Annapolis Holidays

    Plan, book, travel with confidence
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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

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$111 per night from 1 Dec to 2 Dec
S$111
includes taxes & fees
1 Dec - 2 Dec
7.4/10 Good! (252 reviews)
"Madison Inn is a cute and cozy place. The 2 issues I had was the room I stayed could use a little deep cleaning and the other is when you send house keeping around please have them knock. On our second morning some man who said he was house keeping tried to open our door. If the metal security lock ..."

Reviewed on 13 Oct,2024

Madison Inn Lodge
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$156 per night from 7 Nov to 8 Nov
S$156
includes taxes & fees
7 Nov - 8 Nov
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
Black River Motel and Restaurant
Black River Motel and Restaurant
2 out of 5
32970 Missouri Higway 21, Lesterville, MO
The price is S$180 per night from 6 Nov to 7 Nov
S$180
includes taxes & fees
6 Nov - 7 Nov
7.6/10 Good! (16 reviews)
"We very much enjoyed our stay. After dinner we sat outside by the fire pit and my husband enjoyed Icecream on the house!!"

Reviewed on 5 Oct,2024

Black River Motel and Restaurant
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.