Annapolis Vacations from $305
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The Latest Annapolis Vacation Packages
- The Cheshire
Sep 4 - Sep 7The Cheshire + Flight
Richmond Heights3 nights4.0 star property8.8/10 - Excellent (1,004 reviews)"The boutique hotel was a very neat experience. The staff was very helpful. It was a central location for the things we wanted to do while in St. Louis."Reviewed July 26, 2026Roundtrip • Atlanta (ATL) - St. Louis (STL)ATL - STL • Nonstop STL - ATL • Nonstop - The Wildwood Hotel
Sep 27 - Oct 2The Wildwood Hotel + Flight
Wildwood5 nights3.5 star property9.2/10 - Wonderful (1,672 reviews)"The hotel was really clean! Beds were cozy and the hotel breakfast was good!"Reviewed July 27, 2026Roundtrip • Atlanta (ATL) - St. Louis (STL)ATL - STL • Nonstop STL - ATL • Nonstop - Remodeled and Inviting Free EV
Sep 12 - Sep 17Remodeled and Inviting Free EV + Flight
Fenton5 nights2.0 star property10/10 - Exceptional (1 review)"The property was excellent, and the home was very warm and welcoming."Reviewed June 25, 2026Roundtrip • Atlanta (ATL) - St. Louis (STL)ATL - STL • Nonstop STL - ATL • Nonstop - Residence Inn by Marriott St. Louis West County
Sep 27 - Oct 2Residence Inn by Marriott St. Louis West County + Flight
Town and Country5 nights3.0 star property9.2/10 - Wonderful (262 reviews)Roundtrip • Atlanta (ATL) - St. Louis (STL)ATL - STL • Nonstop STL - ATL • Nonstop - Crowne Plaza St. Louis Airport by IHG
Sep 12 - Sep 17Crowne Plaza St. Louis Airport by IHG + Flight
Bridgeton5 nights3.5 star property8.0/10 - Very Good (1,002 reviews)"It's a very nice hotel. My only problem was that the refrigerator in my room was malfunctioning & I have medication that required refrigeration. So I had to keep it in ice bucket for the night. They offered to keep it in hotel refrigerator but that was not acceptable for me. But they were looking for a replacement & never returned the call as to what happened."Reviewed July 27, 2026Roundtrip • Atlanta (ATL) - St. Louis (STL)ATL - STL • Nonstop STL - ATL • Nonstop
Annapolis Hotel Deals
Black River Motel and Restaurant
Black River Motel and Restaurant
Ironton Hub: Near Elephant Rocks & Shut-ins
Ironton Hub: Near Elephant Rocks & Shut-insFrequently Asked Questions
How much does an Annapolis vacation package cost?
You can grab a vacation package to this top destination from $305 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.