Despite considerable local buzz that the Obamas would stay in Oak Bluffs, a scenic enclave on the north coast of the island that is a popular vacation spot for African-Americans, the family will stay at Blue Heron Farm, a nearly 30-acre farm in Chilmark.
The farm, located on the southwestern side of the island, is secluded and will give the Obama family privacy that was not in great supply last year in Hawaii.
Last December, then president-elect Obama and his family vacationed in Hawaii and, without permission, a photographer was able to get within 150 feet and snap pictures of the Obamas sporting bathing suits and vacation wear.
Chilmark is more remote and secluded than other popular tourist spots on the Vineyard.
"Chilmark is the most reclusive, exclusive (town). That's where people really go to relax and unwind," said Dawn Bellante-Holand, general manager of Martha's Vineyard Online. "It's very laid back with a lot of the Hollywood types. It's where people really go to get away from it all."
The Blue Heron Farm is surrounded by other similar properties and the Obamas will have plenty of privacy if they choose to remain out of the public eye.
No other vacationers will be staying on the massive estate while the Obamas are there, due to security and the presidential entourage of staff and Secret Service.
Blue Heron Farm is owned by Mississippi developer William Van Devander, who was willing to take Obama's money for the vacation rental but donated to his opponent, Sen. John McCain, R-Ariz., in last year's presidential election.
In 1998, then-President Bill Clinton and his wife Hillary attended a party at the farm hosted in his honor by a former owner who died in a plane crash with his wife in 2003.
This isn't just any farm. The waterfront estate is located on the island's rural west end on West Tisbury Great Pond and was purchased by Devender for $20 million in 2005. The property features a five-bedroom, five-bath main house, guest quarters, swimming pool, barn and horse paddocks, apple orchard and boat house.
"It's the type of place that once you get there, it's not something you want to leave," said Vineyard real estate agent Tom Wallace, of Wallace and Company Sotheby's International Realty. "It's very tranquil, great place for a family vacation. The kids will absolutely have a ball as I'm sure Bo will also."
"It has very much of an old world feel to the property," he said.
Wallace would not disclose how much the Obamas are paying for the rental property.
Martha's Vineyard realtor Caroline Taylor, of Caroline Taylor Properties, estimates that the property would likely be rented for between $35,000 and $50,000.
White House press secretary Robert Gibbs said the Obamas will foot the bill for their vacation, as they have in the past including the trip he took as president-elect.
"I know that the Obamas are paying for their vacation, like they paid for a vacation last August in Hawaii and last December in Hawaii, as well," Gibbs said.
Remaining costs, for White House staff and Secret Service protection, will be handled as they are for other presidential travel, with taxpayer money.
All recent presidents have taken some time in August for a little rest and relaxation and their choice of destination can perhaps tell us something about their personality and their presidency.