Winchester-on-the-Severn Vacations from $307

Discover a well-preserved historic district with elements of the original town plan, featuring landmarks like the Maryland State House, St. Ann's Church, and Paca House and Gardens. The neighborhood features prestigious educational institutions like St. John's College and the U.S. Naval Academy.

While visiting Eastport, you might make a stop by sights like Annapolis Maritime Museum and Annapolis Harbor.

While visiting Murray Hill, you might make a stop by sights like Ballet Theater of Maryland and Spa Creek.

Boasting three marinas, multiple parks and beaches, Cape St. Claire offers a shopping center and various churches, with easy access to Annapolis and the Chesapeake Bay Bridge via U.S. Route 50.

If you're spending some time in Hillsmere, Maryland Quiet Waters Park and Great Frogs Winery are top sights worth seeing.