Annapolis Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ₩234,741 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Find the Best Annapolis Vacation Packages
Annapolis Hotel Deals
Graduate by Hilton Annapolis
The toilet ran every few minutes. Some of the carpet as we entered the room was worn away.
Reviewed on Mar 22, 2026
Crowne Plaza Annapolis by IHG
Very close to several restaurants and the mall is close as well. Golf course is within 15 mins
Reviewed on Mar 23, 2026
Historic Inns of Annapolis
Great location
Reviewed on Mar 21, 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.
Chesapeake Bay Bridge
Attempt the nerve-racking drive across this long and notoriously scary bridge, which provides fabulous views of Chesapeake Bay for passengers.
Maryland Quiet Waters Park
Stroll along miles of trails through grassy parkland, hardwood forests and riverfront promenades and check out the visitor center at this pretty park.
