Annapolis Vacations from $406

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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.

The Latest Annapolis vacation packages

Price found within the past 48 hours. Click for updated prices.
Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

4 out of 5
Grand Center
Price was $500, price is now $406 per person
$406
per person
Dec 30 - Jan 1
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to St. Louis (STL)
8.8/10 Excellent! (1,013 reviews)
Very enjoyable and unique.

Reviewed on Oct 25, 2025

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
Price was $851, price is now $480 per person
$480
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
9.2/10 Wonderful! (1,591 reviews)
Pool was good and clean but cold. Lol.

Reviewed on Oct 24, 2025

Hilton Garden Inn Chesterfield

Hilton Garden Inn Chesterfield

3 out of 5
Price was $768, price is now $595 per person
$595
per person
Jan 5 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to St. Louis (STL)
8.2/10 Very Good! (767 reviews)
Staff was courteous.

Reviewed on Oct 26, 2025

Spacious 3-Bedroom with King Bed

Spacious 3-Bedroom with King Bed

4 out of 5
Central West End
Price was $1,035, price is now $827 per person
$827
per person
Dec 23 - Dec 26
found 14 hours ago
Roundtrip flight included
Houston (HOU) to St. Louis (STL)
8.6/10 Excellent! (10 reviews)
Overall, we loved the apartment. It was cute, beds were very comfortable.

Reviewed on May 8, 2025

Marriott St. Louis West

Marriott St. Louis West

3.5 out of 5
Price was $960, price is now $769 per person
$769
per person
Jan 5 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to St. Louis (STL)
8.6/10 Excellent! (1,001 reviews)
Parking area felt very safe

Reviewed on Oct 14, 2025

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Discover the most popular places to visit in Annapolis

K Bridge Recreation Area

5/5(1 review)

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

Walnut Hollow Lake

Commune with nature and explore the great outdoors at Walnut Hollow Lake during your travels in Annapolis. Wander the parks and riverfront while you're in the area.

Walnut Hollow Lake

Annapolis Hotel Deals

Rustic River Cabin Getaway

Rustic River Cabin Getaway

Annapolis
9.6/10 Exceptional! (79 reviews)
I love this propery and it's location. I only took a star off because the showerhead has needed to be replaced since my 1st stay here a year ago and the ground floor beds need new mattresses or else some padding added. This would in no way keep me from staying here again, as the location and river ...

Reviewed on Sep 8, 2025

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Rustic River Cabin Getaway
Hillside Cabin #2 Annapolis, MO Black River

Hillside Cabin #2 Annapolis, MO Black River

Annapolis
$217 nightly
The price is $217 total per night from Oct 27 to Oct 28
$217 total
Oct 27 - Oct 28
Total with taxes and fees
9.4/10 Exceptional! (58 reviews)
great place to get away. plan to cook/grill there, or drive 30 minutes for food. however, this solitude and quiet is exactly why we booked here. and gorgeous roads, hikes, sites in every direction.

Reviewed on Aug 25, 2025

Hillside Cabin #2 Annapolis, MO Black River
New Cabin Just Minutes from Black River

New Cabin Just Minutes from Black River

Annapolis
$252 nightly
The price is $252 total per night from Oct 30 to Oct 31
$252 total
Oct 30 - Oct 31
Total with taxes and fees
8.4/10 Very Good! (5 reviews)
40th Birhday getaway
I rented this place for my 40th birthday. We went on a float trip near by, so we weren't in the house the majority of the day. But it was great place to come back to and play some games and hang out. There were 9 of us who stayed and we never felt crowded.

Reviewed on Jul 28, 2025

New Cabin Just Minutes from Black River
See all 120 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.

Find the Best Annapolis Vacation Packages

Annapolis Essential Information

Language
English
Currency
U.S dollars
Population
350
Max Temp Winter
40ºF
Max Temp Summer
85ºF
Top Sights
K Bridge Recreation Area, Walnut Hollow Lake and Crane Lake Recreation Area

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Frequently asked questions

How much does an Annapolis vacation package cost?
You can grab a vacation package to this top destination from $406 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.