The first time I saw this house, I was struck by three things: the way the house blends in to the land around it, the windows and the deck! The colors of the exterior effortlessly to blend in with the sand, the stone wall and the surrounding trees. The windows reflect and become part of the sky overhead.

And the windows that are so captivating from the outside, are better from the inside with views of Vineyard Sound, sunsets and star-filled Vineyard night skies. The house sits atop a hill, making the views even more breathtaking. The floor to ceiling windows also provide an extraordinary amount of light to the interior, so you’ll never be far from the Island sun.

The deck is quite luxurious and paired with the swimming pool set behind the house and this huge kitchen, this vacation rental is a great spot to entertain. The house itself sleeps eight with four bedrooms and three full baths. And, if you need more than a pool, Philbin and Lobsterville Beaches are within 1.5 miles of the house which is located on Sandcastle Lane – how much more dreamy does it get?

Contact me for more information or to book this Martha’s Vineyard waterfront vacation rental!

It’s true, it’s a long haul all the way to the cliffs of Aquinnah (formerly Gay Head) on Martha’s Vineyard, but it pays off. Breathtaking views of the ocean, a tiny little island town, beaches for miles, a 212 year old lighthouse and, of course, the cliffs, swirls of red and orange clay cascading down into the beautiful Atlantic ocean.

The little town atop the cliffs is most commonly referred to as The Aquinnah Circle. In the summertime and fall the circle is full of little souvenir shops that sell adorable island treasures, especially Wampum bracelets, necklaces and earrings.

Also in the circle you can find the delicious Aquinnah Restaurant.  Operated and run by two Wampanoag families, the restaurant is open from mid-April to mid-October. A favorite breakfast is the Tomahawk special, which consists of two homemade fish cakes atop poached eggs, covered with salsa and melted cheddar cheese. They also serve lunch, a variety of sandwiches, burgers and delicious salads. Dinner entrees consist of a large array of island seafood including scallops, mussels, striped bass, shrimp, lobster and much more.

If you’re looking to stay in Aquinnah, try the Outermost Inn. Run by the island’s own Taylor family (yes, as in James)!  For more information visit their website.

Aquinnah is most popular in the summertime while it is busy and bustling, but even in the offseason a long walk on the beach in one of nature’s most beautiful island locations is dynamic.

If you choose to rent a house up-island in Aquinnah, we have many to choose from, like this:

Expect quiet, amazing sunsets and sweeping views.

Some handy terms and quick explanations you should know so that you can find your way around the island and sound like an islander…

1. You are going for a vacation ‘on’ the Vineyard, not ‘in’ or ‘at’ the Vineyard.
2. ‘Chappy’ is short for Chappaquiddick, not what happens to your lips when you’ve been out in the sun for too long. Chappaquiddick is a small island that lies off the eastern tip of Martha’s Vineyard and is part of Edgartown. You can get to Chappy via a small ferry that holds a couple of cars and a bunch of people and bikes. It’s a great day trip from the Vineyard. Don’t forget to pack a lunch!
3. 5 Corners is an adventuresome intersection in downtown Vineyard Haven. It is called 5 Corners because there are 5 streets that form the intersection. Move with caution as only 3 of the approaching roads have stop signs and the other 2 have the right of way. Drive slowly, be nice, enjoy this quirky attraction, and you’ll be just fine.
4. ‘Squibby’ is short for one of the island’s beach treasures, Squibnocket, located in Chilmark as you head towards Aquinnah.
5. The ‘Flying Horses’ make up the country’s oldest horse carousel. They are beautiful and an island highlight right in downtown Oak Bluffs.
6. ‘Gay Head’ is now called ‘Aquinnah’ and it is the town at the farthest end from the ferries. It is the home of the Wampanoag Native American tribe and the stunning Aquinnah cliffs.
7. ‘Quahog’s’ are clams….so Martha’s Vineyard’s quahog chowdah is clam chowdah – only better.