Annapolis Holidays

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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
Annapolis showing street scenes and a city as well as a small group of people

Historic District

1 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.

Find hotels in Historic District

Top hotels in Annapolis

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,816 reviews)
"Excellent location for downtown and Acadamy access. Really enjoyed the history of the location and the displays. Staff was wonderful!"

Reviewed on 7 Aug 2025

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Historic Inns of Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is HK$1,217 per night from 17 Aug to 18 Aug
HK$1,217
HK$1,387 total
17 Aug - 18 Aug
includes taxes & fees
9.4/10 Exceptional! (1,000 reviews)
"This hotel is great. Good location accommodations are beautiful. The only thing they lack is a coffee maker in the room."

Reviewed on 7 Aug 2025

Graduate by Hilton Annapolis
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3 out of 5
2600 Housley Road, Annapolis, MD
Fully refundable
The price is HK$761 per night from 17 Aug to 18 Aug
HK$761
HK$867 total
17 Aug - 18 Aug
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"You all have some of the best staff ever. I liked the property so much that I’m planning my next trip to stay again already. My grandkids love the idea that we can just go downstairs to get breakfast and make your own waffles. Last but not least, the hot tub and swimming pool is on point."

Reviewed on 7 Aug 2025

Country Inn & Suites by Radisson, Annapolis, MD
See all 581 properties in Annapolis
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.

Popular places to visit

William Paca House

William Paca House

Learn about the life and explore the historic home of 18th-century lawyer and signer of the Declaration of Independence, William Paca.

William Paca House

Westfield Annapolis Mall

During your trip to Parole, you can do some window-shopping at Westfield Annapolis Mall. Amble around the area's waterfront or attend a sporting event.

Westfield Annapolis Mall

Maryland Hall for Creative Arts

Rich with history, Maryland Hall for Creative Arts is a cultural attraction worth visiting in Annapolis. Amble around the area's waterfront or attend a sporting event.

Maryland Hall for Creative Arts

What to do in Annapolis

Food Tour Plate

Historic Annapolis Food Tour

HK$628
per adult
Historic Annapolis Food Tour
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour

Annapolis: Historical Treasures of the City with Self-Guided Audio Tour

HK$77
per traveller
80% of travellers recommend
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour
Step into the shadows and discover the haunting tales of our city's past.

Haunted Annapolis: Ghosts of the Harbor & Old Town Tour

HK$204
per adult
100% of travellers recommend
Haunted Annapolis: Ghosts of the Harbor & Old Town Tour
See all activities in Annapolis

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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.