Annapolis Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to NT$5,067 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    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! (290 reviews)
"The beds were super comfy, it was really clean, only problem I had was being able to work the TV, and that's only because I haven't had cable in so long... My fault not theirs.. lol"

Reviewed on 2025/8/16

Get rates
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 NT$2,565 per night from Aug 28 to Aug 29
NT$2,565
NT$2,802 total
Aug 28 - Aug 29
includes taxes & fees
7.4/10 Good! (286 reviews)
"."

Reviewed on 2025/8/13

Madison Inn Lodge
Fort Davidson Hotel

Fort Davidson Hotel

2.5 out of 5
310 South McCune St, Pilot Knob, Ironton, MO
Fully refundableReserve now, pay when you stay
The price is NT$3,959 per night from Aug 19 to Aug 20
NT$3,959
NT$4,325 total
Aug 19 - Aug 20
includes taxes & fees
9/10 Wonderful! (168 reviews)
Thought it would be newer
"I was a little disappointed when I pulled up to the hotel. I paid $163 for 1 week night(Wed). I expected it to be nicer & newer. The room was clean, the check in process was simple & the lady that checked me in was super friendly & was full of info. Overall it was a great stay."

Reviewed on 2025/8/13

Fort Davidson Hotel
See all 122 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.

Discover the most popular places to visit in Annapolis

K Bridge Recreation Area

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

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.