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    Excellent! 4.6/5
    (16 reviews)
    avg/night
    • 1 BR
    • 1 BA
    • Sleeps 6
    Condo #3896538
    16
    Viewed 52 times in the last 48 hours
      Wonderful! 4.8/5
      (17 reviews)
      avg/night
      • 2 BR
      • 1 BA
      • Sleeps 6
      Condo #716031vb
      17
      Viewed 55 times in the last 48 hours
        Excellent! 4.3/5
        (18 reviews)
        avg/night
        • 2 BR
        • 1 BA
        • Sleeps 6
        Cabin #3014265
        18
        Viewed 71 times in the last 48 hours
          Excellent! 4.3/5
          (8 reviews)
          avg/night
          • 2 BR
          • 1 BA
          • Sleeps 5
          Condo #3804012
          8
          Viewed 39 times in the last 48 hours
            Very Good! 4/5
            (11 reviews)
            avg/night
            • 3 BR
            • 3 BA
            • Sleeps 6
            Condo #4014526
            11
            Viewed 69 times in the last 48 hours
              Wonderful! 4.9/5
              (11 reviews)
              avg/night
              • 3 BR
              • 3 BA
              • Sleeps 8
              Cottage #175549
              11
              Viewed 43 times in the last 48 hours
                Wonderful! 4.9/5
                (19 reviews)
                avg/night
                • 2 BR
                • 2 BA
                • Sleeps 4
                House #4044539
                19
                Viewed 35 times in the last 48 hours
                  Exceptional! 5/5
                  (10 reviews)
                  avg/night
                  • 3 BR
                  • 2 BA
                  • Sleeps 10
                  House #3924952
                  10
                  Viewed 42 times in the last 48 hours
                    Very Good! 4/5
                    (7 reviews)
                    avg/night
                    • 2 BR
                    • 1 BA
                    • Sleeps 5
                    Cabin #3016070
                    7
                    Viewed 58 times in the last 48 hours
                      Wonderful! 4.9/5
                      (14 reviews)
                      avg/night
                      • 4 BR
                      • 2 BA
                      • Sleeps 12
                      House #4240841
                      14
                      Viewed 49 times in the last 48 hours
                        Exceptional! 5/5
                        (5 reviews)
                        avg/night
                        • 3 BR
                        • 2 BA
                        • Sleeps 9
                        House #4313390
                        5
                        Viewed 10 times in the last 48 hours
                          Exceptional! 5/5
                          (8 reviews)
                          avg/night
                          • 3 BR
                          • 3 BA
                          • Sleeps 7
                          Townhome #689905vb
                          8
                          Viewed 5 times in the last 48 hours
                            Wonderful! 4.9/5
                            (21 reviews)
                            avg/night
                            • 3 BR
                            • 2 BA
                            • Sleeps 8
                            House #4073769
                            21
                            Viewed 15 times in the last 48 hours
                              Wonderful! 4.8/5
                              (24 reviews)
                              avg/night
                              • 3 BR
                              • 1 BA
                              • Sleeps 8
                              House #7080936
                              24
                              Viewed 37 times in the last 48 hours
                                Exceptional! 5/5
                                (10 reviews)
                                avg/night
                                • 4 BR
                                • 1 BA
                                • Sleeps 7
                                Cottage #3496194
                                10
                                Viewed 8 times in the last 48 hours
                                  Very Good! 4.2/5
                                  (14 reviews)
                                  avg/night
                                  • 6 BR
                                  • 3 BA
                                  • Sleeps 26
                                  House #258920
                                  14
                                  Viewed 90 times in the last 48 hours
                                    Excellent! 4.6/5
                                    (10 reviews)
                                    avg/night
                                    • 2 BR
                                    • 1 BA
                                    • 1 HF BA
                                    • Sleeps 7
                                    Cottage #3828287
                                    10
                                    Viewed 42 times in the last 48 hours
                                      avg/night
                                      • 4 BR
                                      • 2 BA
                                      • Sleeps 8
                                      Cottage #1020543vb
                                      2
                                      Viewed 29 times in the last 48 hours
                                        • 6 BR
                                        • 3 BA
                                        • Sleeps 12
                                        House #557834vb
                                        1
                                        Viewed 22 times in the last 48 hours
                                          • 2 BR
                                          • 1 BA
                                          • 1 HF BA
                                          • Sleeps 7
                                          Condo #1036429vb
                                          1
                                          Viewed 20 times in the last 48 hours
                                            avg/night
                                            • 4 BR
                                            • 2 BA
                                            • 1 HF BA
                                            • Sleeps 8
                                            Chalet #593993vb
                                            Viewed 13 times in the last 48 hours
                                              Excellent! 4.6/5
                                              (17 reviews)
                                              avg/night
                                              • 2 BR
                                              • 2 BA
                                              • 1 HF BA
                                              • Sleeps 8
                                              Cabin #641786vb
                                              17
                                              Viewed 15 times in the last 48 hours
                                                avg/night
                                                • 7 BR
                                                • 4 BA
                                                • Sleeps 18
                                                House #1034527vb
                                                Viewed 141 times in the last 48 hours
                                                  avg/night
                                                  • 3 BR
                                                  • 2 BA
                                                  • 1 HF BA
                                                  • Sleeps 8
                                                  Townhome #1115287vb
                                                  Viewed 106 times in the last 48 hours
                                                    avg/night
                                                    • 2 BR
                                                    • 2 BA
                                                    • Sleeps 6
                                                    Cabin #4087680
                                                    Viewed 98 times in the last 48 hours
                                                      • 6 BR
                                                      • 2 BA
                                                      • Sleeps 11
                                                      Lodge #3727616
                                                      1
                                                      Viewed 34 times in the last 48 hours
                                                        avg/night
                                                        • 4 BR
                                                        • 2 BA
                                                        • Sleeps 13
                                                        House #948569vb
                                                        2
                                                        Viewed 84 times in the last 48 hours
                                                          avg/night
                                                          • 2 BR
                                                          • 1 BA
                                                          • Sleeps 8
                                                          Cottage #4473478
                                                          2
                                                          Viewed 31 times in the last 48 hours
                                                            avg/night
                                                            • 3 BR
                                                            • 2 BA
                                                            • Sleeps 9
                                                            House #4479049
                                                            1
                                                            Viewed 10 times in the last 48 hours
                                                              Exceptional! 5/5
                                                              (31 reviews)
                                                              avg/night
                                                              • 3 BR
                                                              • 2 BA
                                                              • Sleeps 9
                                                              Chalet #3348vb
                                                              31
                                                              Viewed 36 times in the last 48 hours
                                                                avg/night
                                                                • 3 BR
                                                                • 2 BA
                                                                • 1 HF BA
                                                                • Sleeps 6
                                                                Townhome #1115909vb
                                                                Viewed 51 times in the last 48 hours
                                                                  avg/night
                                                                  • 2 BR
                                                                  • 1 BA
                                                                  • Sleeps 6
                                                                  Apartment #948565vb
                                                                  4
                                                                  Viewed 16 times in the last 48 hours
                                                                    avg/night
                                                                    • 1 BR
                                                                    • 1 BA
                                                                    • Sleeps 2
                                                                    Cabin #1021229vb
                                                                    Viewed 13 times in the last 48 hours
                                                                      Exceptional! 5/5
                                                                      (12 reviews)
                                                                      avg/night
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • 1 HF BA
                                                                      • Sleeps 8
                                                                      House #140995
                                                                      12
                                                                      Viewed 33 times in the last 48 hours
                                                                        • 5 BR
                                                                        • 2 BA
                                                                        • Sleeps 8
                                                                        House #239560
                                                                        Viewed 7 times in the last 48 hours
                                                                          Wonderful! 4.9/5
                                                                          (14 reviews)
                                                                          avg/night
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • 1 HF BA
                                                                          • Sleeps 8
                                                                          Townhome #978720
                                                                          14
                                                                          Viewed 23 times in the last 48 hours
                                                                            avg/night
                                                                            • 4 BR
                                                                            • 1 BA
                                                                            • Sleeps 7
                                                                            Cottage #3667204
                                                                            1
                                                                            Viewed 17 times in the last 48 hours
                                                                              • 4 BR
                                                                              • 4 BA
                                                                              • 1 HF BA
                                                                              • Sleeps 16
                                                                              Apartment #3726412
                                                                              1
                                                                                Wonderful! 4.9/5
                                                                                (79 reviews)
                                                                                avg/night
                                                                                • 5 BR
                                                                                • 3 BA
                                                                                • 1 HF BA
                                                                                • Sleeps 18
                                                                                House #179508
                                                                                79
                                                                                Viewed 316 times in the last 48 hours
                                                                                  Exceptional! 5/5
                                                                                  (107 reviews)
                                                                                  avg/night
                                                                                  • 7 BR
                                                                                  • 6 BA
                                                                                  • 1 HF BA
                                                                                  • Sleeps 19
                                                                                  House #3001286
                                                                                  107
                                                                                  Viewed 216 times in the last 48 hours
                                                                                    Wonderful! 4.9/5
                                                                                    (41 reviews)
                                                                                    avg/night
                                                                                    • 6 BR
                                                                                    • 3 BA
                                                                                    • 2 HF BA
                                                                                    • Sleeps 15
                                                                                    House #3876403
                                                                                    41
                                                                                    Viewed 76 times in the last 48 hours
                                                                                      Wonderful! 4.8/5
                                                                                      (15 reviews)
                                                                                      avg/night
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 7
                                                                                      House #863326vb
                                                                                      15
                                                                                      Viewed 152 times in the last 48 hours
                                                                                        Excellent! 4.4/5
                                                                                        (14 reviews)
                                                                                        avg/night
                                                                                        • 2 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 4
                                                                                        Cabin #7006524
                                                                                        14
                                                                                        Viewed 48 times in the last 48 hours
                                                                                          Wonderful! 4.9/5
                                                                                          (17 reviews)
                                                                                          avg/night
                                                                                          • 1 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 2
                                                                                          Cabin #4066619
                                                                                          17
                                                                                          Viewed 39 times in the last 48 hours
                                                                                            Wonderful! 4.9/5
                                                                                            (13 reviews)
                                                                                            avg/night
                                                                                            • 2 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 6
                                                                                            Cabin #802195vb
                                                                                            13
                                                                                            Viewed 174 times in the last 48 hours
                                                                                              Exceptional! 5/5
                                                                                              (28 reviews)
                                                                                              avg/night
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 6
                                                                                              Cottage #3678055
                                                                                              28
                                                                                              Viewed 29 times in the last 48 hours
                                                                                                Wonderful! 4.8/5
                                                                                                (55 reviews)
                                                                                                avg/night
                                                                                                • 3 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 10
                                                                                                House #423420vb
                                                                                                55
                                                                                                Viewed 119 times in the last 48 hours
                                                                                                  Exceptional! 5/5
                                                                                                  (44 reviews)
                                                                                                  View details for price
                                                                                                  • 6 BR
                                                                                                  • 4 BA
                                                                                                  • Sleeps 19
                                                                                                  House #3858756
                                                                                                  44
                                                                                                  Viewed 39 times in the last 48 hours
                                                                                                    Wonderful! 4.9/5
                                                                                                    (15 reviews)
                                                                                                    avg/night
                                                                                                    • 4 BR
                                                                                                    • 3 BA
                                                                                                    • 1 HF BA
                                                                                                    • Sleeps 11
                                                                                                    Townhome #145704
                                                                                                    15
                                                                                                    Viewed 98 times in the last 48 hours
                                                                                                      Wonderful! 4.8/5
                                                                                                      (9 reviews)
                                                                                                      avg/night
                                                                                                      • 2 BR
                                                                                                      • 1 BA
                                                                                                      • 1 HF BA
                                                                                                      • Sleeps 8
                                                                                                      House #834979vb
                                                                                                      9
                                                                                                      Viewed 92 times in the last 48 hours

                                                                                                      Vacation Rentals in Chestertown, New York (300+)