Annapolis Vacations from $292

Book a Hotel + Flight or Car together to unlock savings

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.
Ameristar Casino Resort and Spa

Ameristar Casino Resort and Spa

4.5 out of 5
Save 100% on your flight
Price was $381, price is now $292 per person
$292
per person
Jun 6 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.4/10 Very Good! (1,003 reviews)
They need a better Breakfast / Lunch area. Copper Wisk is to small and you have to stand in line to get waited on.

Reviewed on Apr 28, 2026

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
Price was $584, price is now $317 per person
$317
per person
Jun 17 - Jun 20
found 1 day ago
Roundtrip flight included
Denver (DEN) to St. Louis (STL)
9.2/10 Wonderful! (1,625 reviews)
Another great stay at the Wildwood, clean rooms, comfy bed, really all you need for a quick trip out to visit friends!!

Reviewed on Apr 28, 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
Save 100% on your flight
Price was $681, price is now $491 per person
$491
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (1,059 reviews)
Rooftop bar was awesome!

Reviewed on Apr 29, 2026

DoubleTree by Hilton Hotel St. Louis - Chesterfield

DoubleTree by Hilton Hotel St. Louis - Chesterfield

4 out of 5
Save 100% on your flight
Price was $488, price is now $357 per person
$357
per person
Jun 6 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.6/10 Excellent! (1,002 reviews)
Room smelled musty. Hairs in shower.

Reviewed on Apr 27, 2026

Up Up and Away Lodging

Up Up and Away Lodging

4 out of 5
Save 100% on your flight
Price was $1,170, price is now $897 per person
$897
per person
Jun 8 - Jun 13
just found
Roundtrip flight included
New York (NYC) to St. Louis (STL)
9.4/10 Exceptional! (27 reviews)
Yes! The room was beautiful. Very clean. Beth was an amazing hostess, and the breakfast hit the spot. I highly recommend the stay, and when I return, I will do the same B&B. Thanks, Beth!

Reviewed on Dec 5, 2025

Don't see what you're looking for?
See all available trips from Columbus to Annapolis
View all trips

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 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

Get rates
Rustic River Cabin Getaway
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.
FS Rental #4 Annapolis, MO Black River

FS Rental #4 Annapolis, MO Black River

Annapolis MO
$211 nightly
The price is $211 total per night from Apr 30 to May 1
$211 total
Apr 30 - May 1
Total with taxes and fees
9.6/10 Exceptional! (7 reviews)
This was a great place to stay, so close to my job site. Comfortable, clean and well furnished. I would definitely stay here again!

Reviewed on Oct 30, 2025

FS Rental #4 Annapolis, MO Black River
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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does an Annapolis vacation package cost?
You can grab a vacation package to this top destination from $292 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.