Annapolis Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Annapolis

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! (288 reviews)
Great place to stay!
"We had a great stay at the Shepherd Mountain Inn. The staff was wonderful, the rooms were clean and comfortable. The breakfast was delicious. We highly recommend it!"

Reviewed on 27 Jul 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 2.242.158 ₫ per night from 28 Aug to 29 Aug
2.242.158 ₫
2.449.042 ₫ total
28 Aug - 29 Aug
includes taxes & fees
7.4/10 Good! (284 reviews)
"Close to Hwy 67 in Fredericktown, Mo. Internet access was good. Quiet overall. I needed to get up very early to be somewhere at 6 am and able to get up, shower and out the door without any delays."

Reviewed on 3 Aug 2025

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 3.461.172 ₫ per night from 12 Aug to 13 Aug
3.461.172 ₫
3.780.544 ₫ total
12 Aug - 13 Aug
includes taxes & fees
9/10 Wonderful! (167 reviews)
"Pool very clean and outdoors! The historic battle fields, exploration and early exploration of Americ hiking is a must do when visiting."

Reviewed on 8 Aug 2025

Fort Davidson Hotel
See all 113 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 holiday package cost?
You can grab a holiday package to this top destination on Expedia. However, how much your holiday 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 holiday packages, organise 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 holiday 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 holiday package as early as possible.
Is it cheaper to book an Annapolis holiday as a package?
Expedia holiday 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 customised Annapolis holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday package to Annapolis?
If you've got your Annapolis holiday 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 travelling 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 favourite 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 holiday. Put together a draft plan and allocate enough time for all the things you want to do.
  4. Bundle your accommodation and airfare: After you've nailed down your dates and duration, lock in the ideal Annapolis holiday package for you.