Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5
Start by selecting your hotel
Start by selecting your hotel
Start by selecting your hotel

Save up to $603 by booking Flight + Hotel.

Search 590,000 properties and 550 airlines worldwide.

Search over a million flights, hotels, packages, and more


Chestertown

Plan a vacation in Chestertown and check out its great range of attractions.

Packages in Chestertown

Get immediate savings when you purchase hotel and flight deals with Expedia. Many travelers understand that accommodation and flight packages are a wonderful way to preserve money and time. Just think of all the things you can do in Chestertown with the extra money.

Gain savings of up to $603 with a deal.

About 400 partner airlines and 321,000 hotels worldwide are ready for you to book via our enormous international database.

Expedia gives you some of the most competitive prices for your Eastern Chesapeake Shore travels.

You never have to worry about altering your group's plans, as we do not charge additional cancellation fees for almost all of our bookings.

Chestertown Vacation Packages

Guests in this area of Eastern Shore will be rubbing shoulders with approximately 5,000 residents.

Annapolis, the state capital, is about 25 miles to the southwest of Chestertown, and Worton is 5 miles to the north.

On a fine day, explore Wilmer Park, an inviting space where locals come to enjoy some time outdoors.

Stroll through the peaceful hallways and browse the artifacts and exhibits displayed at the Historical Society of Kent County Maryland.

One of the most iconic historic sites here is the Washington College. This atmospheric place offers visitors the chance to gain a greater understanding of the area's past.

There are some wonderful theater and dance institutes here. The most popular is the Garfield Center for the Arts at the Prince Theater. Before the performance, enjoy a pre-show meal at one of the nearby eateries.

Many tourists speak highly of their time at Rolphs Wharf Marina. The River Arts Chestertown is also worth thinking about.

Accommodation in Chestertown

Chestertown lodging options can be limited. Be sure to visit Expedia's booking website now to secure a spot.

Chestertown hotels include the Holiday Inn Express Hotel & Suites Chestertown and Quality Suites.


Top Hotel Deals

See all 104 Hotels in Chestertown
Holiday Inn Express Hotel & Suites Chestertown $85
Holiday Inn Express Hotel & Suites Chestertown

Holiday Inn Express Hotel & Suites Chestertown

150 Scheeler Road, Chestertown
     
    4.4
    of 5, from 239 reviews
    2.5 out of 5.0

    Situated in Chestertown, this hotel is 0.6 mi (0.9 km) from Washington College and 25.2 mi (40.5 km) from Queenstown Premium Outlets.

    John L Stam House $190
    John L Stam House

    John L Stam House

    114 Washington Ave, Chestertown
       
      4.8
      of 5, from 11 reviews
      3.0 out of 5.0

      Situated in Chestertown, this bed & breakfast is 0.5 mi (0.8 km) from Washington College and 24.1 mi (38.7 km) from Queenstown Premium Outlets.

      Driftwood Inn $59
      Driftwood Inn

      Driftwood Inn

      609 Washington Avenue, Chestertown
         
        1.9
        of 5, from 75 reviews
        2.0 out of 5.0

        Situated in Chestertown, this motel is 0.2 mi (0.4 km) from Washington College and 26.7 mi (42.9 km) from Queenstown Premium Outlets.

        Great Oak Manor $149
        Great Oak Manor

        Great Oak Manor

        10568 Cliff Rd, Chestertown
           
          4.2
          of 5, from 5 reviews
          3.5 out of 5.0

          Nestled on the beach, this Chestertown bed & breakfast is next to a golf course and 9.1 mi (14.6 km) from Washington College.

          Inn at Mitchell House $150
          Inn at Mitchell House

          Inn at Mitchell House

          8796 Maryland Pkwy, Chestertown
             
            5.0
            of 5, from 2 reviews
            3.0 out of 5.0

            Situated near the beach, this bed & breakfast is 11 mi (17.7 km) from Washington College.

            Quality Suites
            Quality Suites

            Quality Suites

            160 Scheeler Rd, Chestertown
               
              3.9
              of 5, from 104 reviews
              2.5 out of 5.0

              Situated in Chestertown, this hotel is 0.8 mi (1.4 km) from Washington College and 25.4 mi (40.9 km) from Queenstown Premium Outlets.

              Chester River Waterfront, Magnificent Views, Dock, Beach
              Chester River Waterfront, Magnificent Views, Dock, Beach

              Chester River Waterfront, Magnificent Views, Dock, Beach

              , Chestertown
                 
                4.5
                of 5, from 8 reviews
                0.0 out of 5.0

                Situated in Chestertown, this vacation home is close to Washington College. Regional attractions also include The Mainstay.

                Quit Guest Room to Stay in
                Quit Guest Room to Stay in

                Quit Guest Room to Stay in

                , Chestertown
                   
                  0.0 out of 5.0

                  Situated in Chestertown, this vacation home is close to Washington College.

                  Top Deals on Flights

                  These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.