Annapolis Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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
Price found within the past 48 hours. Click for updated prices.
The Quincy, an Ascend Collection Hotel
Downtown Washington D.C.
CA $794
per person
Dec 7 - Dec 10
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9.2/10 Wonderful! (1,137 reviews)
A great size room which was clean and comfortable. Great location for sightseeing and a good variety of restaurants within walking distance. Staff were friendly and helpful.
Reviewed on Oct 15, 2026
The Potomac Hotel, Autograph Collection
Southwest
CA $3,729
per person
Nov 16 - Nov 21
found 1 hour ago
Roundtrip flight included
Edmonton (YEG) to Baltimore (BWI)
9.4/10 Exceptional! (1,089 reviews)
Clean, convenient to many walkable places and easy to get a taxi or Uber if needed.
Reviewed on Oct 13, 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
Graduate by Hilton Annapolis
126 West St Annapolis MD
Fully refundableReserve now, pay when you stay
CA $208
CA $237 total
Oct 26 - Oct 27
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
"Good"
Reviewed on Oct 15, 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
CA $150
CA $172 total
Oct 18 - Oct 19
includes taxes & fees
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
Fully refundable
CA $156
CA $178 total
Oct 25 - Oct 26
includes taxes & fees
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.
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.
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.
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.
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.
Maryland Renaissance Festival
10.0/10 (1 review)
Have a fun-filled day with the family at Maryland Renaissance Festival 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: Annapolis Harbor and U.S. Naval Academy Cruise
CA $48
per adult
90% of travellers recommend
Annapolis Harbor and U.S. Naval Academy Cruise
CA $48
per adult
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
CA $42
per adult
Frequently asked questions
How much does an Annapolis vacation package cost?
You'll find cheap prices from CA $794 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.
