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
Price found within the past 48 hours. Click for updated prices.
Furnished Apartments
Ashton Heights
CA $824
per person
Oct 14 - Oct 17
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9/10 Wonderful! (4 reviews)
Location is excellent. Walking distance to pretty much everything you need. Space was very comfortable, clean, and the bed was excellent for sleeping. Lots of light and windows.
Host was helpful and able to accommodate my schedule needs too.
Reviewed on Apr 1, 2025
Hotel Burg
Leesburg's Old and Historic District
CA $1,862
per person
Sep 9 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
9.6/10 Exceptional! (100 reviews)
Excellent service and hospitality. Beautiful and clean. Would come back here many times. Friendly and professional staff. It was a great experience.
Reviewed on Aug 4, 2026
Where to stay in Annapolis
Find the best Annapolis areas and neighborhoods for the activities you enjoy most. Learn more about Annapolis
Historic District
2 out of top 10 points of interest in this area
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.
Ready to book your vacation to Annapolis?
Annapolis Hotel Deals
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
CA $137
CA $156 total
Aug 30 - Aug 31
includes taxes & fees
8.8/10 Excellent! (1,081 reviews)
"👍"
Reviewed on Aug 6, 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
CA $129
CA $194 total
Aug 25 - Aug 26
includes taxes & fees
9/10 Wonderful! (1,928 reviews)
"Nice very well location"
Reviewed on Aug 6, 2026
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
Fully refundable
CA $165
CA $188 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (1,012 reviews)
"This was an amazing stay! My room got serviced daily while I was out exploring and they kept everything nice and clean! The breakfast add on was so worth it so if you have the option to definitely add it! I had an amazing time and can’t wait to stay again!"
Reviewed on Aug 3, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Annapolis attractions
U.S. Naval Academy
9.4/10 (1,474 reviews)
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
8.6/10 (221 reviews)
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
8.8/10 (1,066 reviews)
Attempt the nerve-racking drive across this long and notoriously scary bridge, which provides fabulous views of Chesapeake Bay for passengers.
Maryland State House
9.0/10 (433 reviews)
Appreciate the superb architecture and fascinating history of America’s first peacetime capitol and the oldest state capitol still in legislative use.
Annapolis City Dock
9.4/10 (1,099 reviews)
You can search for that perfect souvenir at Annapolis City Dock during your visit to Annapolis. Stroll along the area's waterfront, or simply savor its top-notch restaurants.
Navy-Marine Corps Memorial Stadium
9.2/10 (287 reviews)
Catch an event at Navy-Marine Corps Memorial Stadium during your trip to Annapolis. Stroll along the waterfront or visit the shops in the area.
Westfield Annapolis Mall
8.8/10 (394 reviews)
During your trip to Parole, you can enjoy retail therapy at Westfield Annapolis Mall. Amble around the area's waterfront or attend a sporting event.
Sandy Point Beach
9.6/10 (10 reviews)
Why not spend a lazy afternoon at Sandy Point Beach during your trip to Annapolis? Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
What to do in Annapolis
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour
CA $14
per traveller
80% of travellers recommend
Frequently asked questions
How much does an Annapolis vacation package cost?
You'll find cheap prices from CA $688 on Expedia for your Annapolis escape. However, factors like the length of stay, hotel choice and season will influence how much your vacation to Annapolis costs.
What are the cheapest months to go to Annapolis?
You can typically find lower rates and greater availability in January, February and March. Browse our cheap Annapolis vacation packages and you could land some great off-season discounts.
How many days is enough for Annapolis?
To get the most out of an Annapolis vacation, we suggest booking for 2 days. Split your time between discovering Annapolis City Dock, Westfield Annapolis Mall and other well-known attractions, as well as experiencing neighbourhoods like Parole and Historic District. If you've got some time to spare, include a day trip or tour in your Annapolis vacation itinerary.
Is it worth booking a vacation package to Annapolis?
Whether you want to visit key attractions such as Annapolis City Dock and Westfield Annapolis Mall on your Annapolis vacation, or coming for its great history, culture and watersports, there's something for everyone here. With so much to see and do, you'll soon find out why so many visitors think Annapolis is a good vacation destination.
How to find the best Annapolis package deals?
Landing a cheap Annapolis package deal is a breeze with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget, add a few filters and see what's available. You can fine-tune your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most economical Annapolis package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book an Annapolis vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and hotels separately. Better still, you can tailor your Annapolis getaway to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Annapolis?
Enjoy incredible bargains by booking your flights early with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment Annapolis adventure.
How to plan a trip to Annapolis?
- Choose when to get away: Check your calendar and get your bags packed. Your preferred season and the type of activities on offer will also help you decide when to vacation in Annapolis.
- Budget wisely: Besides the price of your hotel, you'll need to consider other expenses too. These include flights, transportation and food. Also, set aside a little extra for unexpected costs that may arise during your trip to Annapolis.
- Decide how long to go for: Now that you're up to speed on Annapolis, you can figure out the right length of your vacation. Pull together a draft plan and give yourself enough time to cover everything you want to do.
- Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a customized Annapolis vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
