Nicknamed “the un-Hamptons,” Shelter Island is a peaceful island community situated on the eastern end of Long Island. Shelter Island is only accessible by ferry and sits just five minutes from its bustling neighbor, the Hamptons. Adorned with old-fashioned buildings along tree-lined streets, Shelter Island exudes small-town charm and tranquil luxury in equal measure.

The community’s secluded feel is a part of its allure, despite being within close reach of wine country and the Hamptons. Shelter Island is also roughly a two-hour drive from New York City. Shelter Island’s rental homes generally offer quick access to the community’s many beaches as well as the locally owned shops and restaurants that line Ferry Road.