
Annapolis Vacations from ¥389,425
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Find the right fit
Rest easy
The Latest Annapolis Vacation Packages

Staybridge Suites Baltimore - Inner Harbor by IHG
Reviewed on Aug 28, 2025

Graduate by Hilton Annapolis
Reviewed on Aug 30, 2025

Canopy by Hilton Baltimore Harbor Point
Reviewed on Aug 28, 2025

Marriott Owings Mills Metro Centre
Reviewed on Aug 24, 2025

Hotel Indigo Baltimore Downtown by IHG
Reviewed on Aug 30, 2025
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

Historic Inns of Annapolis
Reviewed on Aug 29, 2025

The Westin Annapolis

Country Inn & Suites by Radisson, Annapolis, MD
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.

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.
What to do in Annapolis

Haunted Annapolis: Ghosts of the Harbor & Old Town Tour
