Annapolis Vacations from $270
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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.
The Wildwood Hotel
$270
per person
Dec 21 - Dec 24
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to St. Louis (STL)
9.2/10 Wonderful! (1,672 reviews)
Would of been great if the fire alarm didn’t malfunction at 4:30am and the ran out of breakfast items
Reviewed on Sep 25, 2026
The Cheshire
$524
per person
Oct 27 - Oct 30
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to St. Louis (STL)
8.8/10 Excellent! (1,004 reviews)
Just stayed one night with my husband but we want to come back. Good location, loved the British theme going, breakfast was excellent, fun exploring all the floors in the hotel as it has 4 floors. Did not visit the restaurants but I bet they were good and they gave us a coupon to user but we did not as we checked in late. Our room was quiet on the first floor. Good parking available. Staff were friendly and helpful during our whole stay. Loved the room author thing going on and labels on doors as it was fun to read, lots of good artwork, loved the author of your room having a book in the room like ours was Ann Sewell who wrote Black Beauty and we had a paper back copy of it in our room. If I was to ask for anything , it would be a small refrigerator as my husband travels with meds and a grab bar to step out of the tub.
Would highly recommend.
Reviewed on Sep 25, 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
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
Relaxing 3B Log Home-15 min walk to the Black River!
Annapolis MO
8.8/10 Excellent! (12 reviews)
"This luxury cabin was the perfect getaway. For a remote location it has everything to keep a family busy happy and comfortable. The little details so well thought of from all the kitchen amenities to full closet of family games for the little and the older. Plenty of towels and blankets all clean ..."
Reviewed on Jun 23, 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 $270 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.
