
Annapolis Vacations from ₩3,135,920
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ₩1,660,000 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
The Latest Annapolis Vacation Packages



Eurostars Saint Gregory Dupont Circle Georgetown
Reviewed on Aug 7, 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.

Eastport
While visiting Eastport, you might make a stop by sights like Annapolis Maritime Museum and Annapolis Harbor.

Murray Hill
While visiting Murray Hill, you might make a stop by sights like Spa Creek and Ballet Theater of Maryland.

Hillsmere
If you're spending some time in Hillsmere, Maryland Quiet Waters Park and Great Frogs Winery are top sights worth seeing.

Cape Saint Claire
Boasting three marinas, multiple parks and beaches, Cape St. Claire offers a shopping center and various churches, with easy access to Annapolis and the Chesapeake Bay Bridge via U.S. Route 50.
Find the Best Annapolis Vacation Packages
Annapolis Hotel Deals

DoubleTree by Hilton Hotel Annapolis
"Great staff"
Reviewed on Aug 7, 2026

Historic Inns of Annapolis
"Nice very well location"
Reviewed on Aug 6, 2026

Crowne Plaza Annapolis by IHG
"Nice stay. No complaints."
Reviewed on Aug 7, 2026
Stay near popular Annapolis attractions

Sandy Point State Park

Chesapeake Bay Bridge

Maryland State House

William Paca House
Navy-Marine Corps Memorial Stadium
Westfield Annapolis Mall
Sandy Point Beach
Maryland Renaissance Festival
Frequently asked questions
How much does an Annapolis vacation package cost?
What are the cheapest months to go to Annapolis?
How many days is enough for Annapolis?
Is it worth booking a vacation package to Annapolis?
How to find the best Annapolis package deals?
Is it cheaper to book an Annapolis vacation as a package?
When to book a vacation package to Annapolis?
How to plan a trip to Annapolis?
- Pick the perfect time to travel: Your schedule, favorite season and the type of weather you like can all influence your decision on when to visit Annapolis.
- Set a budget: Factor in costs like flights, food and transportation when working out how much to put aside for your trip to Annapolis. Then, choose a property that matches your budget, whether that's a wallet-friendly option or a more luxurious retreat.
- Set the duration of your trip: Start by making a list of all the sights and activities you'd like to get to in Annapolis. Then, estimate how long you'll need for each, as well as any travel time.
- Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to pick an Annapolis vacation package that brings all your bookings together.

