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  • Showing 1-50 of 300+
Additional fees apply. Taxes may be added.
    Condo #3804012
    • 2 BR
    • 1 BA
    • Sleeps 5
    6

    Confirmation within 24 hours

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

      Cottage #175549
      • 3 BR
      • 3 BA
      • Sleeps 8
      8

      Confirmation within 24 hours

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

        House #4240841
        • 4 BR
        • 2 BA
        • Sleeps 12
        10

        Confirmation within 24 hours

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

          House #4044539
          • 2 BR
          • 2 BA
          • Sleeps 4
          10

          Confirmation within 24 hours

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

            Condo #3896538
            • 1 BR
            • 1 BA
            • Sleeps 6
            11

            Confirmation within 24 hours

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

              Condo #716031vb
              • 2 BR
              • 1 BA
              • Sleeps 6
              14

              Confirmation within 24 hours

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

                Cabin #641786vb
                • 2 BR
                • 2 BA
                • 1 HF BA
                • Sleeps 8
                14

                Confirmation within 24 hours

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

                  House #4073769
                  • 3 BR
                  • 2 BA
                  • Sleeps 8
                  15

                  Confirmation within 24 hours

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

                    House #7080936
                    • 3 BR
                    • 1 BA
                    • Sleeps 8
                    13

                    Confirmation within 24 hours

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

                      Condo #4014526
                      • 3 BR
                      • 3 BA
                      • Sleeps 6
                      8

                      Confirmation within 24 hours

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

                        Cottage #3496194
                        • 4 BR
                        • 1 BA
                        • Sleeps 7
                        9

                        Confirmation within 24 hours

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

                          Townhome #978720
                          • 3 BR
                          • 2 BA
                          • 1 HF BA
                          • Sleeps 8
                          13

                          Confirmation within 24 hours

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

                            House #876933vb
                            • 4 BR
                            • 2 BA
                            • Sleeps 10
                            5

                            Confirmation within 24 hours

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

                              Cabin #3014265
                              • 2 BR
                              • 1 BA
                              • Sleeps 6
                              17

                              Confirmation within 24 hours

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

                                Cottage #3828287
                                • 2 BR
                                • 1 BA
                                • 1 HF BA
                                • Sleeps 7
                                8

                                Confirmation within 24 hours

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

                                  Cabin #3016070
                                  • 2 BR
                                  • 1 BA
                                  • Sleeps 5
                                  5

                                  Confirmation within 24 hours

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

                                    Townhome #689905vb
                                    • 3 BR
                                    • 3 BA
                                    • Sleeps 7
                                    6

                                    Confirmation within 24 hours

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

                                      House #3924952
                                      • 3 BR
                                      • 2 BA
                                      • Sleeps 10
                                      6

                                      Confirmation within 24 hours

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

                                        Cottage #3667204
                                        • 4 BR
                                        • 1 BA
                                        • Sleeps 7
                                        1

                                        Confirmation within 24 hours

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

                                          House #258920
                                          • 6 BR
                                          • 3 BA
                                          • Sleeps 20
                                          13

                                          Confirmation within 24 hours

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

                                            House #4313390
                                            • 3 BR
                                            • 2 BA
                                            • Sleeps 9
                                            0

                                            Confirmation within 24 hours

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

                                              Chalet #593993vb
                                              • 4 BR
                                              • 2 BA
                                              • 1 HF BA
                                              • Sleeps 8
                                              0

                                              Confirmation within 24 hours

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

                                                Lodge #3727616
                                                • 6 BR
                                                • 2 BA
                                                • Sleeps 11
                                                1

                                                Confirmation within 24 hours

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

                                                  House #239560
                                                  • 5 BR
                                                  • 2 BA
                                                  • Sleeps 8
                                                  0

                                                  Confirmation within 24 hours

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

                                                    Apartment #948565vb
                                                    • 2 BR
                                                    • 1 BA
                                                    • Sleeps 6
                                                    0

                                                    Confirmation within 24 hours

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

                                                      House #948569vb
                                                      • 4 BR
                                                      • 2 BA
                                                      • Sleeps 13
                                                      0

                                                      Confirmation within 24 hours

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

                                                        Apartment #3726412
                                                        • 4 BR
                                                        • 4 BA
                                                        • 1 HF BA
                                                        • Sleeps 16
                                                        1

                                                        Confirmation within 24 hours

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

                                                          House #557834vb
                                                          • 6 BR
                                                          • 3 BA
                                                          • Sleeps 12
                                                          1

                                                          Confirmation within 24 hours

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

                                                            Cabin #4222462
                                                            • 2 BR
                                                            • 2 BA
                                                            • Sleeps 8
                                                            0

                                                            Confirmation within 24 hours

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

                                                              Cabin #7006524
                                                              • 2 BR
                                                              • 1 BA
                                                              • Sleeps 5
                                                              8

                                                              Confirmation within 24 hours

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

                                                                House #387688vb
                                                                • 3 BR
                                                                • 2 BA
                                                                • Sleeps 10
                                                                0

                                                                Confirmation within 24 hours

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

                                                                Instant confirmation

                                                                Your booking request will be confirmed immediately.

                                                                  Cabin #4277500
                                                                  • 3 BR
                                                                  • 2 BA
                                                                  • Sleeps 6
                                                                  1

                                                                  Confirmation within 24 hours

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

                                                                    Lodge #955694vb
                                                                    • 8 BR
                                                                    • 9 BA
                                                                    • Sleeps 18
                                                                    0

                                                                    Confirmation within 24 hours

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

                                                                      House #622903vb
                                                                      • 3 BR
                                                                      • 3 BA
                                                                      • Sleeps 8
                                                                      3

                                                                      Confirmation within 24 hours

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

                                                                        House #4084910
                                                                        • 2 BR
                                                                        • 1 BA
                                                                        • Sleeps 4
                                                                        2

                                                                        Confirmation within 24 hours

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

                                                                          House #914537vb
                                                                          • 5 BR
                                                                          • 3 BA
                                                                          • 1 HF BA
                                                                          • Sleeps 14
                                                                          1

                                                                          Confirmation within 24 hours

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

                                                                            House #784245vb
                                                                            • 4 BR
                                                                            • 4 BA
                                                                            • Sleeps 13
                                                                            5

                                                                            Confirmation within 24 hours

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

                                                                              House #7083768
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 8
                                                                              1

                                                                              Confirmation within 24 hours

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

                                                                                House #4154905
                                                                                • 4 BR
                                                                                • 3 BA
                                                                                • Sleeps 14
                                                                                3

                                                                                Confirmation within 24 hours

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

                                                                                  Lodge #3022139
                                                                                  • 8 BR
                                                                                  • 2 BA
                                                                                  • 1 HF BA
                                                                                  • Sleeps 16
                                                                                  17

                                                                                  Confirmation within 24 hours

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

                                                                                    House #962469vb
                                                                                    • 4 BR
                                                                                    • 3 BA
                                                                                    • Sleeps 12
                                                                                    2

                                                                                    Confirmation within 24 hours

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

                                                                                      Chalet #367276vb
                                                                                      • 3 BR
                                                                                      • 1 BA
                                                                                      • 1 HF BA
                                                                                      • Sleeps 8
                                                                                      24

                                                                                      Confirmation within 24 hours

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

                                                                                        House #781031vb
                                                                                        • 6 BR
                                                                                        • 4 BA
                                                                                        • Sleeps 18
                                                                                        5

                                                                                        Confirmation within 24 hours

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

                                                                                          House #716522vb
                                                                                          • 4 BR
                                                                                          • 3 BA
                                                                                          • 1 HF BA
                                                                                          • Sleeps 12
                                                                                          19

                                                                                          Confirmation within 24 hours

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

                                                                                            House #189443
                                                                                            • 5 BR
                                                                                            • 3 BA
                                                                                            • Sleeps 12
                                                                                            14

                                                                                            Confirmation within 24 hours

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

                                                                                              House #4208239
                                                                                              • 4 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 7
                                                                                              3

                                                                                              Confirmation within 24 hours

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

                                                                                                House #423420vb
                                                                                                • 3 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 10
                                                                                                46

                                                                                                Confirmation within 24 hours

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

                                                                                                  Cottage #338616
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 8
                                                                                                  14

                                                                                                  Confirmation within 24 hours

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

                                                                                                    Apartment #270837
                                                                                                    • 2 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 4
                                                                                                    2

                                                                                                    Confirmation within 24 hours

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

                                                                                                    • 1 - 50 of 300+

                                                                                                    Chestertown Vacation Rentals (300+)