Annapolis Vacations from $309
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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.
StayAtlas Retreat w/ Pool, Gym, Games, BBQ
Mount Pleasant
$3,011
per person
Dec 23 - Dec 30
found 12 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to St. Louis (STL)
10/10 Exceptional! (1 review)
The property was such a fun surprise- the neighborhood was a little sketchy, but it was great on the inside and the backyard... Great experience, fun complimentary toiletries, etc
Reviewed on Sep 25, 2026
Hermann Grain Bins BNB
$1,938
per person
Dec 23 - Dec 30
found 13 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to St. Louis (STL)
6/10 (2 reviews)
It was so comfortable and uniquely and beautifully decorated! There was so many awesome areas to explore inside and outside of the Grain Bins. Food provided for breakfast was fresh and hot. There was perfectly cooked bacon, scrambled eggs and really moist corn muffins with homemade mango preservers! We were welcomed with fresh, homemade plum bread. Instructions for everything available to utilize and operate were easy to understand. I can’t wait to go back and I will tell all my friends and family about this unique and relaxing place.
Reviewed on May 22, 2026
Stay near popular Annapolis attractions
K Bridge Recreation Area
9.6/10 (4 reviews)
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.
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.
Annapolis Hotel Deals
Panther Den Cabin is located 4 miles from Hwy K Campground
Annapolis. MO
9.4/10 Exceptional! (16 reviews)
"Had everything we needed just in town and we prefer a more country setting!!! Very clean!!"
Reviewed on Aug 17, 2026
Hillside Cabin #2 Annapolis, MO Black River
Annapolis MO
$217 nightly
$217 total
Oct 18 - Oct 19
Total with taxes and fees
9.4/10 Exceptional! (65 reviews)
"Very nice"
Reviewed on Sep 26, 2026
Hunters/Floaters Welcome! Creekside Missouri Cabin
Annapolis MO
10/10 Exceptional! (2 reviews)
"Great weekend in a very peaceful atmosphere! Very clean! Creek was fun for 7 year-old grandson. Had fire pit and space to play games! Perfect for our needs!"
Reviewed on Jul 20, 2026
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 $309 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.
