar 25, 2026 | $420 | Available |
| Mar 26, 2026 | $420 | Available |
| Mar 27, 2026 | $525 | Available |
| Mar 28, 2026 | $525 | Available |
| Mar 29, 2026 | $420 | Available |
| Mar 30, 2026 | $420 | Available |
| Mar 31, 2026 | $420 | Available |
| Apr 1, 2026 | $495 | Available |
| Apr 2, 2026 | $495 | Available |
| Apr 3, 2026 | $650 | Available |
| Apr 4, 2026 | $650 | Available |
| Apr 5, 2026 | $495 | Available |
| Apr 6, 2026 | $495 | Available |
| Apr 7, 2026 | $495 | Available |
| Apr 8, 2026 | $495 | Available |
| Apr 9, 2026 | $495 | Available |
| Apr 10, 2026 | $650 | Available |
| Apr 11, 2026 | $650 | Available |
| Apr 12, 2026 | $495 | Available |
| Apr 13, 2026 | $495 | Available |
| Apr 14, 2026 | $495 | Available |
| Apr 15, 2026 | $495 | Available |
| Apr 16, 2026 | $495 | Available |
| Apr 17, 2026 | $650 | Available |
| Apr 18, 2026 | $650 | Available |
| Apr 19, 2026 | $495 | Available |
| Apr 20, 2026 | $495 | Available |
| Apr 21, 2026 | $495 | Available |
| Apr 22, 2026 | $495 | Available |
| Apr 23, 2026 | $495 | Available |
| Apr 24, 2026 | $650 | Available |