Eastern Shore Maryland USA Vacation Rentals by Owner.Many rentals offer scenic views of the Chesapeake Bay and its tributaries, providing a tranquil setting for your stay.Some properties include private pools and hot tubs, enhancing your relaxation experience. Many rentals offer scenic views of the Chesapeake Bay and its tributaries, providing a tranquil setting for your stay.A charming waterfront town, St. Michaels offers a variety of vacation rentals, including historic homes and modern cottages. Eastern Shore Maryland USA Vacation Rentals by Owner.Eastern Shore Maryland USA Vacation Rentals by Owner.