St. Michaels, Maryland

Set beside the historic Chesapeake Bay, St. Michaels, Maryland, is home to Inspirato’s Chesapeake Estate, a quintessential waterfront residence with a private pier, sprawling yard, and large, heated swimming pool. With an expansive great room and gourmet kitchen, the home is perfect for the whole family to relax together after days filled with activities like fishing, swimming, and yard games.

For couples or individuals, the Inn at Perry Cabin offers elegant, classically furnished accommodations set in a colonial-style, 19th-century manor.

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