Annapolis Vacation Packages

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Your Annapolis Vacation

Pick a Annapolis vacation package and focus on what counts — having some fun. No more planning headaches, just a lot more free time to uncover what's special about this lively city, such as its rich history and coastal scenery. Fill your days with tours of K Bridge Recreation Area, Crane Lake Recreation Area and Walnut Hollow Lake, some of the attractions you should see during your trip to Annapolis. A couple of quick clicks is all it takes to build a customized Annapolis vacation on Expedia.

Top Annapolis vacation deals

Price found within the past 48 hours. Click for updated prices.
  • A reception desk with a large number '6' sign, a framed certificate, and a blue informational sign.
    Jan 23 - Jan 28

    Motel 6 Rolla, MO + Flight

    Rolla
    5 nights
    2.0 star property
    6.6/10 - (293 reviews)
    "I stayed there last night. The room was clean, the property was clean. My only issue was that I was asked to wait 15 minutes prior to entering tje room so they could make sure it was clean. I checked in late, after 10 pm so I think they should've known if the room was clean. I slept really good and the bed was comfortable. No issues with anything else."
    Reviewed November 6, 2026
    Roundtrip • Toronto (YYZ) - St. Louis (STL)
    YYZ - STL • Nonstop STL - YYZ • 1 stop
    CA $1,123
    CA $1,021
    per traveller
    found 1 day ago
    Motel 6 Rolla, MO
  • A hotel with a prominent tower, a fountain in the courtyard, and a well-maintained garden.
    Dec 18 - Dec 20

    The Wildwood Hotel + Flight

    Wildwood
    2 nights
    3.5 star property
    9.2/10 - Wonderful (1,677 reviews)
    Roundtrip • Calgary (YYC) - St. Louis (STL)
    YYC - STL • 1 stop STL - YYC • 1 stop
    CA $1,344
    CA $1,062
    per traveller
    found 1 day ago
    The Wildwood Hotel
  • A covered outdoor seating area with red rocking chairs and a fire pit.
    Jan 23 - Jan 28

    Hermann Grain Bins BNB + Flight

    Hermann
    5 nights
    2.0 star property
    7.4/10 - Good (3 reviews)
    "Our stay at the Grain Bins was excellent! The spaces were exactly as described! Everything was very clean and well appointed. Communication was great. We especially enjoyed relaxing around the fire pit. Homemade breakfast each morning was such a nice touch! Added bonus: The Hermann trolley was able to pick us up and drop us back off at the end of the day. Highly recommend staying at the Hermann Grain Bins and hope to stay again in the future!"
    Reviewed October 30, 2026
    Roundtrip • Toronto (YYZ) - St. Louis (STL)
    YYZ - STL • Nonstop STL - YYZ • 1 stop
    CA $2,771
    CA $2,359
    per traveller
    found 1 day ago
    Hermann Grain Bins BNB
  • A Comfort Inn hotel with a modern design, featuring a covered entrance and a clear sky in the background.
    Jan 23 - Jan 28

    Comfort Inn Sullivan + Flight

    Sullivan
    5 nights
    2.5 star property
    8.6/10 - Excellent (959 reviews)
    "Great location"
    Reviewed November 5, 2026
    Roundtrip • Toronto (YYZ) - St. Louis (STL)
    YYZ - STL • Nonstop STL - YYZ • 1 stop
    CA $1,320
    CA $1,215
    per traveller
    found 1 day ago
    Comfort Inn Sullivan
  • A pool area with a hot tub, seating, and a changing room.
    Jan 23 - Jan 28

    Holiday Inn Express Hotel & Suites Rolla - U of Missouri S&T by IHG + Flight

    Rolla
    5 nights
    2.5 star property
    8.8/10 - Excellent (970 reviews)
    "Elevator has been out of service for 2 weeks! No notice by Expedia of this"
    Reviewed October 31, 2026
    Roundtrip • Toronto (YYZ) - St. Louis (STL)
    YYZ - STL • Nonstop STL - YYZ • 1 stop
    CA $1,342
    CA $1,261
    per traveller
    found 1 day ago
    Holiday Inn Express Hotel & Suites Rolla - U of Missouri S&T by IHG

Discover the most popular places to visit in Annapolis

K Bridge Recreation Area

9.6/10 (4 reviews)
Explore the great outdoors at K Bridge Recreation Area, a lovely green space in Annapolis. While you're in the area, stroll along the riverfront.
See properties

Annapolis Hotel Deals

A narrow corridor with a bar area on the right, featuring a counter and hanging lights.

Black River Motel and Restaurant

Black River Motel and Restaurant
2.0 star property
16.4 km from Annapolis
8.6 out of 10, Excellent, (48 reviews)
"Shower didn’t have much pressure at all After hiking all day would have been nice to have a good working shower with water pressure"
The price is CA $182
CA $193 total
includes taxes & fees
Nov 12 - Nov 13
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?

Offering excellent value package deals from CA $1,021 on Expedia, you'll be pleasantly surprised at how much a vacation to Annapolis costs! Our packages simplify travel planning and maximize your savings.

What are the cheapest months to go to Annapolis?

Plan your getaway for the off-peak season and you're likely to find cheap Annapolis vacation packages. Remember that public holidays and local events and festivals can have an impact on prices, so do your research before booking.

How many days is enough for Annapolis?

With a well-organized schedule, you can easily visit the top Annapolis sights in a handful of days. But if you prefer to explore off the beaten track or take day trips, consider booking your Annapolis vacation for longer.

How to find the best Annapolis package deals?

Use Expedia's filter tool to find some terrific 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 browse for Annapolis package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.

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

You can enjoy significant savings on your Annapolis retreat by booking a customized vacation package. Click on the "Package" heading, then select your travel dates and destination to view some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.

When to book a vacation package to Annapolis?

Score incredible bargains by reserving your flights early with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for a spur-of-the-moment Annapolis break.

How to plan a trip to Annapolis?

  1. Pick your dates: The things you plan to do in Annapolis and your preferred season will help you decide when to go.
  2. Calculate your budget: Ensure you have enough money to cover everything from transportation and meals to activities and airfares. Your hotel will likely be the largest expense during your trip to Annapolis.
  3. Work out your trip length: Think about how long you'd like to spend discovering Annapolis. Plan your days so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Combine your accommodations and airfare: Once you've nailed down your trip dates and duration, book the perfect Annapolis vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.