Vacations in Annapolis
2 travelers
KAYAK searches hundreds of travel sites at once for vacation package deals in Annapolis
...and more
Here is why travelers choose KAYAK
Free to useThere are no hidden charges or fees.
Filter your dealsFilter by free cancellation, free breakfast and more.
Millions of reviewsCheck ratings based on millions of real guest reviews.
Bundle and saveSave money when you bundle your flight + hotel.
Cheap Annapolis package deals
Discover the best prices by selecting your travel dates on KAYAK.
Most popular Annapolis flight and hotel deals
Show allFree Wi-Fi
Pool
Pet friendly
Chicago O'Hare Intl
Breakfast
3 nights + flight
$393
Downtown
Free Wi-Fi
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$532
Parking
Free Wi-Fi
Pool
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$428
1313 West Luxury Boutique Hotel - Annapolis - Living room![1313 West Luxury Boutique Hotel - Annapolis - Living room]()
1313 West Luxury Boutique Hotel
Parking
Free Wi-Fi
Chicago O'Hare Intl
Meals not included
3 nights + flight
$1,163
Lighthouse Inn - Annapolis - Living room![Lighthouse Inn - Annapolis - Living room]()
Lighthouse Inn
Parking
Free Wi-Fi
Chicago O'Hare Intl
Meals not included
3 nights + flight
$2,192
Parking
Free Wi-Fi
Pool
Chicago O'Hare Intl
Meals not included
3 nights + flight
$367
Fairfield by Marriott Inn & Suites Annapolis - Annapolis - Building![Fairfield by Marriott Inn & Suites Annapolis - Annapolis - Building]()
Fairfield by Marriott Inn & Suites Annapolis
Free Wi-Fi
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$426
Residence Inn by Marriott Annapolis - Annapolis - Bedroom![Residence Inn by Marriott Annapolis - Annapolis - Bedroom]()
Residence Inn by Marriott Annapolis
Free Wi-Fi
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$498
Parking
Free Wi-Fi
Chicago O'Hare Intl
Breakfast
3 nights + flight
$406
Free Wi-Fi
Pet friendly
Chicago O'Hare Intl
Breakfast
3 nights + flight
$347
Free Wi-Fi
Pool
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$574
Gatehouse Annapolis - Annapolis - Living room![Gatehouse Annapolis - Annapolis - Living room]()
Gatehouse Annapolis
Parking
Free Wi-Fi
Chicago O'Hare Intl
Meals not included
3 nights + flight
$2,233
Downtown
Free Wi-Fi
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$426
When to book a vacation in Annapolis
Price includes flights and 3 nights accommodation for 2 travelers. Prices are not fixed and may vary with time.
Tips for finding Annapolis package deals
- There are loads of types of vacations in Annapolis and the cost will depend on what type of trip you’re taking and for how long you’d like to stay. Here are the latest prices for a 3 night trip for 2 travelers: Top vacation $562; Family vacation $562.
Where to stay in Annapolis
Our map will help you find the perfect place to stay for your vacation in Annapolis by showing you the exact location of each hotel.
Everything you need to know for your vacation in Annapolis
Complete your trip to Annapolis
Annapolis vacation information
| Top vacation (Flight+Hotel) | $562 |
|---|---|
| Family vacation (Flight+Hotel) | $562 |