Visit Annapolis and book a cheap hotel

Positioned between the big cities of Baltimore and Washington D.C., Annapolis, Maryland is an historic gem of the Chesapeake Bay.  Hundreds of quaint shops and restaurants line the brick red streets of Old Annapolis and dozens of sailboats bob in the harbor waters, making for a picturesque vacation spot.
 
Visit Annapolis before the summer ends and stay at the O’Callaghan Annapolis Hotel for rates starting at $104 a night, with savings up to 30 percent.  This hotel is located right in the city center, so you’ll have no problem finding all the historic sites and the best crab cakes. 

Book your stay through Hotels.com as soon as possible, and travel before Aug.31.  Discounts vary depending on length of stay, so be sure to read up on the terms and conditions before booking.

Save the sailing for when you get to Annapolis and book a flight to Maryland.  Accessible from two airports, you can book your flight to Washington D.C., or get on a flight to Baltimore.  Either way, we’ll help you find and save the most the money on all round-trip flights.

These deals and sample fares were priced at time of publish.  Prices may be subject to additional fees and taxes.

Atlanta flights to Baltimore from $135
Boston flights to Baltimore from $99
Chicago flights to Washington D.C. from $154
Detroit flights to Baltimore from $139
Indianapolis flights to Baltimore from $139
San Francisco flights to Baltimore from $219