Hob Knob

Set back from the hubbub of downtown Edgartown, this eco-friendly, 17-room manse is quiet, unpretentious, and posh. (JFK himself once stayed here after an exhausting regatta.) Eat your made-to-order breakfast, then ride one of the cruiser bikes to the beach or to the island’s farm institute to gather fresh eggs. And after that? Just linger in the Garden Room till it’s time for cookies and tea.