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  • Showing 1-50 of 59
Additional fees apply. Taxes may be added.
    House #220506vb
    • 3 BR
    • 2 BA
    • Sleeps 6
    10

    Confirmation within 24 hours

    Your booking request will be confirmed or denied within 24 hours.

      House #759063vb
      • 3 BR
      • 2 BA
      • Sleeps 6
      7

      Confirmation within 24 hours

      Your booking request will be confirmed or denied within 24 hours.

        House #4252597
        • 3 BR
        • 1 BA
        • 1 HF BA
        • Sleeps 6
        1

        Confirmation within 24 hours

        Your booking request will be confirmed or denied within 24 hours.

          Townhome #688710vb
          • 2 BR
          • 2 BA
          • 1 HF BA
          • Sleeps 6
          2

          Confirmation within 24 hours

          Your booking request will be confirmed or denied within 24 hours.

            Apartment #975033vb
            • 1 BR
            • 1 BA
            • Sleeps 2

            Confirmation within 24 hours

            Your booking request will be confirmed or denied within 24 hours.

              House #294688vb
              • 3 BR
              • 3 BA
              • Sleeps 8
              41

              Confirmation within 24 hours

              Your booking request will be confirmed or denied within 24 hours.

                Apartment #844031vb
                • 1 BR
                • 1 BA
                • 1 HF BA
                • Sleeps 4
                6

                Confirmation within 24 hours

                Your booking request will be confirmed or denied within 24 hours.

                  House #704799vb
                  • 4 BR
                  • 2 BA
                  • Sleeps 10
                  15

                  Confirmation within 24 hours

                  Your booking request will be confirmed or denied within 24 hours.

                    Cottage #608459vb
                    • 2 BR
                    • 2 BA
                    • Sleeps 5
                    20

                    Confirmation within 24 hours

                    Your booking request will be confirmed or denied within 24 hours.

                      House #707088vb
                      • 2 BR
                      • 1 BA
                      • Sleeps 6
                      1

                      Confirmation within 24 hours

                      Your booking request will be confirmed or denied within 24 hours.

                        House #3786046
                        • 4 BR
                        • 3 BA
                        • Sleeps 12
                        13

                        Confirmation within 24 hours

                        Your booking request will be confirmed or denied within 24 hours.

                          Cottage #503705vb
                          • 3 BR
                          • 2 BA
                          • 1 HF BA
                          • Sleeps 8
                          17

                          Confirmation within 24 hours

                          Your booking request will be confirmed or denied within 24 hours.

                            Apartment #409821vb
                            • 3 BR
                            • 2 BA
                            • Sleeps 9
                            10

                            Confirmation within 24 hours

                            Your booking request will be confirmed or denied within 24 hours.

                              Apartment #494798vb
                              • 1 BR
                              • 1 BA
                              • Sleeps 5
                              30

                              Confirmation within 24 hours

                              Your booking request will be confirmed or denied within 24 hours.

                                House #7002752
                                • 3 BR
                                • 2 BA
                                • Sleeps 12
                                30

                                Confirmation within 24 hours

                                Your booking request will be confirmed or denied within 24 hours.

                                  House #356548vb
                                  • 4 BR
                                  • 4 BA
                                  • 1 HF BA
                                  • Sleeps 13
                                  40

                                  Confirmation within 24 hours

                                  Your booking request will be confirmed or denied within 24 hours.

                                    House #398147vb
                                    • 4 BR
                                    • 2 BA
                                    • Sleeps 10
                                    10

                                    Confirmation within 24 hours

                                    Your booking request will be confirmed or denied within 24 hours.

                                      House #4112420
                                      • 2 BR
                                      • 1 BA
                                      • Sleeps 5
                                      1

                                      Instant confirmation

                                      Your booking request will be confirmed immediately.

                                        House #431733vb
                                        • 2 BR
                                        • 1 BA
                                        • 1 HF BA
                                        • Sleeps 6
                                        25

                                        Confirmation within 24 hours

                                        Your booking request will be confirmed or denied within 24 hours.

                                          House #706116vb
                                          • 3 BR
                                          • 2 BA
                                          • Sleeps 9
                                          9

                                          Confirmation within 24 hours

                                          Your booking request will be confirmed or denied within 24 hours.

                                            House #797359vb
                                            • 3 BR
                                            • 2 BA
                                            • 1 HF BA
                                            • Sleeps 8
                                            3

                                            Confirmation within 24 hours

                                            Your booking request will be confirmed or denied within 24 hours.

                                              House #235930
                                              • 6 BR
                                              • 2 BA
                                              • Sleeps 11
                                              13

                                              Confirmation within 24 hours

                                              Your booking request will be confirmed or denied within 24 hours.

                                                Estate #730130vb
                                                • 4 BR
                                                • 2 BA
                                                • Sleeps 8
                                                12

                                                Confirmation within 24 hours

                                                Your booking request will be confirmed or denied within 24 hours.

                                                  Farmhouse #598989vb
                                                  • 4 BR
                                                  • 2 BA
                                                  • Sleeps 10
                                                  2

                                                  Confirmation within 24 hours

                                                  Your booking request will be confirmed or denied within 24 hours.

                                                    House #571411vb
                                                    • 3 BR
                                                    • 1 BA
                                                    • 1 HF BA
                                                    • Sleeps 8
                                                    10

                                                    Confirmation within 24 hours

                                                    Your booking request will be confirmed or denied within 24 hours.

                                                      Farmhouse #582873vb
                                                      • 5 BR
                                                      • 2 BA
                                                      • Sleeps 10
                                                      8

                                                      Confirmation within 24 hours

                                                      Your booking request will be confirmed or denied within 24 hours.

                                                        House #429782vb
                                                        • 3 BR
                                                        • 1 BA
                                                        • 1 HF BA
                                                        • Sleeps 7
                                                        29

                                                        Confirmation within 24 hours

                                                        Your booking request will be confirmed or denied within 24 hours.

                                                          House #726629vb
                                                          • 5 BR
                                                          • 3 BA
                                                          • Sleeps 8
                                                          5

                                                          Confirmation within 24 hours

                                                          Your booking request will be confirmed or denied within 24 hours.

                                                            House #53282vb
                                                            • 2 BR
                                                            • 1 BA
                                                            • Sleeps 6
                                                            18

                                                            Confirmation within 24 hours

                                                            Your booking request will be confirmed or denied within 24 hours.

                                                              Estate #606821vb
                                                              • 4 BR
                                                              • 4 BA
                                                              • 1 HF BA
                                                              • Sleeps 10
                                                              18

                                                              Confirmation within 24 hours

                                                              Your booking request will be confirmed or denied within 24 hours.

                                                                Chateau / Country House #738311vb
                                                                • 2 BR
                                                                • 1 BA
                                                                • Sleeps 4
                                                                4

                                                                Confirmation within 24 hours

                                                                Your booking request will be confirmed or denied within 24 hours.

                                                                  Cottage #418738vb
                                                                  • 3 BR
                                                                  • 1 BA
                                                                  • Sleeps 6
                                                                  22

                                                                  Confirmation within 24 hours

                                                                  Your booking request will be confirmed or denied within 24 hours.

                                                                    Apartment #589368vb
                                                                    • 1 BR
                                                                    • 1 BA
                                                                    • Sleeps 3
                                                                    3

                                                                    Confirmation within 24 hours

                                                                    Your booking request will be confirmed or denied within 24 hours.

                                                                      House #458295vb
                                                                      • 4 BR
                                                                      • 3 BA
                                                                      • 1 HF BA
                                                                      • Sleeps 8
                                                                      8

                                                                      Confirmation within 24 hours

                                                                      Your booking request will be confirmed or denied within 24 hours.

                                                                        House #565548vb
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 8
                                                                        3

                                                                        Confirmation within 24 hours

                                                                        Your booking request will be confirmed or denied within 24 hours.

                                                                          House #3917327
                                                                          • 4 BR
                                                                          • 2 BA
                                                                          • Sleeps 8

                                                                          Confirmation within 24 hours

                                                                          Your booking request will be confirmed or denied within 24 hours.

                                                                            House #592542vb
                                                                            • 4 BR
                                                                            • 2 BA
                                                                            • 1 HF BA
                                                                            • Sleeps 11

                                                                            Confirmation within 24 hours

                                                                            Your booking request will be confirmed or denied within 24 hours.

                                                                              House #4204088
                                                                              • 3 BR
                                                                              • 1 BA
                                                                              • Sleeps 8
                                                                              1

                                                                              Confirmation within 24 hours

                                                                              Your booking request will be confirmed or denied within 24 hours.

                                                                                Cottage #883977vb
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Sleeps 8

                                                                                Confirmation within 24 hours

                                                                                Your booking request will be confirmed or denied within 24 hours.

                                                                                  House #473897vb
                                                                                  • 2 BR
                                                                                  • 1 BA
                                                                                  • 1 HF BA
                                                                                  • Sleeps 4
                                                                                  9

                                                                                  Confirmation within 24 hours

                                                                                  Your booking request will be confirmed or denied within 24 hours.

                                                                                    House #600779vb
                                                                                    • 5 BR
                                                                                    • 5 BA
                                                                                    • 1 HF BA
                                                                                    • Sleeps 10
                                                                                    3

                                                                                    Confirmation within 24 hours

                                                                                    Your booking request will be confirmed or denied within 24 hours.

                                                                                      House #440251vb
                                                                                      • 3 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 8
                                                                                      1

                                                                                      Confirmation within 24 hours

                                                                                      Your booking request will be confirmed or denied within 24 hours.

                                                                                        Hotel #4093884
                                                                                        • 8 BR
                                                                                        • 8 BA
                                                                                        • Sleeps 4

                                                                                        Confirmation within 24 hours

                                                                                        Your booking request will be confirmed or denied within 24 hours.

                                                                                          House #912542vb
                                                                                          • 5 BR
                                                                                          • 4 BA
                                                                                          • Sleeps 11

                                                                                          Confirmation within 24 hours

                                                                                          Your booking request will be confirmed or denied within 24 hours.

                                                                                            House #732410vb
                                                                                            • 4 BR
                                                                                            • 4 BA
                                                                                            • Sleeps 10

                                                                                            Confirmation within 24 hours

                                                                                            Your booking request will be confirmed or denied within 24 hours.

                                                                                              House #4176971
                                                                                              • 4 BR
                                                                                              • 4 BA
                                                                                              • Sleeps 8

                                                                                              Confirmation within 24 hours

                                                                                              Your booking request will be confirmed or denied within 24 hours.

                                                                                                House #935769vb
                                                                                                • 7 BR
                                                                                                • 4 BA
                                                                                                • 1 HF BA
                                                                                                • Sleeps 13
                                                                                                4

                                                                                                Confirmation within 24 hours

                                                                                                Your booking request will be confirmed or denied within 24 hours.

                                                                                                  Recreational Vehicle #4243662
                                                                                                  • 1 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 10

                                                                                                  Confirmation within 24 hours

                                                                                                  Your booking request will be confirmed or denied within 24 hours.

                                                                                                    House #395841vb
                                                                                                    • 4 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 12
                                                                                                    19

                                                                                                    Confirmation within 24 hours

                                                                                                    Your booking request will be confirmed or denied within 24 hours.

                                                                                                      Estate #4200107
                                                                                                      • 6 BR
                                                                                                      • 4 BA
                                                                                                      • Sleeps 14
                                                                                                      1

                                                                                                      Confirmation within 24 hours

                                                                                                      Your booking request will be confirmed or denied within 24 hours.

                                                                                                      • 1 - 50 of 59

                                                                                                      Chestertown Vacation Rentals (59)