Annapolis Vacations from $277

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Your Annapolis Vacation

Pick a Annapolis vacation package and focus on what counts — having some fun. No more planning headaches, just a lot more free time to uncover what's special about this lively city, such as its rich history and coastal scenery. Fill your days with tours of K Bridge Recreation Area, Crane Lake Recreation Area and Walnut Hollow Lake, some of the attractions you should see during your trip to Annapolis. A couple of quick clicks is all it takes to build a customized Annapolis vacation on Expedia.

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
Save 100% on your flight
per person
Sep 21 - Sep 23
found 14 hours ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
9.2/10 Wonderful! (1,558 reviews)
Very lovely place to stay the night is you are in the St Louis area.

Reviewed on Aug 12, 2025

The Principal Hotel

The Principal Hotel

3.5 out of 5
Save 100% on your flight
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
9.8/10 Exceptional! (111 reviews)
Love staying here! The staff is very nice & always making sure you have what you need!

Reviewed on Aug 10, 2025

Hilton Garden Inn Chesterfield

Hilton Garden Inn Chesterfield

3 out of 5
per person
Sep 24 - Sep 27
found 12 hours ago
Roundtrip flight included
Dallas (DAL) to St. Louis (STL)
8.2/10 Very Good! (760 reviews)
I booked online and paid via the app. When I arrived on site they explained they had overbooked and had no rooms available. The staff was amazing and went above and beyond and secured a room at another location. Thank you to the staff for taking care of us.

Reviewed on Jul 26, 2025

Holiday Inn Express & Suites St. Louis West - Fenton by IHG

Holiday Inn Express & Suites St. Louis West - Fenton by IHG

3 out of 5
per person
Sep 24 - Sep 27
found 12 hours ago
Roundtrip flight included
Dallas (DAL) to St. Louis (STL)
8.8/10 Excellent! (1,001 reviews)
great hotel clean and staff was fantasic

Reviewed on Aug 3, 2025

The Cheshire

The Cheshire

4 out of 5
per person
Sep 24 - Sep 27
found 12 hours ago
Roundtrip flight included
Dallas (DAL) to St. Louis (STL)
8.6/10 Excellent! (1,000 reviews)
Bed and pillows where uncomfortable. Room and facilities were dirty. Parking was a joke due to there being 2 restaurants on the property as well so it was hard to find a spot as the hotel and restaurant shared the parking lot and garage but you had to pay to park if you stayed in the hotel.

Reviewed on Aug 3, 2025

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Discover the most popular places to visit in Annapolis

K Bridge Recreation Area

Explore the great outdoors at K Bridge Recreation Area, a lovely green space in Annapolis. While you're in the area, stroll along the riverfront.

K Bridge Recreation Area

Walnut Hollow Lake

Commune with nature and explore the great outdoors at Walnut Hollow Lake during your travels in Annapolis. Wander the parks and riverfront while you're in the area.

Walnut Hollow Lake

Annapolis Hotel Deals

Rustic River Cabin Getaway

Rustic River Cabin Getaway

Annapolis
9.6/10 Exceptional! (75 reviews)
"Right by the black river. Cabin was amazing. It's very secluded. Our host was great! Nice and clean!"

Reviewed on Aug 6, 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! (53 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
$273 nightly
The price is $273 total per night from Sep 3 to Sep 4
$273 total
Sep 3 - Sep 4
Total includes taxes and 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.

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Frequently asked questions

How much does an Annapolis vacation package cost?
You can grab a vacation package to this top destination from $277 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?
You can typically find lower prices and greater availability in January, February and November. Explore our cheap Annapolis vacation packages and you could get some great off-season discounts.
How many days is enough for Annapolis?
The ideal length of your Annapolis vacation depends on what you'd like to see. Usually, a few days to a week will give you plenty of time to tick off all the top sights and discover some hidden treasures 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.
Does Expedia offer Book Now, Pay Later Annapolis vacation packages?
Your Annapolis trip should be a relaxing escape from your busy life, not a source of money worries. So to give you that extra flexibility, we've joined up with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.