Annapolis Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.
Moonrise Hotel

Moonrise Hotel

4 out of 5
Delmar Loop
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to St. Louis (STL)
9/10 Wonderful! (1,783 reviews)
Fun hotel to stay at. A littways from downtown but has a couple cool late night spots right next door. Great place to stay if going to a show at The Pageabut also has mini golf across the street, and late night bowling next door. Hotel is unique and rooftop was a great place to relax. Would definitely stay again.

Reviewed on Jul. 16, 2025

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
per person
Sep 4 - Sep 7
found 20 hours ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
9/10 Wonderful! (1,549 reviews)
The room was ok, tired decor (a mix between The Sopranos and Hobby Lobby), slightly dirty furniture (sofa and arm chair). Bathroom was clean, fan didn’t pull all the moisture out. We traveled for a medical appointment in Saint Louis and I barely got any rest on the cheap springy mattress (we are 40, and in healthy shape). Breakfast was horrible: three waffle makers(why?!), some cereal, microwaveable Jimmy Dean sandwiches instead of ANY hot dishes, Great Valley granola bars, a thermos of coffee, decaf, and coffee-flavored hot water for Lipton tea. Lovely staff, but not enough for us to come back again.

Reviewed on Jul. 13, 2025

Ballpark Apartments by Barsala

Ballpark Apartments by Barsala

4 out of 5
Downtown St. Louis
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to St. Louis (STL)
7.4/10 Good! (9 reviews)
It's a great location, right across from the Ballpark. It is a fairly spartan apartment set-up, with concrete floors.. a little surprising? Parking is on the street or in a pay lot.

Reviewed on Jun. 8, 2025

Hilton Garden Inn Chesterfield

Hilton Garden Inn Chesterfield

3 out of 5
per person
Sep 15 - Sep 19
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Louis (STL)
8.2/10 Very Good! (756 reviews)
The stay was too short

Reviewed on Jul. 2, 2025

The Cheshire

The Cheshire

4 out of 5
per person
Sep 15 - Sep 19
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Louis (STL)
8.6/10 Excellent! (1,000 reviews)
Would definitely go back

Reviewed on Jul. 12, 2025

Ready to book your vacation to Annapolis?

 

Choose your dates

Annapolis Hotel Deals

Make your reservation fast as inquiries are coming in daily.

Make your reservation fast as inquiries are coming in daily.

Redford
9.8/10 Exceptional! (52 reviews)
"We loved the view from overlook cabin. Cabin was clean and cozy. Follow directions property manager sends you because gps will try to take you on a scavenger hunt but this was my fault. Accessing river a sxs or 4x4 definitely needed due to river being up. Very peaceful setting at river and ..."

Reviewed on Jun. 5, 2025

Get rates
Make your reservation fast as inquiries are coming in daily.
Rustic River Cabin Getaway

Rustic River Cabin Getaway

Annapolis
9.6/10 Exceptional! (72 reviews)
Unplugged family trip
"This is the best place to get your family together and family members off devices. I hope the owners never get Wi-Fi or cell service to the cabin. God’s country is beautiful!"

Reviewed on Jul. 4, 2025

Get rates
Rustic River Cabin Getaway
Hillside Cabin #4 Annapolis, MO Black River

Hillside Cabin #4 Annapolis, MO Black River

Annapolis
The price is CA $259 per night from Aug 4 to Aug 5
CA $259
CA $437 total
Aug 4 - Aug 5
includes taxes & fees
9.6/10 Exceptional! (36 reviews)
"It was nice. The only thing it needs is a coffee table."

Reviewed on Jun. 13, 2025

Hillside Cabin #4 Annapolis, MO Black River
See all 111 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 Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Discover the most popular places to visit in Annapolis

K Bridge Recreation Area

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.

K Bridge Recreation Area

Frequently asked questions

How much does an Annapolis vacation package cost?
Offering excellent value package deals from CA $768 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.