Spectacular Chilmark Sunset Water Views, Walk to Private Beach, Trails, Tennis!

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We have transferrable car ferry reservations ⛴ for guests who would like to book for summer 2026 . Just reach out to us. ***

This charming, rustic cottage is located on Martha's Vineyard iconic north shore with views of Vineyard Sound and the Elizabeth Islands. Located in quiet, pastoral Chilmark, the 40-foot deck has spectacular sunset water views. Follow the path from the backyard down to 3/4 of a mile of private association beach on Vineyard Sound. Enjoy miles of walking trails and access to two association tennis courts. With 4 bedrooms, 2 bathrooms, and an outdoor shower, it comfortably sleeps 8. Air conditioning, high speed internet, and access to Chilmark's famous private beaches (Lucy Vincent, Squibnocket, and Menemsha Pond) make this home an ideal destination for your next vacation!

Please note that there is a 7-night minimum stay and Friday is the turnover day.

What to Expect

When you arrive at Chilmark Cottage, the first thing you will notice is the view. Virtually every room in the house has a water view. Multiple sets of sliding glass doors provide exquisite views of the water and easy access to the deck, which spans the entire back of the house. The deck has a grill and a dining area that comfortably seats 8.

The main floor has two bedrooms. The front bedroom has a king-size bed. Across the hall is a full bath with a shower/tub combination. The back bedroom has a full-size bed, a desk, and views of the water. The kitchen, dining area, and living room complete the main floor and all have water views. The outdoor shower is located on the side of the house. A quaint circular staircase leads you upstairs where you will find two more bedrooms and a full bathroom with a shower stall. Each of the upstairs bedrooms has two twin beds (4 beds total) and views of the water.

Once you settle in, you’ll want to explore. Follow the backyard path down to a trail that leads to the private association beach. It’s about a five-minute walk. Or, if you prefer a bit more exercise, there are 3 miles of private walking trails around the association which can lead you over to Great Rock Bight Preserve’s public trails. There are also two private association tennis courts you can enjoy during your stay.

What Makes This Place Special

As one of the original homes in Spring Point, this remarkable piece of the Vineyard was lovingly passed down through the same family for over 50 years. They decided to sell it in 2022 and we knew right away that it was a rare gem. Sitting on over 3 acres of wooded north shore land, the home has stunning views of Vineyard Sound and the Elizabeth Islands. The sunsets from the back deck are nothing short of magical. There are over 68 acres of common land in Spring Point, 3 miles of walking trails, and 3/4 of a mile of private beach. We fell in love with this place the moment we saw it. Since acquiring it, we have taken great care to balance bringing in modern amenities while maintaining the home's rustic Chilmark charm. We hope you will love it as much as we do!

Unique Benefits

- Spectacular water views from virtually every room in the house.
- 5-minute walk to the beach (just follow the path from the backyard!).
- 3/4 of a mile of private association beach.
- Access to 2 private association tennis courts.
- 3 miles of private walking trails that also connect to Great Rock Bight Preserve.
- 40-foot-wide deck - perfect for dining, entertaining, or taking in the magical sunsets.
- Private, wooded lot on over 3 acres.
- Nestled in an association with over 68 acres of common land.
- Access to Chilmark's famous town beaches, including Lucy Vincent and Squibnocket.
- Zero light pollution, with millions of stars visible with the naked eye