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Up-Island Treehouse with Roofdeck and Waterviews

Photo gallery for Up-Island Treehouse with Roofdeck and Waterviews

A wooden deck with two striped lounge chairs and a small table.
A two-story wooden house with a gabled roof and a small porch.
A kitchen with a wooden countertop, a microwave, a stove, and a sink. There is a window with a view of trees, and a clock on the wall.
A living room with a wooden staircase, a yellow coffee table, and a colorful abstract painting on the wall.
A garden path leading to a house with a wooden fence and dense foliage.

Reviews

9.4 out of 10
Exceptional
2 bedrooms1+ bathroomSleeps 3

Popular amenities

  • Onsite parking available
  • Kitchen
  • Washing machine
  • Barbecue
  • Balcony
  • Free Wi-Fi

Explore the area

View map
Aquinnah, MA
  • Place, Gay Head Lighthouse
    ‪4 min drive‬
  • Place, Aquinnah Cliffs
    ‪4 min drive‬
  • Place, Squibnocket Pond
    ‪6 min drive‬
  • Airport, Vineyard Haven, MA (MVY-Martha's Vineyard)
    ‪35 min drive‬

Rooms & beds

2 bedrooms (sleeps 3)

Cozy Bedroom

1 Double Bed

Master Bedroom Loft

1 Queen Bed

1 bathroom, 1 half bathroom

Full Bath

Bathtub or shower · Bathtub · Toilet · Shower only

Half Bath

Toilet · Outdoor shower

Spaces

Deck or patio
Outdoor shower
Kitchen
Balcony
Dining area

About this property

Up-Island Treehouse with Roofdeck and Waterviews

Welcome to our getaway. The Up-Island Treehouse offers an open, light-filled and breezy spot on the western tip of Martha's Vineyard. Here you can relax and unwind in comfort and take your time to enjoy waterviews, birdsong and the pleasure of lazing a day away in a hammock. With decks on three levels, the house affords our guests time apart and time together; time in the sun and time in the shade. Our treehouse, as its name implies, is hidden in the trees and situated on 2 acres with old stone walls and a stream on the property. Guests enjoy lunches and dinners on the main deck,; sunsets on the roofdeck; an open and inviting master bedroom with full ensuite bath and easy proximity to Aquinnah's beaches. The house has 2 bedrooms and 1 1/2 baths. The master loft boasts a Schifman queen and quality linens and the first level boasts a well-placed open air outdoor shower that our guests describe as special. The house is biking distance to all Gay Head beaches and includes permission to access Philbin Beach passes. Wifi is included.

During Covid, the house will be unoccupied for 2 days between renters. The house will be professionally cleaned before guests' arrival.

This house is featured in 'Unique Rentals' on the MassLive website.

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House Rules

Check in after 3:00 PM
Check out before 10:00 AM
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Children

Children allowed: ages 13–17
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Events

No events allowed
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Pets

No pets allowed
Owner allergies. No pets permitted on premises.
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Smoking

Smoking is not permitted
There is no smoking permitted on the premises.
Trash removal is old vineyard. Guest will remove all of their trash. The entire security deposit is forfeited if any bags of trash are left behind.
Bring lounge chair cushions inside if rain is expected. Max occupancy is 8 people. Max overnight is 3 unless prearranged. Events are not permitted.
Flush for septic (toilet paper only). Sorry, no pets allowed. No smoking.

Important information

You need to know

Property Registration Number C1332111111
Property # 3602589
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Aquinnah

Located in Aquinnah, this holiday home is near the beach. Island Cove Miniature Golf and Island Cove Adventures are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Chilmark Chocolates and Fulling Mill Brook Preserve. The Grey Barn and Farm and Polly Hill Arboretum are also worth visiting. Discover the area's water adventures with kayaking and sailing nearby, or enjoy the great outdoors with hiking and horse riding.
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Map
Aquinnah, MA

What's nearby

  • Gay Head Lighthouse - 4 min drive - 2.6 km
  • Aquinnah Cliffs - 4 min drive - 2.6 km
  • Squibnocket Pond - 6 min drive - 4.2 km
  • Menemsha Beach - 12 min drive - 6.7 km
  • Lucy Vincent Beach - 15 min drive - 12.7 km

Getting around

  • Vineyard Haven, MA (MVY-Martha's Vineyard) - 27 min drive

Restaurants

  • ‪Menemsha Galley - ‬16 min drive
  • ‪Home Port Restaurant - ‬15 min drive
  • ‪Chilmark Tavern - ‬12 min drive
  • ‪Aquinnah Shop - ‬5 min drive
  • ‪Beach Plum Inn & Restaurant - ‬15 min drive

Frequently asked questions

Is Up-Island Treehouse with Roofdeck and Waterviews pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Up-Island Treehouse with Roofdeck and Waterviews?

As of 3 September 2026, prices found for a 1-night stay for 2 adults at Up-Island Treehouse with Roofdeck and Waterviews on 5 September 2026 start from NZ$49,678, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Up-Island Treehouse with Roofdeck and Waterviews?

On-site parking is available at the property.

What time is check-in at Up-Island Treehouse with Roofdeck and Waterviews?

Check-in begins at 3:00 PM.

What time is check-out at Up-Island Treehouse with Roofdeck and Waterviews?

Checkout is at 10:00 AM.

Where is Up-Island Treehouse with Roofdeck and Waterviews located?

Situated by the sea, this holiday home is within 3 miles (5 km) of Gay Head Lighthouse, Aquinnah Cliffs and Edys Island. Squibnocket Pond and Stonewall Beach are also within 6 miles (10 km).

About the host

Hosted by Dana An

Host profile image
I live and work in Boston, Massachusetts. I like to read, hike, cook. On the island I bike and rollerblade and try to get to Philbin around 3 in the afternoon. Some of my favorite things about Martha's Vineyard are Squibnocket Beach, Menemsha, the West Tisbury Farmer's Market, the farms and pasture lands and the birdsong.

Why they chose this property

We bought this house at a time of real estate mayham on the island. There were few (or no) shared real estate listings and we were led to believe that this was the only home in Gay Head for sale in our price range. It was a headache of a purchase but we persisted. It is quiet, there are a million stars at night, Philbin Beach is beautiful. We bought this house from Nancy Dwyer who was the original owner of the house.

What makes this property unique

The entire house is unique. It has a fun layout with a master bedroom loft. It has a great (though finicky) stove and the open kitchen/dining living area has a spacious, inviting feel. There is 2-acre zoning in the area and only 2 neighbors drive beyond our house to get to their houses.

Languages:

English
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