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Most Frequently Booked Chestertown Hotels

Holiday Inn Express Hotel & Suites Chestertown C$119
Holiday Inn Express Hotel & Suites Chestertown

Holiday Inn Express Hotel & Suites Chestertown

150 Scheeler Road, Chestertown, MD
     
    4.7
    of 5, from 12 reviews
    2.5 out of 5.0 Stars

    Situated in Chestertown, this hotel is 0.6 mi (0.9 km) from Washington College and within 25 mi (40 km) of Rock Hall Harbor and Queenstown Premium Outlets. Queenstown Harbor Golf Club is 24.9 mi (40.1 km) away.

    Great Oak Manor C$260
    Great Oak Manor

    Great Oak Manor

    10568 Cliff Rd, Chestertown, MD
       
      4.0
      of 5, from 1 reviews
      3.5 out of 5.0 Stars

      Nestled on the beach, this Chestertown bed & breakfast is next to a golf course, 9.1 mi (14.6 km) from Washington College, and 12.6 mi (20.2 km) from Rock Hall Harbor.

      Inn at Mitchell House C$183
      Inn at Mitchell House

      Inn at Mitchell House

      8796 Maryland Pkwy, Chestertown, MD
         
        4.0
        of 5, from 1 reviews
        3.0 out of 5.0 Stars

        Situated near the beach, this bed & breakfast is 11 mi (17.6 km) from Washington College.

        Driftwood Inn C$91
        Driftwood Inn

        Driftwood Inn

        609 Washington Avenue, Chestertown, MD
           
          2.0
          of 5, from 2 reviews
          2.0 out of 5.0 Stars

          Situated in Chestertown, this motel is 0.2 mi (0.4 km) from Washington College and within 32 mi (52 km) of Rock Hall Harbor and Queenstown Harbor Golf Club. Queenstown Premium Outlets is 26.7 mi (42.9 km) away.

          Top Cheap Chestertown Hotel Deals

          Holiday Inn Express Hotel & Suites Chestertown C$119
          Holiday Inn Express Hotel & Suites Chestertown

          Holiday Inn Express Hotel & Suites Chestertown

          150 Scheeler Road, Chestertown, MD
             
            4.7
            of 5, from 12 reviews
            2.5 out of 5.0 Stars

            Situated in Chestertown, this hotel is 0.6 mi (0.9 km) from Washington College and within 25 mi (40 km) of Rock Hall Harbor and Queenstown Premium Outlets. Queenstown Harbor Golf Club is 24.9 mi (40.1 km) away.

            Driftwood Inn C$91
            Driftwood Inn

            Driftwood Inn

            609 Washington Avenue, Chestertown, MD
               
              2.0
              of 5, from 2 reviews
              2.0 out of 5.0 Stars

              Situated in Chestertown, this motel is 0.2 mi (0.4 km) from Washington College and within 32 mi (52 km) of Rock Hall Harbor and Queenstown Harbor Golf Club. Queenstown Premium Outlets is 26.7 mi (42.9 km) away.

              Top Luxury Chestertown Hotel Deals

              Driftwood Inn C$91
              Driftwood Inn

              Driftwood Inn

              609 Washington Avenue, Chestertown, MD
                 
                2.0
                of 5, from 2 reviews
                2.0 out of 5.0 Stars

                Situated in Chestertown, this motel is 0.2 mi (0.4 km) from Washington College and within 32 mi (52 km) of Rock Hall Harbor and Queenstown Harbor Golf Club. Queenstown Premium Outlets is 26.7 mi (42.9 km) away.

                Other Travelers Recently Booked These Chestertown Hotels

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                How Much is a Hotel Room in Chestertown?

                Hotels in Chestertown start at C$91 per night. Prices and availability subject to change. Additional terms may apply.

                Cheap Hotels in Chestertown

                Pack your bags—it’s time to embark on a getaway. Whether you’re craving a solo retreat or promising your family a vacation to remember, book one of the best hotels in Chestertown. These hotels are located within easy access of the city’s hottest attractions and entertainment, so you won’t miss a beat while you’re in town. Spend the days exploring the local landmarks and the evenings getting to know the nightlife. After exploring the city from top to bottom, rest up at a hotel that speaks to you. Find the perfect place that matches your trip’s vibe, from a trendy boutique to family-friendly accommodations.

                Allow us here at Travelocity to pair you with up Chestertown hotels that suit your vacation preferences. Discover places with convenient on-site restaurants, around-the-clock service, and pools where your kids can make a splash. Some hotels may boast fitness rooms and spa services, while others feature game rooms and Wi-Fi access. To top it all off, you’ll score cheap hotels in Chestertown that let you spend more on your activities and less on your lodging. Book and bundle your flight and hotel deals together today and save up to $537. It’s time to explore a new city, and break out of your routine.


                Recent Chestertown Hotel Reviews By Fellow Wanderers

                *Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.