Gaze at sailboats cruising the harbor from inside the Inn at Perry Cabin (from $390). Its 78 rooms are outfitted with touches like wide, striped couches, brass desk-lamps, and old-fashioned standing mirrors, but request room 36 for a bit of history—it was once the master bedroom of a War of 1812 veteran, who had it built to resemble a ship’s cabin.
Step into a scene from Gone With the Wind at the Brampton Inn (from $179), a 19th-century plantation house near Chesterton. Seven rooms in the old mansion and six separate cottages all feature southern touches like flower prints and four-poster beds, while the Fairy Hill duplex suite offers a wood-burning fireplace in the sitting room and a whirlpool tub. In the evening, relax at the brandy honor bar in the little library on the first floor.
Pad around the original thick-planked wooden floors of the Kent Manor Inn (from $149), built in 1820. Of the 24 guest rooms, request one on the second floor for more space, ten- to twelve-foot ceilings, and wide balconies. Borrow one of the in-house bikes and pedal around the property—a 220-acre farm—or out to the six-mile Cross Island trail that loops through tranquil Terrapin Beach Park.