Annapolis Vacations from $210

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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.

The Latest Annapolis vacation packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Hotel Laurel
Canopy by Hilton Baltimore Harbor Point
Element Arundel Mills BWI Airport
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
The Inn at Henderson's Wharf, Ascend Hotel Collection
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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

Discover the most popular places to visit in Annapolis

What to do in Annapolis

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
$143 nightly
The price is $163 total per night from Jul 20 to Jul 21
$163 total
Jul 20 - Jul 21
Total includes taxes and fees
8.8/10 Excellent! (1,795 reviews)
THE INN PLACE TO BE
"A quick overnight to celebrate July 4th in Annapolis. The Inn was perfectly placed to take it all in. Easy valet parking; warm, welcoming front desk staff; and, a clean, comfy, well-appointed room made for a memorable holiday."

Reviewed on Jul 5, 2025

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
$155 nightly
The price is $177 total per night from Aug 3 to Aug 4
$177 total
Aug 3 - Aug 4
Total includes taxes and fees
9.4/10 Exceptional! (1,008 reviews)
"Very nice property the rooms were great as was he service!"

Reviewed on Jul 7, 2025

Graduate by Hilton 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
$102 nightly
The price is $116 total per night from Aug 3 to Aug 4
$116 total
Aug 3 - Aug 4
Total includes taxes and fees
8.4/10 Very Good! (1,001 reviews)
"Staff was very nice and professional!"

Reviewed on Jul 10, 2025

DoubleTree by Hilton Hotel 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.

Find the Best Annapolis Vacation Packages

Annapolis Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Baltimore Washington Intl. Thurgood Marshall Airport (BWI)
Population
39,500
Max Temp Winter
45ºF
Max Temp Summer
85ºF
Top Sights
Sandy Point State Park, Sandy Point Beach and Matapeake State Park

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Frequently asked questions

How much does an Annapolis vacation package cost?
You can snap up a vacation package to this popular destination from $210 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?
January, October and December are the best times to search for cheap Annapolis vacation packages. Opting to travel in quieter months means you can typically find lower prices on accommodations and flights.
How many days is enough for Annapolis?
With around 2 days, you'll have enough time to experience popular neighborhoods such as Parole and Historic District during your Annapolis vacation. Be sure to also add Bay Ridge Beach and Annapolis Bowl to your must-do list. Looking for more adventures? Consider exploring outside of Annapolis on day trips and tours.
Is it worth booking a vacation package to Annapolis?
Well known for its culture, watersports and festivals, an Annapolis vacation is a hit with all kinds of travelers. Be sure to check out leading sights like William Paca House and Navy-Marine Corps Memorial Stadium, and consider renting a car for day trips to experience 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?

  1. Pick the best time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to travel to Annapolis.
  2. Calculate your budget: Ensure you have enough money to cover everything from transportation and dining out to flights and activities. Your accommodations will likely be the biggest expense during your trip to Annapolis.
  3. Explore Annapolis using our trip planning tool: Gain insights into the top attractions and best hotels for your trip to Annapolis. You can also save your favorite places, collaborate with family and friends and manage your plans in one place.
  4. Decide how long to go away for: Now that you're more familiar with Annapolis, you can work out the right length of your break. Pull together a rough plan and allocate enough time to cover everything you want to see.
  5. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to choose an Annapolis vacation package that brings all your bookings together.
  6. Book any activities or excursions: Here's the fun part --- locking in everything you want to see and do. Browse some of the incredible things to do in Annapolis and reserve your tickets in advance to save time (and maybe some cash too!).

Does Expedia offer Book Now, Pay Later Annapolis vacation packages?
Set off on your dream getaway to Annapolis with help from our Book Now, Pay Later vacations. No need to save up or wait for your next paycheck --- we've partnered with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans let you split the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily budget for your trip and snap up bargains while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.