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Annapolis Vacations from $236

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The Latest Annapolis Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Courtyard
    Oct 16 - Oct 18

    The Knight Center at Washington University + Flight

    St. Louis
    2 nights
    2.5 star property
    9.4/10 - Exceptional (638 reviews)
    "Very nice location. Quiet. University grounds are beautiful."
    Reviewed July 26, 2026
    Roundtrip • Atlanta (ATL) - St. Louis (STL)
    ATL - STL • Nonstop STL - ATL • Nonstop
    Save 100% on your flight
    $322
    $236
    per traveler
    found 23 hours ago
    The Knight Center at Washington University
  • Property entrance
    Sep 17 - Sep 22

    The Wildwood Hotel + Flight

    Wildwood
    5 nights
    3.5 star property
    9.2/10 - Wonderful (1,668 reviews)
    Roundtrip • Atlanta (ATL) - St. Louis (STL)
    ATL - STL • Nonstop STL - ATL • Nonstop
    Save 100% on your flight
    $947
    $523
    per traveler
    found 1 day ago
    The Wildwood Hotel
  • House | Private kitchen
    Sep 17 - Sep 22

    Remodeled and Inviting Free EV + Flight

    Fenton
    5 nights
    2.0 star property
    10/10 - Exceptional (1 review)
    "The property was excellent, and the home was very warm and welcoming."
    Reviewed June 25, 2026
    Roundtrip • Atlanta (ATL) - St. Louis (STL)
    ATL - STL • Nonstop STL - ATL • Nonstop
    Save 100% on your flight
    $982
    $625
    per traveler
    found 1 day ago
    Remodeled and Inviting Free EV
  • Poolside bar
    Aug 25 - Aug 31

    Lodge Of Four Seasons Golf Resort, Marina & Spa + Flight

    Lake Ozark
    6 nights
    4.0 star property
    7.4/10 - Good (1,251 reviews)
    Roundtrip • New York (NYC) - St. Louis (STL)
    LGA - STL • Nonstop STL - EWR • 1 stop
    Save 100% on your flight
    $842
    $551
    per traveler
    found 7 hours ago
    Lodge Of Four Seasons Golf Resort, Marina & Spa
  • Gastropub
    Sep 17 - Sep 22

    The Cheshire + Flight

    Richmond Heights
    5 nights
    4.0 star property
    8.8/10 - Excellent (1,004 reviews)
    "The boutique hotel was a very neat experience. The staff was very helpful. It was a central location for the things we wanted to do while in St. Louis."
    Reviewed July 26, 2026
    Roundtrip • Atlanta (ATL) - St. Louis (STL)
    ATL - STL • Nonstop STL - ATL • Nonstop
    Save 100% on your flight
    $903
    $662
    per traveler
    found 1 day ago
    The Cheshire

Annapolis Hotel Deals

Dining

Black River Motel and Restaurant

Black River Motel and Restaurant
2.0 star property
10.2 mi from Annapolis
8.6 out of 10, Excellent, (43 reviews)
"Staff was very helpful and friendly"
$129 nightly
The price is $136
Jul 27 - Jul 28
Total with taxes and fees
Black River Motel and Restaurant
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.
See all properties in Annapolis

Frequently Asked Questions

How much does an Annapolis vacation package cost?

You can grab a vacation package to this top destination from $236 on Expedia. However, how much your vacation to Annapolis costs will depend on factors like the season, length of stay and hotel choice.

What are the cheapest months to go to Annapolis?

You can typically find lower prices and greater availability in January, February and November. Explore our cheap Annapolis vacation packages and you could get some great off-season discounts.

How many days is enough for Annapolis?

The ideal length of your Annapolis vacation depends on what you'd like to see. Usually, a few days to a week will give you plenty of time to tick off all the top sights and discover some hidden treasures along the way.

How to find the best Annapolis package deals?

Use Expedia's filters to help you find some unbeatable Annapolis package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or look for Annapolis package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.

Is it cheaper to book an Annapolis vacation as a package?

Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component separately. And you'll still get the flexibility to create a customized Annapolis vacation by choosing your favorite airline, accommodation type and car class.

When to book a vacation package to Annapolis?

If you've got your Annapolis vacation dates confirmed, book as soon as you can to snap up some awesome deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are ideal for traveling on a whim.

Does Expedia offer Book Now, Pay Later Annapolis vacation packages?

Your Annapolis trip should be a relaxing escape from your busy life, not a source of money worries. So to give you that extra flexibility, we've joined up with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.