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The Latest Winchester-on-the-Severn Vacation Packages


The William Fell Baltimore, Tapestry Collection by Hilton
Reviewed on Aug 8, 2025


Renaissance Baltimore Harborplace Hotel
Reviewed on Aug 6, 2025
Where to stay in Winchester-on-the-Severn

Historic District
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.
Winchester-on-the-Severn Hotel Deals

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport
Reviewed on Aug 7, 2025

Holiday Inn Baltimore BWI Airport by IHG
Reviewed on Aug 4, 2025

Historic Inns of Annapolis
Reviewed on Aug 4, 2025
Frequently asked questions
Discover the most popular places to visit in Winchester-on-the-Severn

U.S. Naval Academy
See where future generations of Navy and Marine Corps officers are trained at this historic federal service academy within a former fort in Annapolis harbor.

Chesapeake Bay Bridge
Attempt the nerve-racking drive across this long and notoriously scary bridge, which provides fabulous views of Chesapeake Bay for passengers.

Sandy Point State Park
Sunbathe on the beach, enjoy unrivaled views of the Chesapeake Bay Bridge and go hiking, swimming, fishing and boating in this vast park.
Things to do

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
