Annapolis Vacations from $321

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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.
HoteLumiere at the Arch - A Caesars Rewards Destination

HoteLumiere at the Arch - A Caesars Rewards Destination

4 out of 5
Downtown St. Louis
Price was $411, price is now $321 per person
$321
per person
Jul 20 - Jul 22
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
6.8/10 (1,000 reviews)
The casino was fun and clean. Could use more wait staff. The room was clean. So much so that there were no bath towels and body soap in the shower. We me tioned it at check out that i couldnt even shower before we left and she just handed me my receipt. I found that extremely rude. I guess at least she called housekeeping to cover the issue but it didnt take care of my issue in the least. Why pay the price we paid in order to not be able to use the facilities. I had no time to call for towels because i wouldnt have been able to get everything done before check out. We were up late gambling at the casino so late start in the morning. But we still should have had towels and soap since its worked i to the price of the room.

Reviewed on Apr 19, 2026

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was $643, price is now $430 per person
$430
per person
Jun 14 - Jun 17
found 1 hour ago
Roundtrip flight included
Dallas (DAL) to St. Louis (STL)
9.2/10 Wonderful! (1,624 reviews)
The hotel is really nice and close to good restaurants.

Reviewed on Apr 22, 2026

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 $560, price is now $426 per person
$426
per person
Jun 1 - Jun 4
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
8.8/10 Excellent! (1,056 reviews)
Hotel overall was great. The staff seemed confused and did not know how to handle the tornado sirens/severe weather situation with patrons. The instructed us to go to the second floor via the elevator? There were also no instructions posted on where to go in the event of severe weather.

Reviewed on Apr 21, 2026

Spacious 3-Bedroom with King Bed

Spacious 3-Bedroom with King Bed

4 out of 5
Central West End
Save 100% on your flight
Price was $1,255, price is now $960 per person
$960
per person
Jun 4 - Jun 8
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
8.8/10 Excellent! (11 reviews)
Clean room nice area

Reviewed on Feb 1, 2026

Hermann Grain Bins BNB

Hermann Grain Bins BNB

2 out of 5
Price was $1,622, price is now $1,264 per person
$1,264
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to St. Louis (STL)
2/10 (1 review)
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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

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 MO
9.8/10 Exceptional! (81 reviews)
This listing is perfect for pets and guests to be free and roam the beautiful river and country side. Its far away from noise and boasts the serenity and privacy we all need sometimes. Perfect for shutting off the phones and getting into nature. Thank you for sharing this place.

Reviewed on Apr 8, 2026

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Rustic River Cabin Getaway
Hillside Cabin #1 Annapolis, MO Black River

Hillside Cabin #1 Annapolis, MO Black River

Annapolis MO
$247 nightly
The price is $247 total per night from Apr 26 to Apr 27
$247 total
Apr 26 - Apr 27
Total with taxes and fees
9.4/10 Exceptional! (36 reviews)
Not clean
Pictures where deceiving- counter tops in kitchen only about 26” tall-entire facility was dirty with many cob webs

Reviewed on Sep 14, 2024

Hillside Cabin #1 Annapolis, MO Black River
Make your reservation fast as inquiries are coming in daily.

Make your reservation fast as inquiries are coming in daily.

Redford MO
9.8/10 Exceptional! (56 reviews)
Excellent property and location was awesome

Reviewed on Sep 9, 2025

Get rates
Make your reservation fast as inquiries are coming in daily.
See all 136 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 $321 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.