Western Chesapeake Vacation Packages

Visit big cities such as Baltimore and Annapolis, charming towns and beautiful seaside parks in this region of Maryland.

Western Chesapeake is the unofficial region of Maryland west of the Chesapeake Bay. The region includes the city of Baltimore, Harford County, Baltimore County, Anne Arundel County, Calvert County and Saint Mary's County. Enjoy the cultural offerings of the region’s metropolises and the wild beauty of the Chesapeake Bay.

As the largest city in Maryland, Baltimore is Western Chesapeake’s cultural and commercial hub. See works by Matisse, Picasso and other renowned artists at the Baltimore Museum of Art or enjoy outdoor shopping at Broadway Market. Don't miss Fort McHenry National Monument, where Francis Scott Key saw the flying American flag that inspired him to write the national anthem of the United States, The Star-Spangled Banner.

Visit the picturesque port town of Annapolis, the capital city of Maryland. The Annapolis Maritime Museum gives visitors insight into the maritime history of Chesapeake Bay. Go crabbing off the museum's piers or explore the bay area by kayak. Watch future officers conduct a perfectly synchronized noon formation at the United States Naval Academy, which has a campus in the heart of the city. 

Stroll some of the miles of shoreline in Western Chesapeake. Just outside Baltimore, North Point State Park is a serene oceanfront park. Consisting of preserved and farmed land, it is one of the finest examples of tidal marshland in the Chesapeake area. In the southern part of the region, enjoy miles of hiking, biking and equestrian trails at Greenwell State Park. At the head of the Patuxent River, Merkle Wildlife Sanctuary is the resting grounds of thousands of migrating Canadian geese each year.

Rent a car to explore everything Western Chesapeake has to offer, from small oceanfront villages and national parks to large cities. Temperatures in Western Chesapeake are rarely extreme but you can expect hot summers and chilly winters. Summer is peak visitor season. 

Top Hotels

See all Western Chesapeake Shore hotels
1.0 out of 5.0
1.5 out of 5.0
2.0 out of 5.0
2.5 out of 5.0
3.0 out of 5.0
3.5 out of 5.0
4.0 out of 5.0
4.5 out of 5.0
5.0 out of 5.0
Most popular package deals found by our travelers
Most popular package deals found by [originCity] travelers

Western Chesapeake Shore Vacation Package Deals

See all Western Chesapeake Shore packages

Top Deals on Flights

See all Western Chesapeake Shore flights

Book your Western Chesapeake Shore Vacation Package