Oyster Harbor Vacations
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Where to stay in Oyster Harbor
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.
Oyster Harbor Hotel Deals
Cozy 3-bdrm home in Annapolis. Steps away from the beach/4.7 miles to downtown.
Lovely house, had everything we needed for a quick business trip.
Reviewed on 12 October 2025
DoubleTree by Hilton Hotel Annapolis
Clean and we moved to a quiet room as well
Reviewed on 8 January 2026
Graduate by Hilton Annapolis
Pleasant staff. Good location to walk to restaurants, shops.
Reviewed on 30 December 2025
Discover the most popular places to visit in Oyster Harbor
U.S. Naval Academy
Take a campus tour or just explore the area of U.S. Naval Academy, during your trip to Naval Academy. Wander the area's waterfront or simply enjoy one of its top-notch restaurants.
Chesapeake Bay Bridge
Find out about the history of Annapolis with a stop at Chesapeake Bay Bridge. Stroll along the area's waterfront, or simply savor its top-notch restaurants.
Sandy Point State Park
Enjoy a trip to Sandy Point State Park and popular activities like boating in Annapolis. Stroll along the area's waterfront, or simply savor its top-notch restaurants.