Annapolis Vacations
Pack those stellar shades. We have Annapolis vacation deals for you!
If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Annapolis – great memories and a tall tale or two.
Hotwire can help you find your travel bliss with Annapolis vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!
Pack everything you want – then take half of it out
We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.Bring comfortable walking shoes on your trip to Annapolis
No one should have to endure walking tours in dress shoes or high heels. No one.Bring photocopies of your passport or license
You flew home from a great Annapolis vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.Don’t underestimate the power of earplugs
Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.Always carry some cash
You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.Explore like a local
Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Annapolis well.Annapolis Flight + Hotel Packages
Mon, Dec 14 - Thu, Dec 17
O'Hare Intl. - Baltimore Washington Intl. Thurgood Marshall
$356
The price now is $243 per personFlight + Hotel
Tue, Dec 29 - Mon, Jan 4
O'Hare Intl. - Baltimore Washington Intl. Thurgood Marshall
$549
The price now is $383 per personFlight + Hotel
Tue, Dec 29 - Mon, Jan 4
O'Hare Intl. - Baltimore Washington Intl. Thurgood Marshall
$610
The price now is $434 per personFlight + Hotel
Mon, Dec 14 - Thu, Dec 17
O'Hare Intl. - Baltimore Washington Intl. Thurgood Marshall
$334
The price now is $241 per personFlight + Hotel
Fri, Dec 4 - Tue, Dec 8
O'Hare Intl. - Baltimore Washington Intl. Thurgood Marshall
$267
The price now is $200 per personFlight + Hotel
Mon, Dec 14 - Thu, Dec 17
O'Hare Intl. - Baltimore Washington Intl. Thurgood Marshall
$297
The price now is $226 per personFlight + Hotel
Tue, Dec 29 - Mon, Jan 4
O'Hare Intl. - Baltimore Washington Intl. Thurgood Marshall
$986
The price now is $765 per personFlight + Hotel
Tue, Dec 29 - Mon, Jan 4
O'Hare Intl. - Baltimore Washington Intl. Thurgood Marshall
$904
The price now is $733 per personFlight + Hotel
Mon, Dec 14 - Thu, Dec 17
O'Hare Intl. - Baltimore Washington Intl. Thurgood Marshall
$235
The price now is $192 per personFlight + Hotel
Tue, Dec 29 - Mon, Jan 4
O'Hare Intl. - Baltimore Washington Intl. Thurgood Marshall
$680
The price now is $562 per personFlight + Hotel
Fri, Dec 4 - Sun, Dec 6
Cincinnati - Northern Kentucky Intl. - Ronald Reagan Washington National
$313
The price now is $259 per personFlight + Hotel
Mon, Dec 14 - Thu, Dec 17
O'Hare Intl. - Baltimore Washington Intl. Thurgood Marshall
$280
The price now is $232 per personFlight + Hotel
Annapolis Vacation Packages 3-4 Night Stays
Mon, Dec 14 - Thu, Dec 17
O'Hare Intl. - Baltimore Washington Intl. Thurgood Marshall
$356
The price now is $243 per personFlight + Hotel
Mon, Dec 14 - Thu, Dec 17
O'Hare Intl. - Baltimore Washington Intl. Thurgood Marshall
$334
The price now is $241 per personFlight + Hotel
Mon, Dec 14 - Thu, Dec 17
O'Hare Intl. - Baltimore Washington Intl. Thurgood Marshall
$288
The price now is $209 per personFlight + Hotel
Fri, Dec 4 - Tue, Dec 8
O'Hare Intl. - Baltimore Washington Intl. Thurgood Marshall
$419
The price now is $313 per personFlight + Hotel
Fri, Dec 4 - Tue, Dec 8
O'Hare Intl. - Baltimore Washington Intl. Thurgood Marshall
$267
The price now is $200 per personFlight + Hotel
Mon, Dec 14 - Thu, Dec 17
O'Hare Intl. - Baltimore Washington Intl. Thurgood Marshall
$297
The price now is $226 per personFlight + Hotel
Mon, Dec 14 - Thu, Dec 17
O'Hare Intl. - Baltimore Washington Intl. Thurgood Marshall
$459
The price now is $360 per personFlight + Hotel
Mon, Dec 14 - Thu, Dec 17
O'Hare Intl. - Baltimore Washington Intl. Thurgood Marshall
$235
The price now is $192 per personFlight + Hotel
Tue, Dec 8 - Fri, Dec 11
O'Hare Intl. - Ronald Reagan Washington National
$395
The price now is $324 per personFlight + Hotel
Fri, Dec 4 - Tue, Dec 8
O'Hare Intl. - Baltimore Washington Intl. Thurgood Marshall
$280
The price now is $231 per personFlight + Hotel
Mon, Dec 14 - Thu, Dec 17
O'Hare Intl. - Baltimore Washington Intl. Thurgood Marshall
$280
The price now is $232 per personFlight + Hotel
Fri, Dec 4 - Tue, Dec 8
O'Hare Intl. - Baltimore Washington Intl. Thurgood Marshall
$745
The price now is $621 per personFlight + Hotel
Annapolis Vacation Packages 5-7 Night Stays
Tue, Dec 29 - Mon, Jan 4
O'Hare Intl. - Baltimore Washington Intl. Thurgood Marshall
$856
The price now is $590 per personFlight + Hotel
Tue, Dec 29 - Mon, Jan 4
O'Hare Intl. - Baltimore Washington Intl. Thurgood Marshall
$549
The price now is $383 per personFlight + Hotel
Tue, Dec 29 - Mon, Jan 4
O'Hare Intl. - Baltimore Washington Intl. Thurgood Marshall
$610
The price now is $434 per personFlight + Hotel
Tue, Dec 29 - Mon, Jan 4
O'Hare Intl. - Baltimore Washington Intl. Thurgood Marshall
$986
The price now is $765 per personFlight + Hotel
Tue, Dec 29 - Mon, Jan 4
O'Hare Intl. - Baltimore Washington Intl. Thurgood Marshall
$904
The price now is $733 per personFlight + Hotel
Fri, Dec 11 - Thu, Dec 17
Kansas City Intl. - Baltimore Washington Intl. Thurgood Marshall
$487
The price now is $401 per personFlight + Hotel
Tue, Dec 29 - Mon, Jan 4
O'Hare Intl. - Baltimore Washington Intl. Thurgood Marshall
$680
The price now is $562 per personFlight + Hotel
Tue, Dec 29 - Mon, Jan 4
O'Hare Intl. - Baltimore Washington Intl. Thurgood Marshall
$611
The price now is $505 per personFlight + Hotel
Tue, Dec 29 - Mon, Jan 4
O'Hare Intl. - Baltimore Washington Intl. Thurgood Marshall
$508
The price now is $421 per personFlight + Hotel
Fri, Dec 11 - Thu, Dec 17
Kansas City Intl. - Baltimore Washington Intl. Thurgood Marshall
$535
The price now is $445 per personFlight + Hotel
Tue, Dec 29 - Mon, Jan 4
O'Hare Intl. - Baltimore Washington Intl. Thurgood Marshall
$683
The price now is $568 per personFlight + Hotel
Fri, Dec 11 - Thu, Dec 17
Kansas City Intl. - Baltimore Washington Intl. Thurgood Marshall
$519
The price now is $440 per personFlight + Hotel
Last Minute Hotel Deals
Estimated price for 1 night/2 adults
Per night/room
Nov 1 - Nov 2
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Nov 4 - Nov 5
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Nov 3 - Nov 4
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Nov 20 - Nov 21
Per night/room
Nov 1 - Nov 2
Per night/room
Nov 1 - Nov 2
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Nov 18 - Nov 19
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Frequently Asked Questions About Annapolis
When is the best time of the year to find Annapolis vacation package deals?
is the best time to find cheap Annapolis vacation deals.
When are the high and low seasons for Annapolis vacations?
are the busiest months for Annapolis vacations, but have the smallest crowds.
Where can I find the best last minute vacation deals for Annapolis?
Only on Hotwire can you find last minute vacations from over 314 Annapolis destinations.
What if I have to cancel my trip to Annapolis?
The fastest path to canceling your booking is through one of our self-serve tools found at https://vacation.hotwire.com/lp/coronavirus-travel
Book your Annapolis Vacation
Other Hotels in Cities Near Annapolis
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Hotels in Neighborhoods Near Annapolis
- Historic District Hotels
- Arundel on the Bay Hotels
- Eastport Hotels
- West Annapolis Hotels
- Oyster Harbor Hotels
- Murray Hill Hotels
- Homewood Hotels
- Hunt Meadows Hotels
- Kingsport Hotels
- Anchorage Hotels
- Winchester-on-the-Severn Hotels
- Hillsmere Hotels
- Epping Forest Hotels
- Downs on the Severn Hotels
- Cape St. John Hotels
- Atlantis Hotels
Hotels Near Points of Interest in Annapolis
- Hotels near U.S. Naval Academy
- Hotels near Six Flags America
- Hotels near Westfield Annapolis Mall
- Hotels near Annapolis City Dock
- Hotels near Chesapeake Bay Bridge
- Hotels near Sandy Point State Park
- Hotels near Bowie State University
- Hotels near Anne Arundel Medical Center
- Hotels near Maryland State House
- Hotels near Navy-Marine Corps Memorial Stadium
- Hotels near Annapolis Harbour Center
- Hotels near Kunta Kinte–Alex Haley Memorial
- Hotels near Annapolis Maritime Museum
- Hotels near Allen Pond Park
- Hotels near Maryland Quiet Waters Park
- Hotels near St John's College
- Hotels near Bay Hills Golf Club
- Hotels near Maryland World War II Memorial
- Hotels near William Paca House
- Hotels near The Kunta Kinte Alex Haley Memorial