Annapolis Vacations
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- Plan, book, travel with confidence
- Better togetherSave up to ₩1,660,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Find the Best Annapolis Vacation Packages
Annapolis Hotel Deals
Shepherd Mountain Inn
1321 N Hwy 21 Ironton MO
Fully refundableReserve now, pay when you stay
₩174,161
₩190,235 total
Sep 7 - Sep 8
includes taxes & fees
9.2/10 Wonderful! (325 reviews)
"We love the motel vibe and that's exactly what we got! The owner of the property and the restaurant was at the front desk when we arrived, and he was super friendly and helpful. He even gave us some samples of their beef sticks, which were phenomenal, and we highly recommend you ask about! The room ..."
Reviewed on Jul 28, 2026
Madison Inn Lodge
730 Plaza Drive Fredericktown MO
Fully refundableReserve now, pay when you stay
₩123,608
₩135,021 total
Aug 20 - Aug 21
includes taxes & fees
7.6/10 Good! (306 reviews)
"Room wasn’t all that clean. Had some questionable stains, kind of dusty, bath room needed a good deep clean. No bugs in the bed so I suppose that’s a huge plus! It was cheap for one night. Said it had breakfast in the AM, we weren’t that brave to try it."
Reviewed on Aug 9, 2026
Black River Motel and Restaurant
32970 Missouri Higway 21 Lesterville MO
₩164,630
₩174,056 total
Aug 13 - Aug 14
includes taxes & fees
8.6/10 Excellent! (46 reviews)
"Good hotel, but not much to do in town."
Reviewed on Aug 9, 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.
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.
Frequently asked questions
How much does an Annapolis vacation package cost?
You can grab a vacation package to this top destination 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?
To score cheap Annapolis vacation packages, organize your trip outside of peak times such as school holidays. You'll typically find better availability and lower prices in the off-season or when it's less busy.
How many days is enough for Annapolis?
The ideal duration for your Annapolis vacation depends on what you'd like to do. Typically, a few days to a week will give you plenty of time to go to all the major attractions and explore some hidden gems 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.
How to plan a trip to Annapolis?
- Pick your travel dates: The things you plan to do in Annapolis and your favorite season will help you decide when to get away.
- Work out your budget: Make sure you have enough money to cover everything from transportation and food to activities and flights. Your hotel will probably be the largest expense during your trip to Annapolis.
- Decide how long to go away for: Now that you're up to speed on Annapolis, you can work out the ideal length of your vacation. Put together a draft plan and allocate enough time for all the things you want to do.
- Bundle your accommodations and airfare: After you've nailed down your dates and duration, lock in the ideal Annapolis vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
