Annapolis Holidays

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    Save up to S$134 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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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
The price is S$159 per night from 8 Dec to 9 Dec
S$159
includes taxes & fees
8 Dec - 9 Dec
9.2/10 Wonderful! (260 reviews)
"This is a nice quiet little motel. Nothing fancy, but clean, close to a good restaurant, and very friendly staff."

Reviewed on 29 Oct,2024

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$118 per night from 5 Dec to 6 Dec
S$118
includes taxes & fees
5 Dec - 6 Dec
7.4/10 Good! (255 reviews)
"Good"

Reviewed on 10 Nov,2024

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 S$194 per night from 7 Dec to 8 Dec
S$194
includes taxes & fees
7 Dec - 8 Dec
9/10 Wonderful! (156 reviews)
Old but nice hotel
"The hotel itself and the room was very dated. But it was clean, quiet, and the bed was comfortable. No breakfast. For a one night stay while on a long trip it was good."

Reviewed on 12 Oct,2024

Fort Davidson Hotel
See all 115 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?
From as low as . Yes, you read that right. Our Annapolis packages are a simple way to stretch your budget further. Bundle your favourite hotels, flights and rental car and get out and see this vibrant destination.
How do I get a cheap travel package to Annapolis?
It’s easy. Just bundle. Hotels, flights and rental cars — combine whatever you need into an Annapolis holiday package and save. Score even better deals when you add extras such as activities or tours to your booking. But that’s not the only good part. You have the freedom to customize your trip your way. We offer over 550 air carriers and 1,000,000 hotels across the world, so that everyone has a chance to travel and live out those holiday fantasies.
Where should I stay in Annapolis?
Annapolis boasts numerous terrific places to explore, like K Bridge Recreation Area. Stay somewhere nearby and make sightseeing easier.
What are the top hotels in Annapolis?
If it’s your first visit to Annapolis, book a room at Panther Den Cabin Is Located 4 Miles From Hwy K Campground or Rustic River Cabin Getaway. Both will make you feel at home and are favourites with lots of travellers.
How far in advance should I book my Annapolis holiday?
Your safest bet is to book early. Air carriers typically advertise flights nearly 12 months prior to departure, and this is a great opportunity to score some rock-bottom prices. Boss just told you to use up all your holiday days next month? Don’t fret. Expedia are never short on fantastic bargains to help you have the getaway of your dreams, at a price you can afford.
What does an Expedia Annapolis travel package include?
With Expedia, you can choose any combination of flights, car rentals and hotels to create your ideal Annapolis package. Once you’ve made your booking, you can add on all the fun stuff like day tours and activities. Don’t forget — the more you bundle, the bigger the savings!
What should I know before booking an Annapolis travel package?
A package can be easier on the credit card than individually booking everything you need for your adventure. For example, bundle your hotels, flights and rental cars and save a tidy sum. Whatever your holiday plans, you’ll find a package to suit your budget.
Can I choose my airline with an Annapolis Expedia holiday package?
Yes, you’re in control. Expedia has access to more than 550 partner airlines all over the world, so you can tailor your Annapolis getaway according to your style and budget.
If I'm not able to travel, can I cancel my Annapolis holiday package?
If your travel plans in Annapolis have changed, it’s a relief to know that it’s possible to amend or cancel your booking. If your booking was made less than 24 hours ago, you may be able to get a refund. If your booking is older than that, your airline, hotel or car rental company may charge a fee. To learn more, visit our Customer Service Portal.

* 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.