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Set beside the historic Chesapeake Bay, St. Michaels, Maryland, is a charming seaside town with a laid-back coastal feel and plenty of history to explore. Stay with Inspirato at Mulberry, an expansive, six-bedroom home steps from Grace Creek with its own private dock. Enjoy ample outdoor space, including a pool, outdoor kitchen, and fire pit. Or, enjoy colonial-style accommodations at the Inn at Perry Cabin, with an on-site sailing academy and 26 acres of lush gardens.