Martha’s Vineyard, Massachusetts
The Place: No matter where you settle down on this famous vacation island, a feeling of quiet seclusion will grab you. The problem is getting there — especially in the summer.
Beat the Crowds: Everyone from the Obamas to Oprah visit the Vineyard in the summertime, which is exactly why you should go during the shoulder seasons of May and October when hotel prices drop considerably. October tends to be the relative sweet spot, with the luxury of all of the restaurants, shops, and bars still open minus the crowds.