Annapolis Vacations from $249
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The Latest Annapolis Vacation Packages
- The Wildwood Hotel
Oct 22 - Oct 25The Wildwood Hotel + Flight
Wildwood3 nights3.5 star property9.2/10 - Wonderful (1,663 reviews)"Very nice stay, enjoyed everything about it, especially the extraordinarily courteous staff"Reviewed July 28, 2026Roundtrip • Atlanta (ATL) - St. Louis (STL)ATL - STL • Nonstop STL - ATL • Nonstop$512$249found 2 days agoper traveler - Remodeled and Inviting Free EV
Sep 17 - Sep 22Remodeled 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 - The Cheshire
Oct 22 - Oct 25The Cheshire + Flight
Richmond Heights3 nights4.0 star property8.8/10 - Excellent (1,006 reviews)Roundtrip • Atlanta (ATL) - St. Louis (STL)ATL - STL • Nonstop STL - ATL • Nonstop - The Principal Hotel
Oct 20 - Oct 24The Principal Hotel + Flight
Columbia4 nights3.5 star property9.6/10 - Exceptional (347 reviews)Roundtrip • Denver (DEN) - St. Louis (STL)DEN - STL • Nonstop STL - DEN • Nonstop - Hermann Grain Bins BNB
Oct 22 - Oct 25Hermann Grain Bins BNB + Flight
Hermann3 nights2.0 star property6.0/10 - (2 reviews)"It was so comfortable and uniquely and beautifully decorated! There was so many awesome areas to explore inside and outside of the Grain Bins. Food provided for breakfast was fresh and hot. There was perfectly cooked bacon, scrambled eggs and really moist corn muffins with homemade mango preservers! We were welcomed with fresh, homemade plum bread. Instructions for everything available to utilize and operate were easy to understand. I can’t wait to go back and I will tell all my friends and..."Reviewed May 22, 2026Roundtrip • Dallas (DFW) - St. Louis (STL)DFW - STL • Nonstop STL - DFW • 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 $249 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.