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  • Showing 1-50 of 300+
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    Excellent! 4.4/5
    (11 reviews)
    $91
    avg/night
    Condo #3896538
    • 1 BR
    • 1 BA
    • Sleeps 6
    11
    Viewed 29 times in the last 48 hours

    Confirmation within 24 hours

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

      Wonderful! 4.9/5
      (8 reviews)
      avg/night
      Cottage #175549
      • 3 BR
      • 3 BA
      • Sleeps 8
      8
      Viewed 42 times in the last 48 hours

      Confirmation within 24 hours

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

        Wonderful! 4.9/5
        (14 reviews)
        avg/night
        Condo #716031vb
        • 2 BR
        • 1 BA
        • Sleeps 6
        14
        Viewed 30 times in the last 48 hours

        Confirmation within 24 hours

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

          Wonderful! 4.8/5
          (11 reviews)
          avg/night
          House #4240841
          • 4 BR
          • 2 BA
          • Sleeps 12
          11
          Viewed 41 times in the last 48 hours

          Confirmation within 24 hours

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

            Very Good! 4.2/5
            (6 reviews)
            avg/night
            Condo #3804012
            • 2 BR
            • 1 BA
            • Sleeps 5
            6
            Viewed 21 times in the last 48 hours

            Confirmation within 24 hours

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

              Wonderful! 4.9/5
              (12 reviews)
              avg/night
              House #4044539
              • 2 BR
              • 2 BA
              • Sleeps 4
              12
              Viewed 33 times in the last 48 hours

              Confirmation within 24 hours

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

                Exceptional! 5/5
                (6 reviews)
                avg/night
                Townhome #689905vb
                • 3 BR
                • 3 BA
                • Sleeps 7
                6
                Viewed 28 times in the last 48 hours

                Confirmation within 24 hours

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

                  Excellent! 4.3/5
                  (17 reviews)
                  avg/night
                  Cabin #3014265
                  • 2 BR
                  • 1 BA
                  • Sleeps 6
                  17
                  Viewed 35 times in the last 48 hours

                  Confirmation within 24 hours

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

                    Exceptional! 5/5
                    (5 reviews)
                    avg/night
                    House #876933vb
                    • 4 BR
                    • 2 BA
                    • Sleeps 10
                    5
                    Viewed 31 times in the last 48 hours

                    Confirmation within 24 hours

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

                      Very Good! 4/5
                      (9 reviews)
                      avg/night
                      Condo #4014526
                      • 3 BR
                      • 3 BA
                      • Sleeps 6
                      9
                      Viewed 40 times in the last 48 hours

                      Confirmation within 24 hours

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

                        Exceptional! 5/5
                        (6 reviews)
                        avg/night
                        House #3924952
                        • 3 BR
                        • 2 BA
                        • Sleeps 10
                        6
                        Viewed 76 times in the last 48 hours

                        Confirmation within 24 hours

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

                          Excellent! 4.5/5
                          (8 reviews)
                          avg/night
                          Cottage #3828287
                          • 2 BR
                          • 1 BA
                          • 1 HF BA
                          • Sleeps 7
                          8
                          Viewed 24 times in the last 48 hours

                          Confirmation within 24 hours

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

                            Good! 3.8/5
                            (5 reviews)
                            avg/night
                            Cabin #3016070
                            • 2 BR
                            • 1 BA
                            • Sleeps 5
                            5
                            Viewed 38 times in the last 48 hours

                            Confirmation within 24 hours

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

                              Wonderful! 4.9/5
                              (15 reviews)
                              avg/night
                              House #4073769
                              • 3 BR
                              • 2 BA
                              • Sleeps 8
                              15
                              Viewed 11 times in the last 48 hours

                              Confirmation within 24 hours

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

                                Excellent! 4.6/5
                                (16 reviews)
                                avg/night
                                Cabin #641786vb
                                • 2 BR
                                • 2 BA
                                • 1 HF BA
                                • Sleeps 8
                                16
                                Viewed 13 times in the last 48 hours

                                Confirmation within 24 hours

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

                                  Excellent! 4.3/5
                                  (13 reviews)
                                  avg/night
                                  House #258920
                                  • 6 BR
                                  • 3 BA
                                  • Sleeps 26
                                  13
                                  Viewed 74 times in the last 48 hours

                                  Confirmation within 24 hours

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

                                    Wonderful! 4.9/5
                                    (16 reviews)
                                    avg/night
                                    House #7080936
                                    • 3 BR
                                    • 1 BA
                                    • Sleeps 8
                                    16
                                    Viewed 19 times in the last 48 hours

                                    Instant confirmation

                                    Your booking request will be confirmed immediately.

                                      House #4313390
                                      • 3 BR
                                      • 2 BA
                                      • Sleeps 9
                                      Viewed 36 times in the last 48 hours

                                      Confirmation within 24 hours

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

                                        Exceptional! 5/5
                                        (9 reviews)
                                        avg/night
                                        Cottage #3496194
                                        • 4 BR
                                        • 1 BA
                                        • Sleeps 7
                                        9
                                        Viewed 16 times in the last 48 hours

                                        Confirmation within 24 hours

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

                                          avg/night
                                          Chalet #593993vb
                                          • 4 BR
                                          • 2 BA
                                          • 1 HF BA
                                          • Sleeps 8
                                          Viewed 16 times in the last 48 hours

                                          Confirmation within 24 hours

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

                                            House #557834vb
                                            • 6 BR
                                            • 3 BA
                                            • Sleeps 12
                                            1
                                            Viewed 38 times in the last 48 hours

                                            Confirmation within 24 hours

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

                                              $95
                                              avg/night
                                              Apartment #948565vb
                                              • 2 BR
                                              • 1 BA
                                              • Sleeps 6
                                              Viewed 13 times in the last 48 hours

                                              Instant confirmation

                                              Your booking request will be confirmed immediately.

                                                avg/night
                                                Cottage #3667204
                                                • 4 BR
                                                • 1 BA
                                                • Sleeps 7
                                                1
                                                Viewed 17 times in the last 48 hours

                                                Confirmation within 24 hours

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

                                                  avg/night
                                                  Lodge #3727616
                                                  • 6 BR
                                                  • 2 BA
                                                  • Sleeps 11
                                                  1
                                                  Viewed 14 times in the last 48 hours

                                                  Confirmation within 24 hours

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

                                                    avg/night
                                                    House #948569vb
                                                    • 4 BR
                                                    • 2 BA
                                                    • Sleeps 13
                                                    Viewed 53 times in the last 48 hours

                                                    Instant confirmation

                                                    Your booking request will be confirmed immediately.

                                                      House #239560
                                                      • 5 BR
                                                      • 2 BA
                                                      • Sleeps 8
                                                      Viewed 18 times in the last 48 hours

                                                      Confirmation within 24 hours

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

                                                        avg/night
                                                        Cottage #1020543vb
                                                        • 4 BR
                                                        • 2 BA
                                                        • Sleeps 8
                                                        Viewed 36 times in the last 48 hours

                                                        Confirmation within 24 hours

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

                                                          avg/night
                                                          Cabin #1021229vb
                                                          • 1 BR
                                                          • 1 BA
                                                          • Sleeps 2
                                                          Viewed 7 times in the last 48 hours

                                                          Confirmation within 24 hours

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

                                                            Wonderful! 4.9/5
                                                            (14 reviews)
                                                            avg/night
                                                            Townhome #978720
                                                            • 3 BR
                                                            • 2 BA
                                                            • 1 HF BA
                                                            • Sleeps 8
                                                            14
                                                            Viewed 81 times in the last 48 hours

                                                            Confirmation within 24 hours

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

                                                              avg/night
                                                              Apartment #3726412
                                                              • 4 BR
                                                              • 4 BA
                                                              • 1 HF BA
                                                              • Sleeps 16
                                                              1
                                                              Viewed 44 times in the last 48 hours

                                                              Confirmation within 24 hours

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

                                                                avg/night
                                                                Cabin #4087680
                                                                • 2 BR
                                                                • 2 BA
                                                                • Sleeps 6
                                                                Viewed 27 times in the last 48 hours

                                                                Confirmation within 24 hours

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

                                                                  avg/night
                                                                  Cabin #4222462
                                                                  • 2 BR
                                                                  • 2 BA
                                                                  • Sleeps 8
                                                                  Viewed 15 times in the last 48 hours

                                                                  Confirmation within 24 hours

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

                                                                    Wonderful! 4.9/5
                                                                    (67 reviews)
                                                                    avg/night
                                                                    House #179508
                                                                    • 5 BR
                                                                    • 3 BA
                                                                    • 1 HF BA
                                                                    • Sleeps 16
                                                                    67
                                                                    Viewed 121 times in the last 48 hours

                                                                    Confirmation within 24 hours

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

                                                                      Exceptional! 5/5
                                                                      (96 reviews)
                                                                      avg/night
                                                                      House #3001286
                                                                      • 7 BR
                                                                      • 6 BA
                                                                      • 1 HF BA
                                                                      • Sleeps 18
                                                                      96
                                                                      Viewed 290 times in the last 48 hours

                                                                      Confirmation within 24 hours

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

                                                                        Wonderful! 4.9/5
                                                                        (33 reviews)
                                                                        avg/night
                                                                        House #3876403
                                                                        • 6 BR
                                                                        • 3 BA
                                                                        • 2 HF BA
                                                                        • Sleeps 15
                                                                        33
                                                                        Viewed 62 times in the last 48 hours

                                                                        Confirmation within 24 hours

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

                                                                          Wonderful! 4.9/5
                                                                          (10 reviews)
                                                                          avg/night
                                                                          House #863326vb
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • Sleeps 7
                                                                          10
                                                                          Viewed 72 times in the last 48 hours

                                                                          Confirmation within 24 hours

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

                                                                            Wonderful! 4.9/5
                                                                            (11 reviews)
                                                                            avg/night
                                                                            Cabin #802195vb
                                                                            • 2 BR
                                                                            • 1 BA
                                                                            • Sleeps 6
                                                                            11
                                                                            Viewed 70 times in the last 48 hours

                                                                            Confirmation within 24 hours

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

                                                                              Excellent! 4.5/5
                                                                              (6 reviews)
                                                                              avg/night
                                                                              House #720321vb
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 8
                                                                              6
                                                                              Viewed 82 times in the last 48 hours

                                                                              Confirmation within 24 hours

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

                                                                                Exceptional! 5/5
                                                                                (25 reviews)
                                                                                avg/night
                                                                                House #3540173
                                                                                • 5 BR
                                                                                • 4 BA
                                                                                • 1 HF BA
                                                                                • Sleeps 12
                                                                                25
                                                                                Viewed 68 times in the last 48 hours

                                                                                Confirmation within 24 hours

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

                                                                                  Wonderful! 4.9/5
                                                                                  (46 reviews)
                                                                                  avg/night
                                                                                  House #423420vb
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 10
                                                                                  46
                                                                                  Viewed 61 times in the last 48 hours

                                                                                  Confirmation within 24 hours

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

                                                                                    Very Good! 4.2/5
                                                                                    (12 reviews)
                                                                                    avg/night
                                                                                    House #3969518
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 10
                                                                                    12
                                                                                    Viewed 145 times in the last 48 hours

                                                                                    Confirmation within 24 hours

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

                                                                                      Excellent! 4.4/5
                                                                                      (9 reviews)
                                                                                      avg/night
                                                                                      Cabin #7006524
                                                                                      • 2 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 5
                                                                                      9
                                                                                      Viewed 74 times in the last 48 hours

                                                                                      Confirmation within 24 hours

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

                                                                                        Exceptional! 5/5
                                                                                        (36 reviews)
                                                                                        avg/night
                                                                                        House #3858756
                                                                                        • 6 BR
                                                                                        • 4 BA
                                                                                        • Sleeps 19
                                                                                        36
                                                                                        Viewed 25 times in the last 48 hours

                                                                                        Confirmation within 24 hours

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

                                                                                          Excellent! 4.7/5
                                                                                          (14 reviews)
                                                                                          avg/night
                                                                                          Townhome #4131667
                                                                                          • 4 BR
                                                                                          • 3 BA
                                                                                          • 1 HF BA
                                                                                          • Sleeps 9
                                                                                          14
                                                                                          Viewed 22 times in the last 48 hours

                                                                                          Confirmation within 24 hours

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

                                                                                            Exceptional! 5/5
                                                                                            (22 reviews)
                                                                                            avg/night
                                                                                            Cottage #3678055
                                                                                            • 2 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 6
                                                                                            22
                                                                                            Viewed 52 times in the last 48 hours

                                                                                            Confirmation within 24 hours

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

                                                                                              Exceptional! 5/5
                                                                                              (14 reviews)
                                                                                              avg/night
                                                                                              House #467417vb
                                                                                              • 4 BR
                                                                                              • 4 BA
                                                                                              • Sleeps 12
                                                                                              14
                                                                                              Viewed 57 times in the last 48 hours

                                                                                              Confirmation within 24 hours

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

                                                                                                Excellent! 4.7/5
                                                                                                (7 reviews)
                                                                                                avg/night
                                                                                                House #3686067
                                                                                                • 4 BR
                                                                                                • 2 BA
                                                                                                • 1 HF BA
                                                                                                • Sleeps 14
                                                                                                7
                                                                                                Viewed 56 times in the last 48 hours

                                                                                                Confirmation within 24 hours

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

                                                                                                  Excellent! 4.7/5
                                                                                                  (23 reviews)
                                                                                                  avg/night
                                                                                                  Lodge #302971vb
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 7
                                                                                                  23
                                                                                                  Viewed 49 times in the last 48 hours

                                                                                                  Confirmation within 24 hours

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

                                                                                                    avg/night
                                                                                                    House #882172vb
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 8
                                                                                                    1
                                                                                                    Viewed 10 times in the last 48 hours

                                                                                                    Confirmation within 24 hours

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

                                                                                                      Exceptional! 5/5
                                                                                                      (15 reviews)
                                                                                                      avg/night
                                                                                                      Cabin #976461
                                                                                                      • 3 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 8
                                                                                                      15
                                                                                                      Viewed 71 times in the last 48 hours

                                                                                                      Confirmation within 24 hours

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

                                                                                                      • 1 - 50 of 300+

                                                                                                      Chestertown Vacation Rentals (300+)