Annapolis Vacations from ￥154,448

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The Latest Annapolis Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
per person
Sep 16 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to St. Louis (STL)
9.2/10 Wonderful! (1,550 reviews)
Great place! Super safe and quiet

Reviewed on Aug 4, 2025

Hilton Pennywell St. Louis at the Arch

Hilton Pennywell St. Louis at the Arch

4 out of 5
Downtown St. Louis
per person
Sep 16 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to St. Louis (STL)
8.8/10 Excellent! (869 reviews)
Good area for tourism

Reviewed on Aug 5, 2025

Courtyard by Marriott St. Louis Downtown/Convention Center

Courtyard by Marriott St. Louis Downtown/Convention Center

3 out of 5
Downtown St. Louis
per person
Sep 16 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to St. Louis (STL)
9/10 Wonderful! (1,006 reviews)
Staff was amazing, friendly and very helpfull. Would stay again in a heartbeat.

Reviewed on Aug 4, 2025

Embassy Suites by Hilton St. Louis Downtown

Embassy Suites by Hilton St. Louis Downtown

4 out of 5
Downtown St. Louis
per person
Sep 16 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to St. Louis (STL)
8.8/10 Excellent! (1,201 reviews)
The room was supposed my expectations

Reviewed on Aug 4, 2025

Ameristar Casino Resort and Spa

Ameristar Casino Resort and Spa

4.5 out of 5
per person
Sep 16 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to St. Louis (STL)
8.4/10 Very Good! (1,003 reviews)
We love staying at the hotel for its great service, clean rooms and awesome restaurant food. BUT, THE CASINO HAS BEEN PAYING LESS AND LESS. WE WOULD NOT RECOMMEND THE CASINO...THE PAYOUTS ARE TERRIBLE ESPECIALLY FOR A HOLIDAY WEEKEND LIKE THE 4TH OF JULY

Reviewed on Aug 4, 2025

Find the Best Annapolis Vacation Packages

Annapolis Hotel Deals

Rustic River Cabin Getaway

Rustic River Cabin Getaway

Annapolis
9.6/10 Exceptional! (73 reviews)
Wonderful stay.
"This was our second stay here and we are trying to make it an annual trip. Cabin is awesome along with location on the river, you can’t beat it."

Reviewed on Jul 16, 2025

Get rates
Rustic River Cabin Getaway
Make your reservation fast as inquiries are coming in daily.

Make your reservation fast as inquiries are coming in daily.

Redford
9.8/10 Exceptional! (52 reviews)
"We loved the view from overlook cabin. Cabin was clean and cozy. Follow directions property manager sends you because gps will try to take you on a scavenger hunt but this was my fault. Accessing river a sxs or 4x4 definitely needed due to river being up. Very peaceful setting at river and ..."

Reviewed on Jun 5, 2025

Get rates
Make your reservation fast as inquiries are coming in daily.
Hillside Cabin #4 Annapolis, MO Black River

Hillside Cabin #4 Annapolis, MO Black River

Annapolis
The price is ￥27,859 per night from Aug 6 to Aug 7
￥27,859
￥47,021 total
Aug 6 - Aug 7
includes taxes & fees
9.6/10 Exceptional! (36 reviews)
"It was nice. The only thing it needs is a coffee table."

Reviewed on Jun 13, 2025

Hillside Cabin #4 Annapolis, MO Black River
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 vacation package cost?
You can grab a vacation package to this top destination from ￥154,448 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.