And if the Obamas feel out of place among the Hollywood elite, fear not, there are plenty of Washington, D.C., regulars on the island, too.
Former President Clinton was spotted golfing last weekend, and the rest of his family is rumored to be in tow.
Speaker of the House Nancy Pelosi is also expected to visit this summer.
"The people who come here are very accomplished in whatever they decide to pursue," said Bellante-Holand of the eclectic mix of people who travel to the island. "That makes for some great chance meetings."
So what does the Vineyard offer these celebrities who remain loyal to the island year after year?
Despite the opportunity to stalk your favorite celebrity, locals on the island really respect the stars' space, said Bellante-Holand.
"Everyone here tries to value the privacy of the people who visit here, and that's one of the reasons it's such a popular vacation spot for stars," she said. "It makes it very easy to enjoy themselves and enjoy their friends or family who come with them."
Nancy Gardella, the executive director of the Martha's Vineyard Chamber of Commerce, says that it's the escape from the lens of intrusive photographers that makes Martha's Vineyard so appealing.
"They can move around and be themselves and people are pretty laid back," she said. "They can have a real family vacation without having to worry about being chased down by paparazzi."
As for the stars that Malia and Sasha Obama might like to see, there's no word yet on the chance of a Jonas Brothers sighting.