Annapolis Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 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
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
Lord Baltimore Hotel
Reviewed on Feb 4, 2026
Pendry Baltimore
Reviewed on Feb 6, 2026
Embassy Suites by Hilton Baltimore at BWI Airport
Reviewed on Feb 3, 2026
The Inn at Henderson's Wharf, an Ascend Collection Hotel
Reviewed on Dec 21, 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.
Annapolis Hotel Deals
Historic Inns of Annapolis
Everything about this beautiful historic hotel was beautiful and perfect—I can’t wait to come back!
Reviewed on Jan 31, 2026
Graduate by Hilton Annapolis
The room was very spacious. Staff were nice. Amenities were excellent. Good location for our stay.
Reviewed on Feb 5, 2026
Country Inn & Suites by Radisson, Annapolis, MD
The room was nice. The staff were fine. Location good. Pool nice. The breakfast was poor quality and location.
Reviewed on Jan 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.
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
Ashes and Apparitions of Annapolis Ghost Tour
