Annapolis Vacations from $455

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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.
White House at Grand Central

White House at Grand Central

4 out of 5
Grand Center
Price was $674, price is now $455 per person
$455
per person
Mar 15 - Mar 20
found 17 hours ago
Roundtrip flight included
New York (NYC) to St. Louis (STL)
8.6/10 Excellent! (123 reviews)
Very clean and very friendly people

Reviewed on Nov 11, 2025

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was $749, price is now $462 per person
$462
per person
Mar 30 - Apr 2
found 2 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to St. Louis (STL)
9.2/10 Wonderful! (1,600 reviews)
We enjoyed our stay! Close to skiing and tubing. Lots of restaurants close. Kids loves the small swimming pool

Reviewed on Jan 7, 2026

Hermann Grain Bins BNB

Hermann Grain Bins BNB

2 out of 5
Save 100% on your flight
Price was $1,369, price is now $959 per person
$959
per person
Feb 12 - Feb 16
found 2 hours ago
Roundtrip flight included
New York (NYC) to St. Louis (STL)
2/10 (1 review)
21C Museum Hotel St Louis

21C Museum Hotel St Louis

4.5 out of 5
Downtown West
Price was $790, price is now $581 per person
$581
per person
Mar 15 - Mar 20
found 17 hours ago
Roundtrip flight included
New York (NYC) to St. Louis (STL)
9/10 Wonderful! (1,458 reviews)
Our room wasn’t ready at 5pm, could not check in for about 1.5 hrs. Luckily they have a fantastic bar. Room was small but well appointed. The doors to some cabinets would not shut. The shower door would not shut. We did not have enough shampoo conditioner or body wash. The museum was nice. The restaurant is great. Probably wouldn’t stay again but would definitely eat at the restaurant or have drinks at the bar.

Reviewed on Jan 5, 2026

Hilton Pennywell St. Louis at the Arch

Hilton Pennywell St. Louis at the Arch

4 out of 5
Downtown St. Louis
Price was $874, price is now $671 per person
$671
per person
Mar 15 - Mar 20
found 17 hours ago
Roundtrip flight included
New York (NYC) to St. Louis (STL)
8.8/10 Excellent! (996 reviews)
Beautiful hotel, very clean. Dinner at restaurant was subpar.

Reviewed on Jan 7, 2026

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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
9.6/10 Exceptional! (80 reviews)
Wonderful location! This is the third October me and my friends come down to relax, unwind, and reconnect. We look forward to 2026 being pir 4th trip to the cabin!

Reviewed on Oct 26, 2025

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

Hillside Cabin #1 Annapolis, MO Black River

Annapolis MO
$255 nightly
The price is $255 total per night from Jan 9 to Jan 10
$255 total
Jan 9 - Jan 10
Total with taxes and fees
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! (55 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 133 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 $455 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.