Annapolis Holidays

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    Better together
    Save up to S$134 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

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! (276 reviews)
"Great"

Reviewed on 12 Jun, 2025

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 S$122 per night from 7 Jul to 8 Jul
S$122
7 Jul - 8 Jul
includes taxes & fees
7.4/10 Good! (277 reviews)
"Easy to find. Quiet and comfortable."

Reviewed on 7 Jun, 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 S$175 per night from 16 Jun to 17 Jun
S$175
16 Jun - 17 Jun
includes taxes & fees
8.2/10 Very Good! (23 reviews)
"The room was comfortable. The towels were very soft."

Reviewed on 12 Jun, 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 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.