Annapolis Holidays
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- Better togetherSave up to S$1,300 when you book a flight and hotel together*
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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
While visiting Historic District, you might make a stop by sights like Maryland State House and William Paca House.
Eastport
While visiting Eastport, you might make a stop by sights like Annapolis Maritime Museum and Annapolis Harbor.
Murray Hill
If you're spending some time in Murray Hill, Ballet Theater of Maryland and Spa Creek are top sights worth seeing.
Hillsmere
While visiting Hillsmere, you might make a stop by sights like Maryland Quiet Waters Park and Great Frogs Winery.
Cape Saint Claire
While visiting Cape Saint Claire, you might make a stop by sights like Northern Chesapeake Bay and Chesapeake Bay.
Top hotels in Annapolis
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
S$141
30 Aug - 31 Aug
includes taxes & fees
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
S$177
27 Aug - 28 Aug
includes taxes & fees
9/10 Wonderful! (1,961 reviews)
"A great property in a great location . The people we interacted with were friendly and helpful. I highly recommend Historic Inn in Annapolis"
Reviewed on 20 Aug, 2026
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
Fully refundable
S$159
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (1,010 reviews)
"Rooms where clean, staff was nice"
Reviewed on 21 Aug, 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
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.
William Paca House
8.6/10 (24 reviews)
Learn about the life and explore the historic home of 18th-century lawyer and signer of the Declaration of Independence, William Paca.
Navy-Marine Corps Memorial Stadium
9.2/10 (287 reviews)
Home to the Navy Midshipmen teams, this stadium honours 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.
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.
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 theatre.
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.
What to do in Annapolis
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour
S$12
per traveller
80% of travellers recommend
Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl
S$37
per adult
Frequently asked questions
How much does an Annapolis holiday package cost?
You can snap up a holiday package to this popular destination on Expedia. However, how much your holiday 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 holiday packages and you could land some excellent off-season deals.
How many days is enough for Annapolis?
Annapolis holidays 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 neighbourhoods 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 holiday package to Annapolis?
Popular for its history, culture and watersports, an Annapolis holiday 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 holiday as a package?
Expedia holiday 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 holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday 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, favourite 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 holiday package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
