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Cuttyhunk Waterfront
Gosnold, Massachusetts

Wander Cuttyhunk Waterfront

Wander Cuttyhunk Waterfront

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8 guests

4 beds

2.5 bathrooms

1/70

BalconyWaterfrontBBQ Area

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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Flexible check-in & out

Check-in after 4:00pm • Check-out before 10:00amNo pets allowed

Easy cancellation

Cancel within 24 hours for a full refund.

Pristine homes, no to-do lists

Arrive to five star cleaning • No chores at checkout • Just lock up and go

About the property

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.

Hotel-grade amenities

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.

Common Amenities

  • Wifi
  • Balcony
  • Free parking
  • Waterfront
  • Patio
  • Fire extinguisher
  • Smoke detector
  • Hot water
  • First aid kit
  • Air conditioning
  • Carbon monoxide detector

Deck

  • BBQ Area
  • BBQ Utensils
  • Outdoor shower
  • Outdoor seating

Dining Room

  • Dining table

Kitchen

  • Oven
  • Cooking basics
  • Stove
  • Microwave
  • Freezer
  • Fridge
  • Dishwasher
  • Dishes
  • Coffee maker
  • Coffee
  • Kettle
  • Tea
  • Spices
  • Silverware
  • Cleaning supplies
  • Wine glasses

Common Area

  • Movie projector

Bedroom 1

  • Bed linens
  • Closet
  • Hangers

Bedroom 2

  • Bed linens
  • Closet
  • Hangers

Bedroom 3

  • Bed linens
  • Closet
  • Hangers

Bedroom 4

  • Bed linens
  • Closet
  • Hangers

Bathroom 1

  • Bath linens
  • Toilet
  • Shower
  • Shower gel
  • Shampoo
  • Conditioner
  • Body soap
  • Bathtub

Bathroom 2

  • Bath linens
  • Toilet
  • Shower
  • Shower gel
  • Shampoo
  • Conditioner
  • Body soap

Half Bath

  • Bath linens
  • Half bath
  • Toilet
  • Body soap

Laundry Room

  • Washer
  • Dryer
  • Cleaning supplies

Where you’ll sleep

Bedroom 1

1 queen bed

Bedroom 2

1 full bed

Bedroom 3

1 queen bed

Bedroom 4

1 queen bed

Bedroom 1
1 queen bed
Bedroom 2
1 full bed
Bedroom 3
1 queen bed
Bedroom 4
1 queen bed

Where you’ll be

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.

Gosnold, Massachusetts, United States
41.4285439-70.92972879999999
Timezone: America/New_York

Restaurants

Cuttyhunk Fishing Club

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

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

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

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.

Attractions

Penikese Island

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

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

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.

Cuttyhunk Historical Society

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

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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Wander Guarantee Badge

Guests love Wander

Wander's average ratings

Cleanliness
4.8
Location
4.9
Check-in
4.8
Value
4.8
Concierge Quality
4.8
Wow Factor
4.9

Have a question?

24/7 Concierge

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Things to know

Here are some things which you should know before booking Wander Cuttyhunk Waterfront

HOUSE RULES

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

CANCELLATION POLICY

Cancel within 24 hours for a full refund.

Before you book

Availability & Pricing

DatePrice (USD, excl. fees and taxes)Availability
Dec 23, 2025$592Available
Dec 24, 2025$592Available
Dec 25, 2025$592Available
Dec 26, 2025$592Available
Dec 27, 2025$592Available
Dec 28, 2025$592Available
Dec 29, 2025$592Available
Dec 30, 2025$592Available
Dec 31, 2025$592Available
Jan 1, 2026$546Available
Jan 2, 2026$546Available
Jan 3, 2026$546Available
Jan 4, 2026$400Available
Jan 5, 2026$400Available
Jan 6, 2026$400Available
Jan 7, 2026$400Available
Jan 8, 2026$400Available
Jan 9, 2026$500Available
Jan 10, 2026$500Available
Jan 11, 2026$400Available
Jan 12, 2026$400Available
Jan 13, 2026$400Available
Jan 14, 2026$400Available
Jan 15, 2026$400Available
Jan 16, 2026$564Available
Jan 17, 2026$564Available
Jan 18, 2026$570Available
Jan 19, 2026$570Available
Jan 20, 2026$400Available
Jan 21, 2026$400Available
Jan 22, 2026$400Available
Jan 23, 2026$500Available
Jan 24, 2026$504Available
Jan 25, 2026$400Available
Jan 26, 2026$400Available
Jan 27, 2026$400Available
Jan 28, 2026$400Available
Jan 29, 2026$401Available
Jan 30, 2026$540Available
Jan 31, 2026$540Available
Feb 1, 2026$410Available
Feb 2, 2026$414Available
Feb 3, 2026$419Available
Feb 4, 2026$423Available
Feb 5, 2026$428Available
Feb 6, 2026$570Available
Feb 7, 2026$576Available
Feb 8, 2026$432Available
Feb 9, 2026$437Available
Feb 10, 2026$437Available
Feb 11, 2026$441Available
Feb 12, 2026$441Available
Feb 13, 2026$678Available
Feb 14, 2026$684Available
Feb 15, 2026$684Available
Feb 16, 2026$684Available
Feb 17, 2026$446Available
Feb 18, 2026$446Available
Feb 19, 2026$450Available
Feb 20, 2026$600Available
Feb 21, 2026$600Available
Feb 22, 2026$450Available
Feb 23, 2026$450Available
Feb 24, 2026$450Available
Feb 25, 2026$450Available
Feb 26, 2026$450Available
Feb 27, 2026$600Available
Feb 28, 2026$600Available
Mar 1, 2026$450Available
Mar 2, 2026$450Available
Mar 3, 2026$450Available
Mar 4, 2026$450Available
Mar 5, 2026$450Available
Mar 6, 2026$625Available
Mar 7, 2026$625Available
Mar 8, 2026$450Available
Mar 9, 2026$450Available
Mar 10, 2026$450Available
Mar 11, 2026$450Available
Mar 12, 2026$450Available
Mar 13, 2026$625Available
Mar 14, 2026$625Available
Mar 15, 2026$450Available
Mar 16, 2026$450Available
Mar 17, 2026$450Available
Mar 18, 2026$450Available
Mar 19, 2026$450Available
Mar 20, 2026$625Available
Mar 21, 2026$625Available
Mar 22, 2026$450Available
Mar 23, 2026$450Available
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