Annapolis Vacations
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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 Ballet Theater of Maryland and Spa Creek.
Hillsmere
If you're spending some time in Hillsmere, Maryland Quiet Waters Park and Great Frogs Winery are top sights worth seeing.
Admiral Heights
Admiral Heights might not have many top sights, but Navy-Marine Corps Memorial Stadium and Maryland Hall for Creative Arts are two attractions nearby that you can check out.
Find the Best Annapolis Vacation Packages
Annapolis Hotel Deals
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
₩112,412
₩128,150 total
Sep 27 - Sep 28
includes taxes & fees
8.8/10 Excellent! (1,196 reviews)
"We were comfortable, very comfortable actually and this hotel had everything we needed to get our son off to college."
Reviewed on Sep 23, 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
₩146,078
₩213,511 total
Oct 12 - Oct 13
includes taxes & fees
9/10 Wonderful! (2,020 reviews)
"Superb location. Very tastefully treated. My only suggestions would be to provide more information regarding parking and a technology update in the rooms would be helpful. Plugs for charging was difficult as extensions and adapters were not reliable. High definition TV should be added as well. For ..."
Reviewed on Sep 22, 2026
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
₩151,113
₩172,269 total
Sep 27 - Sep 28
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
Sandy Point State Park
8.6/10 (221 reviews)
Sandy Point State Park offers pristine Chesapeake Bay beachfront beneath the towering Bay Bridge. Visitors can launch boats, fish for striped bass, or attend the renowned Maryland Seafood Festival.
Chesapeake Bay Bridge
8.8/10 (1,066 reviews)
This 4.3-mile engineering marvel connects Maryland's shores while offering spectacular panoramic bay views. Drive across at sunrise to witness the Chesapeake's shimmering waters dotted with sailboats below.
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.
Navy-Marine Corps Memorial Stadium
9.2/10 (287 reviews)
Home to the Navy Midshipmen teams, this stadium honors naval service members with its impressive Memorial Plaza. Catch the vibrant atmosphere of a fall football game or the annual Annapolis Crab Feast in August.
Westfield Annapolis Mall
8.8/10 (394 reviews)
Westfield Annapolis offers over 200 stores, from luxury boutiques to popular department stores. Explore high-end fashion, dine at diverse restaurants, or catch a film at the state-of-the-art theater.
Annapolis Mall Shopping Center
9.0/10 (23 reviews)
Annapolis Mall offers over 140 stores including Macy's and Nordstrom in a spacious, well-maintained environment. Visit weekday mornings for a relaxed shopping experience, then catch a film at the 11-screen AMC theater.
Maryland Renaissance Festival
10.0/10 (1 review)
Step back in time at this sprawling 16th-century English village recreation with over 200 performers. Watch jousting tournaments, sample period foods like turkey legs, and browse 140 artisan craft shops.
Sandy Point Beach
9.6/10 (10 reviews)
Sandy Point State Park features a mile-long beach with Bay Bridge views on the Chesapeake. Enjoy swimming in calm waters, launch a boat from the marina, or experience the September Seafood Festival.
Frequently asked questions
How much does an Annapolis vacation package cost?
You can snap up a vacation package to this popular destination on Expedia. However, how much your vacation to Annapolis costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Annapolis?
You're likely to find lower prices and greater availability in January, February and March. Take a look at our cheap Annapolis vacation packages and you could land some excellent off-season deals.
How many days is enough for Annapolis?
Annapolis vacations come in various shapes and sizes, but to get a real feel for this destination, we think 2 days is a good ballpark. In this timeframe, you can visit major attractions like Bay Ridge Beach and Annapolis Bowl along with lesser-known gems. Don't forget to explore neighborhoods such as Parole and Historic District either. If you're smart with your time, you can even schedule a day trip from Annapolis too.
Is it worth booking a vacation package to Annapolis?
Popular for its history, culture and watersports, an Annapolis vacation has something for everyone. Be sure to check out main sights like Annapolis City Dock and Westfield Annapolis Mall, and consider renting some wheels for day trips to explore even more.
How to find the best Annapolis package deals?
Finding a cheap Annapolis package deal is a breeze with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget, add a few filters and browse what's available. You can tailor your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Annapolis package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book an Annapolis vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll generally land a better deal than booking each component separately. And you'll still enjoy the flexibility to create a tailored Annapolis vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Annapolis?
If you're considering a spontaneous Annapolis adventure, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can find terrific deals on your flights and hotels by booking well in advance.
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
