Annapolis Vacation Packages
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Your Annapolis Vacation
Book a custom vacation package to Annapolis and get ready to experience this fascinating city how you like. Consider spending time in the neighborhood of Historic District, which is good for history and tons more. If a sightseeing tour is part of the program during your trip to Annapolis, stop by leading attractions like U.S. Naval Academy, Maryland State House and William Paca House. Check out Expedia's wide range of travel options and book your ideal vacation to Annapolis now.
Top Annapolis Vacation Deals
Kellogg Conference Hotel at Gallaudet University
Reviewed on May 25, 2026
Rosewood Washington, D.C.
Reviewed on May 24, 2026
The Waypoint
Reviewed on May 18, 2026
Kimpton Banneker Hotel by IHG
Reviewed on May 23, 2026
Where to stay in Annapolis
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.
Annapolis Hotel Deals
DoubleTree by Hilton Hotel Annapolis
"Great for a clean quiet stay. The shuttle is a plus !"
Reviewed on May 25, 2026
Historic Inns of Annapolis
"We stayed for 5 days and experienced a rotation of Staff members while we were there. All of them were very pleasant and very helpful, which enhanced our stay. We stayed in the Robert Johnson Building and our room was in very good condition and very clean. We used Uber so we did not have a vehicle, ..."
Reviewed on May 24, 2026
Graduate by Hilton Annapolis
"The Graduate is an amazing hotel. My favorite part was the attentiveness of the staff, the nostalgic USNA decor, and the greeting of hot chocolate during an unexpected cold and rainy day in May!"
Reviewed on May 23, 2026
Discover the most popular places to visit in Annapolis
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.
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.
Chesapeake Bay Bridge
Attempt the nerve-racking drive across this long and notoriously scary bridge, which provides fabulous views of Chesapeake Bay for passengers.
What to do in Annapolis
Ashes and Apparitions of Annapolis Ghost Tour
