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    Exceptional! 5/5
    (7 reviews)
    avg/night
    • 3 BR
    • 2 BA
    • Sleeps 6
    House #759063vb
    7
    Viewed 6 times in the last 48 hours
      • 4 BR
      • 3 BA
      • Sleeps 8
      House #4487352
      3
      Viewed 5 times in the last 48 hours
        avg/night
        • 4 BR
        • 2 BA
        • 1 HF BA
        • Sleeps 8
        House #4558937
        1
        Viewed 5 times in the last 48 hours
          avg/night
          • 4 BR
          • 3 BA
          • Sleeps 8
          House #1054955vb
          Viewed 20 times in the last 48 hours
            avg/night
            • 1 BR
            • 1 BA
            • Sleeps 2
            Apartment #975033vb
            Viewed 18 times in the last 48 hours
              Exceptional! 5/5
              (58 reviews)
              avg/night
              • 3 BR
              • 3 BA
              • Sleeps 8
              House #294688vb
              58
              Viewed 49 times in the last 48 hours
                Wonderful! 4.9/5
                (13 reviews)
                avg/night
                • 1 BR
                • 1 BA
                • 1 HF BA
                • Sleeps 4
                Apartment #844031vb
                13
                Viewed 14 times in the last 48 hours
                  Exceptional! 5/5
                  (9 reviews)
                  avg/night
                  • 3 BR
                  • 2 BA
                  • Sleeps 8
                  Cottage #883977vb
                  9
                  Viewed 36 times in the last 48 hours
                    Wonderful! 4.8/5
                    (20 reviews)
                    avg/night
                    • 4 BR
                    • 3 BA
                    • Sleeps 12
                    House #3786046
                    20
                    Viewed 48 times in the last 48 hours
                      Wonderful! 4.9/5
                      (18 reviews)
                      avg/night
                      • 5 BR
                      • 4 BA
                      • Sleeps 18
                      House #581725vb
                      18
                      Viewed 27 times in the last 48 hours
                        Wonderful! 4.9/5
                        (11 reviews)
                        avg/night
                        • 3 BR
                        • 2 BA
                        • Sleeps 9
                        Apartment #409821vb
                        11
                        Viewed 23 times in the last 48 hours
                          Exceptional! 5/5
                          (25 reviews)
                          avg/night
                          • 2 BR
                          • 2 BA
                          • Sleeps 5
                          Cottage #608459vb
                          25
                          Viewed 34 times in the last 48 hours
                            Exceptional! 5/5
                            (41 reviews)
                            View details for price
                            • 4 BR
                            • 4 BA
                            • 1 HF BA
                            • Sleeps 13
                            House #356548vb
                            41
                            Viewed 9 times in the last 48 hours
                              Excellent! 4.7/5
                              (22 reviews)
                              avg/night
                              • 4 BR
                              • 2 BA
                              • Sleeps 10
                              House #704799vb
                              22
                              Viewed 18 times in the last 48 hours
                                Excellent! 4.6/5
                                (34 reviews)
                                avg/night
                                • 3 BR
                                • 1 BA
                                • 1 HF BA
                                • Sleeps 7
                                House #429782vb
                                34
                                Viewed 24 times in the last 48 hours
                                  Wonderful! 4.9/5
                                  (14 reviews)
                                  avg/night
                                  • 4 BR
                                  • 2 BA
                                  • Sleeps 10
                                  House #398147vb
                                  14
                                  Viewed 24 times in the last 48 hours
                                    Exceptional! 5/5
                                    (21 reviews)
                                    avg/night
                                    • 3 BR
                                    • 2 BA
                                    • 1 HF BA
                                    • Sleeps 8
                                    Cottage #503705vb
                                    21
                                    Viewed 15 times in the last 48 hours
                                      Excellent! 4.5/5
                                      (35 reviews)
                                      avg/night
                                      • 3 BR
                                      • 2 BA
                                      • Sleeps 12
                                      House #7002752
                                      35
                                      Viewed 53 times in the last 48 hours
                                        Wonderful! 4.9/5
                                        (34 reviews)
                                        avg/night
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 5
                                        Apartment #494798vb
                                        34
                                        Viewed 17 times in the last 48 hours
                                          Wonderful! 4.8/5
                                          (16 reviews)
                                          avg/night
                                          • 6 BR
                                          • 2 BA
                                          • Sleeps 11
                                          House #235930
                                          16
                                          Viewed 17 times in the last 48 hours
                                            Wonderful! 4.8/5
                                            (6 reviews)
                                            avg/night
                                            • 1 BR
                                            • 1 BA
                                            • Sleeps 5
                                            Apartment #838035vb
                                            6
                                            Viewed 20 times in the last 48 hours
                                              Wonderful! 4.8/5
                                              (11 reviews)
                                              avg/night
                                              • 3 BR
                                              • 1 BA
                                              • 1 HF BA
                                              • Sleeps 8
                                              House #571411vb
                                              11
                                              Viewed 13 times in the last 48 hours
                                                Exceptional! 5/5
                                                (6 reviews)
                                                avg/night
                                                • 2 BR
                                                • 1 BA
                                                • Sleeps 4
                                                Chateau / Country House #738311vb
                                                6
                                                Viewed 35 times in the last 48 hours
                                                  avg/night
                                                  • 3 BR
                                                  • 1 BA
                                                  • Sleeps 8
                                                  House #440251vb
                                                  3
                                                  Viewed 15 times in the last 48 hours
                                                    Wonderful! 4.9/5
                                                    (15 reviews)
                                                    avg/night
                                                    • 4 BR
                                                    • 2 BA
                                                    • Sleeps 8
                                                    Estate #730130vb
                                                    15
                                                    Viewed 70 times in the last 48 hours
                                                      Wonderful! 4.9/5
                                                      (8 reviews)
                                                      avg/night
                                                      • 3 BR
                                                      • 2 BA
                                                      • 1 HF BA
                                                      • Sleeps 8
                                                      House #797359vb
                                                      8
                                                      Viewed 40 times in the last 48 hours
                                                        Wonderful! 4.8/5
                                                        (5 reviews)
                                                        avg/night
                                                        • 1 BR
                                                        • 1 BA
                                                        • Sleeps 3
                                                        Apartment #589368vb
                                                        5
                                                        Viewed 24 times in the last 48 hours
                                                          • 5 BR
                                                          • 2 BA
                                                          • Sleeps 10
                                                          Farmhouse #623923vb
                                                          3
                                                          Viewed 20 times in the last 48 hours
                                                            • 4 BR
                                                            • 2 BA
                                                            • Sleeps 10
                                                            Farmhouse #598989vb
                                                            2
                                                            Viewed 15 times in the last 48 hours
                                                              Wonderful! 4.9/5
                                                              (9 reviews)
                                                              avg/night
                                                              • 4 BR
                                                              • 3 BA
                                                              • 1 HF BA
                                                              • Sleeps 8
                                                              House #458295vb
                                                              9
                                                              Viewed 16 times in the last 48 hours
                                                                Wonderful! 4.8/5
                                                                (29 reviews)
                                                                avg/night
                                                                • 2 BR
                                                                • 1 BA
                                                                • 1 HF BA
                                                                • Sleeps 6
                                                                House #431733vb
                                                                29
                                                                Viewed 21 times in the last 48 hours
                                                                  Wonderful! 4.8/5
                                                                  (19 reviews)
                                                                  avg/night
                                                                  • 4 BR
                                                                  • 4 BA
                                                                  • 1 HF BA
                                                                  • Sleeps 10
                                                                  Estate #606821vb
                                                                  19
                                                                  Viewed 38 times in the last 48 hours
                                                                    • 2 BR
                                                                    • 1 BA
                                                                    • Sleeps 4
                                                                    Apartment #1045032vb
                                                                    3
                                                                    Viewed 64 times in the last 48 hours
                                                                      Wonderful! 4.9/5
                                                                      (20 reviews)
                                                                      avg/night
                                                                      • 2 BR
                                                                      • 1 BA
                                                                      • Sleeps 6
                                                                      House #53282vb
                                                                      20
                                                                      Viewed 74 times in the last 48 hours
                                                                        Wonderful! 4.8/5
                                                                        (23 reviews)
                                                                        avg/night
                                                                        • 3 BR
                                                                        • 1 BA
                                                                        • Sleeps 6
                                                                        Cottage #418738vb
                                                                        23
                                                                        Viewed 24 times in the last 48 hours
                                                                          Wonderful! 4.9/5
                                                                          (10 reviews)
                                                                          avg/night
                                                                          • 5 BR
                                                                          • 2 BA
                                                                          • Sleeps 10
                                                                          Farmhouse #582873vb
                                                                          10
                                                                          Viewed 11 times in the last 48 hours
                                                                            • 4 BR
                                                                            • 2 BA
                                                                            • Sleeps 8
                                                                            House #3917327
                                                                            3
                                                                            Viewed 25 times in the last 48 hours
                                                                              Exceptional! 5/5
                                                                              (7 reviews)
                                                                              avg/night
                                                                              • 7 BR
                                                                              • 4 BA
                                                                              • 1 HF BA
                                                                              • Sleeps 13
                                                                              House #935769vb
                                                                              7
                                                                              Viewed 20 times in the last 48 hours
                                                                                Wonderful! 4.9/5
                                                                                (29 reviews)
                                                                                avg/night
                                                                                • 4 BR
                                                                                • 4 BA
                                                                                • Sleeps 8
                                                                                House #410328vb
                                                                                29
                                                                                Viewed 41 times in the last 48 hours
                                                                                  avg/night
                                                                                  • 8 BR
                                                                                  • 8 BA
                                                                                  • Sleeps 4
                                                                                  Hotel #4093884
                                                                                  Viewed 25 times in the last 48 hours
                                                                                    • 2 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 5
                                                                                    House #4112420
                                                                                    1
                                                                                    Viewed 5 times in the last 48 hours
                                                                                      avg/night
                                                                                      • 3 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 8
                                                                                      House #4204088
                                                                                      1
                                                                                      Viewed 6 times in the last 48 hours
                                                                                        Wonderful! 4.9/5
                                                                                        (20 reviews)
                                                                                        avg/night
                                                                                        • 4 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 8
                                                                                        Cottage #431105vb
                                                                                        20
                                                                                        Viewed 32 times in the last 48 hours
                                                                                          • 5 BR
                                                                                          • 5 BA
                                                                                          • 1 HF BA
                                                                                          • Sleeps 10
                                                                                          House #600779vb
                                                                                          3
                                                                                            avg/night
                                                                                            • Studio
                                                                                            • 1 BA
                                                                                            • Sleeps 2
                                                                                            House #4533503
                                                                                            Viewed 9 times in the last 48 hours
                                                                                              • 6 BR
                                                                                              • 4 BA
                                                                                              • 1 HF BA
                                                                                              • Sleeps 11
                                                                                              Estate #1015635vb
                                                                                              Viewed 6 times in the last 48 hours
                                                                                                • 4 BR
                                                                                                • 2 BA
                                                                                                • 1 HF BA
                                                                                                • Sleeps 11
                                                                                                House #592542vb
                                                                                                  avg/night
                                                                                                  • 1 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 2
                                                                                                  Guest House #1113002vb
                                                                                                  Viewed 7 times in the last 48 hours
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 6
                                                                                                    House #4247910
                                                                                                    Viewed 12 times in the last 48 hours
                                                                                                      • 4 BR
                                                                                                      • 4 BA
                                                                                                      • Sleeps 10
                                                                                                      House #732410vb
                                                                                                      Viewed 8 times in the last 48 hours

                                                                                                      Vacation Rentals in Chestertown, Maryland (63)