Annapolis Holidays

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Your Annapolis Holiday

Organising your next big escape is easy with an Annapolis holiday package. The neighbourhood of Historic District, which is good for history, makes a good starting point to discover the wonders of this unique city. Any trip to Annapolis needs a well-planned itinerary. Fill yours with major attractions such as U.S. Naval Academy, Maryland State House and William Paca House. A couple of quick clicks is all it takes to build the perfect Annapolis holiday on Expedia.

Our guide on where to stay in Annapolis

Find the best Annapolis areas and neighborhoods for the activities you enjoy most. Learn more about Annapolis
An aerial view of a coastal town with a prominent church, dense residential area, and a marina with boats.

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.

Find hotels in Historic District

Annapolis Holiday

Annapolis Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Baltimore Washington Intl. Thurgood Marshall Airport (BWI)
Population
39,500
Max Temp Winter
7ºC
Max Temp Summer
29ºC
Top Sights
Sandy Point State Park, Sandy Point Beach and Thanksgiving Farm Wines

Our pick of the best Annapolis Hotel Deals

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
The price is AU$231 per night from 20 July to 21 July
AU$231
20 July - 21 July
includes taxes & fees
9/10 Wonderful! (1,875 reviews)
"I loved the historic building- upgraded with 21stC amenities of course- like electricity and an elevator. Bed was very cozy. Bathroom window faced St. Mary's church and bedroom faced Capitol bldg. A short 2 block walk to a city owned parking garage, $24 for 24 hours. Not bad. And the restaurants ..."

Reviewed on 15 July 2026

Historic Inns of Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
The price is AU$185 per night from 2 Aug to 3 Aug
AU$185
2 Aug - 3 Aug
includes taxes & fees
DoubleTree by Hilton Hotel Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
Fully refundable
The price is AU$193 per night from 16 Aug to 17 Aug
AU$193
16 Aug - 17 Aug
includes taxes & fees
Crowne Plaza Annapolis by IHG
See all 554 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Stay near popular Annapolis attractions

A park with a walking path, picnic tables, and a large tree. In the background, there is a bridge over a body of water.

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.
See properties

What to do in Annapolis

Ashes and Apparitions of Annapolis Ghost Tour

Ashes and Apparitions of Annapolis Ghost Tour

AU$46
per adult
100% of travellers recommend
Ashes and Apparitions of Annapolis Ghost Tour
Historic Annapolis Food Tour

Historic Annapolis Food Tour

AU$116
per adult
Historic Annapolis Food Tour
Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl

Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl

AU$52
per adult
Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl
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.

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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.