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  • Showing 1-50 of 300+
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    • 1 BR
    • 1 BA
    • Sleeps 6
    Condo #3896538
    11
      • 2 BR
      • 1 BA
      • Sleeps 6
      Condo #716031vb
      14
        • 3 BR
        • 3 BA
        • Sleeps 8
        Cottage #175549
        8
          Very Good! 4.2/5
          (6 reviews)
          avg/night
          • 2 BR
          • 1 BA
          • Sleeps 5
          Condo #3804012
          6
            • 4 BR
            • 2 BA
            • Sleeps 12
            House #4240841
            10
              • 3 BR
              • 2 BA
              • Sleeps 10
              House #3924952
              6
                Wonderful! 4.9/5
                (10 reviews)
                avg/night
                • 2 BR
                • 2 BA
                • Sleeps 4
                House #4044539
                10
                  Exceptional! 5.0/5
                  (6 reviews)
                  avg/night
                  • 3 BR
                  • 3 BA
                  • Sleeps 7
                  Townhome #689905vb
                  6
                    Very Good! 4.1/5
                    (8 reviews)
                    avg/night
                    • 3 BR
                    • 3 BA
                    • Sleeps 6
                    Condo #4014526
                    8
                      • 2 BR
                      • 2 BA
                      • Sleeps 8
                      Cabin #4222462
                        Excellent! 4.3/5
                        (17 reviews)
                        avg/night
                        • 2 BR
                        • 1 BA
                        • Sleeps 6
                        Cabin #3014265
                        17
                          Exceptional! 5.0/5
                          (5 reviews)
                          avg/night
                          • 4 BR
                          • 2 BA
                          • Sleeps 10
                          House #876933vb
                          5
                            • 2 BR
                            • 1 BA
                            • 1 HF BA
                            • Sleeps 7
                            Cottage #3828287
                            8
                              • 3 BR
                              • 2 BA
                              • Sleeps 8
                              House #4073769
                              15
                                Excellent! 4.6/5
                                (14 reviews)
                                avg/night
                                • 2 BR
                                • 2 BA
                                • 1 HF BA
                                • Sleeps 8
                                Cabin #641786vb
                                14
                                  Wonderful! 4.8/5
                                  (13 reviews)
                                  avg/night
                                  • 3 BR
                                  • 1 BA
                                  • Sleeps 8
                                  House #7080936
                                  13
                                    Good! 3.8/5
                                    (5 reviews)
                                    avg/night
                                    • 2 BR
                                    • 1 BA
                                    • Sleeps 5
                                    Cabin #3016070
                                    5
                                      • 6 BR
                                      • 3 BA
                                      • Sleeps 20
                                      House #258920
                                      13
                                        Exceptional! 5.0/5
                                        (9 reviews)
                                        avg/night
                                        • 4 BR
                                        • 1 BA
                                        • Sleeps 7
                                        Cottage #3496194
                                        9
                                          • 4 BR
                                          • 2 BA
                                          • 1 HF BA
                                          • Sleeps 8
                                          Chalet #593993vb
                                            • 3 BR
                                            • 2 BA
                                            • 1 HF BA
                                            • Sleeps 8
                                            Townhome #978720
                                            13
                                              • 4 BR
                                              • 1 BA
                                              • Sleeps 7
                                              Cottage #3667204
                                              1
                                                • 6 BR
                                                • 2 BA
                                                • Sleeps 11
                                                Lodge #3727616
                                                1
                                                  • 3 BR
                                                  • 2 BA
                                                  • Sleeps 9
                                                  House #4313390
                                                    • 2 BR
                                                    • 1 BA
                                                    • Sleeps 6
                                                    Apartment #948565vb
                                                      • 5 BR
                                                      • 2 BA
                                                      • Sleeps 8
                                                      House #239560
                                                        • 4 BR
                                                        • 2 BA
                                                        • Sleeps 13
                                                        House #948569vb
                                                          • 4 BR
                                                          • 4 BA
                                                          • 1 HF BA
                                                          • Sleeps 16
                                                          Apartment #3726412
                                                          1
                                                            • 6 BR
                                                            • 3 BA
                                                            • Sleeps 12
                                                            House #557834vb
                                                            1
                                                              Wonderful! 4.9/5
                                                              (64 reviews)
                                                              avg/night
                                                              • 5 BR
                                                              • 3 BA
                                                              • 1 HF BA
                                                              • Sleeps 16
                                                              House #179508
                                                              64
                                                                • 7 BR
                                                                • 6 BA
                                                                • 1 HF BA
                                                                • Sleeps 18
                                                                House #3001286
                                                                91
                                                                  Wonderful! 4.9/5
                                                                  (32 reviews)
                                                                  avg/night
                                                                  • 5 BR
                                                                  • 3 BA
                                                                  • 2 HF BA
                                                                  • Sleeps 15
                                                                  House #3876403
                                                                  32
                                                                    • 4 BR
                                                                    • 3 BA
                                                                    • 1 HF BA
                                                                    • Sleeps 9
                                                                    Townhome #4131667
                                                                    14
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Sleeps 10
                                                                      House #423420vb
                                                                      46
                                                                        Exceptional! 5.0/5
                                                                        (25 reviews)
                                                                        avg/night
                                                                        • 5 BR
                                                                        • 4 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 12
                                                                        House #3540173
                                                                        25
                                                                          Wonderful! 4.9/5
                                                                          (7 reviews)
                                                                          avg/night
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • Sleeps 7
                                                                          House #863326vb
                                                                          7
                                                                            • 6 BR
                                                                            • 4 BA
                                                                            • Sleeps 19
                                                                            House #3858756
                                                                            36
                                                                              Very Good! 4.2/5
                                                                              (12 reviews)
                                                                              avg/night
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 10
                                                                              House #3969518
                                                                              12
                                                                                • 4 BR
                                                                                • 2 BA
                                                                                • Sleeps 14
                                                                                House #288198vb
                                                                                40
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 8
                                                                                  House #720321vb
                                                                                  6
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 7
                                                                                    Lodge #302971vb
                                                                                    23
                                                                                      Exceptional! 5.0/5
                                                                                      (22 reviews)
                                                                                      avg/night
                                                                                      • 2 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 6
                                                                                      Cottage #3678055
                                                                                      22
                                                                                        Excellent! 4.5/5
                                                                                        (8 reviews)
                                                                                        avg/night
                                                                                        • 2 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 5
                                                                                        Cabin #7006524
                                                                                        8
                                                                                          • 4 BR
                                                                                          • 2 BA
                                                                                          • 1 HF BA
                                                                                          • Sleeps 14
                                                                                          House #3686067
                                                                                          6
                                                                                            Very Good! 4.2/5
                                                                                            (9 reviews)
                                                                                            avg/night
                                                                                            • 2 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 5
                                                                                            Cottage #3953323
                                                                                            9
                                                                                              • 5 BR
                                                                                              • 3 BA
                                                                                              • Sleeps 12
                                                                                              House #480124vb
                                                                                              40
                                                                                                • 2 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 6
                                                                                                Cabin #802195vb
                                                                                                11
                                                                                                  Wonderful! 4.9/5
                                                                                                  (42 reviews)
                                                                                                  avg/night
                                                                                                  • 6 BR
                                                                                                  • 4 BA
                                                                                                  • 1 HF BA
                                                                                                  • Sleeps 16
                                                                                                  House #294583
                                                                                                  42
                                                                                                    Exceptional! 5.0/5
                                                                                                    (15 reviews)
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 8
                                                                                                    Cabin #976461
                                                                                                    15
                                                                                                      Exceptional! 5.0/5
                                                                                                      (14 reviews)
                                                                                                      avg/night
                                                                                                      • 4 BR
                                                                                                      • 4 BA
                                                                                                      • Sleeps 12
                                                                                                      House #467417vb
                                                                                                      14
                                                                                                      • 1 - 50 of 300+

                                                                                                      Chestertown: Houses, Cabins & More (300+)

                                                                                                       

                                                                                                      Recent Chestertown Reviews

                                                                                                      Great experience

                                                                                                      5 of 5
                                                                                                      Our family of eleven booked a trip to the Adirondacks in lieu of buying Christmas present for eachother this year. This house was absolutely beautiful and accommodated all of us perfectly.
                                                                                                      • Submitted: Jan 17, 2017
                                                                                                      • Stayed: Jan 2017

                                                                                                      Beautiful house with a helpful, kind owner!

                                                                                                      5 of 5
                                                                                                      We had a great winter weekend in Lake George! The house was perfect with plenty of room for our large group. The hottub was amazing after a day skiing, and we look forward to coming back one summer to try out the pool! Charlie was very helpful and answered all of our questions promptly during the weekend. I definitely recommend.
                                                                                                      • Submitted: Jan 16, 2017
                                                                                                      • Stayed: Jan 2017

                                                                                                      Wonderul weekend away

                                                                                                      5 of 5
                                                                                                      Joe is a great host and his home is lovely and very well equipped The village location is quite nice and a convenient base for skiing ay Gore
                                                                                                      • Submitted: Jan 15, 2017
                                                                                                      • Stayed: Jan 2017