With a population density of fewer than 50 people per square mile – the lowest on Martha’s Vineyard – Chilmark is truly a place to get away from it all. It’s been the favored vacation spot of President Obama and his family, and it’s easy to see why. It offers sprawling farmland, elegant residences, and wooded and grassland properties bordered by miles of centuries-old stone walls. Search for the perfect rental below. You can also view all of our Martha's Vineyard Vacation Rentals. Or search for rentals in Edgartown, Edgartown Village, Katama, Oak Bluffs, Vineyard Haven Tisbury, or West Tisbury.