Annapolis Vacations

Book a Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to ₩234,741 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Find the Best Annapolis Vacation Packages

Annapolis Hotel Deals

Shepherd Mountain Inn
Shepherd Mountain Inn
2.5 out of 5
1321 N Hwy 21, Ironton, MO
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (277 reviews)
"We were very happy with our stay. Very clean, quiet and they brought us a flower in a vase! Lots of area attractions near by. Be sure to see the Battle Ground of Pilot Knob and Train Station that still has 2 stops a day!"

Reviewed on Jun 22, 2025

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Shepherd Mountain Inn
Madison Inn Lodge
Madison Inn Lodge
2.5 out of 5
730 Plaza Drive, Fredericktown, MO
Fully refundableReserve now, pay when you stay
The price is ₩119,101 per night from Jun 29 to Jun 30
₩119,101
₩130,098 total
Jun 29 - Jun 30
includes taxes & fees
7.4/10 Good! (277 reviews)
"Easy to find. Quiet and comfortable."

Reviewed on Jun 7, 2025

Madison Inn Lodge
Black River Motel and Restaurant
Black River Motel and Restaurant
2 out of 5
32970 Missouri Higway 21, Lesterville, MO
The price is ₩175,569 per night from Jun 29 to Jun 30
₩175,569
₩185,621 total
Jun 29 - Jun 30
includes taxes & fees
8.2/10 Very Good! (24 reviews)
"The room was comfortable. The towels were very soft."

Reviewed on Jun 12, 2025

Black River Motel and Restaurant
See all 112 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.

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?

  1. Pick your travel dates: The things you plan to do in Annapolis and your favorite season will help you decide when to get away.
  2. 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.
  3. 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.
  4. 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.