- Style: Classic
While it sits steps from East Hampton’s boutique and gallery-packed main drag, entering this six-room inn (there’s also a separate two-family carriage house) is a lot like stepping into a time machine. The picket-fenced, whitewashed home has functioned as a hotel since—you guessed it—1770. Alongside modern additions like the in-room iPad docks and flat screens, its beautiful Colonial flourishes—exposed wooden beams, antique fireplace—are perfectly intact. We go for the ever-reliable and delicious burgers at the on-site restaurant.