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  • Showing 1-50 of 300+
Additional fees apply. Taxes may be added.
    Excellent! 4.4/5
    (11 reviews)
    $97
    avg/night
    • 1 BR
    • 1 BA
    • Sleeps 6
    Condo #3896538
    11
    Viewed 16 times in the last 48 hours
      • 2 BR
      • 1 BA
      • Sleeps 6
      Condo #716031vb
      14
        Wonderful! 4.9/5
        (8 reviews)
        avg/night
        • 3 BR
        • 3 BA
        • Sleeps 8
        Cottage #175549
        8
        Viewed 9 times in the last 48 hours
          Very Good! 4.0/5
          (7 reviews)
          avg/night
          • 3 BR
          • 3 BA
          • Sleeps 6
          Condo #4014526
          7
          Viewed 21 times in the last 48 hours
            Wonderful! 4.8/5
            (9 reviews)
            avg/night
            • 4 BR
            • 2 BA
            • Sleeps 12
            House #4240841
            9
            Viewed 9 times in the last 48 hours
              Exceptional! 5.0/5
              (6 reviews)
              avg/night
              • 3 BR
              • 2 BA
              • Sleeps 10
              House #3924952
              6
              Viewed 9 times in the last 48 hours
                • 3 BR
                • 2 BA
                • Sleeps 8
                House #4073769
                13
                  Wonderful! 4.8/5
                  (12 reviews)
                  avg/night
                  • 3 BR
                  • 2 BA
                  • Sleeps 8
                  House #7080936
                  12
                  Viewed 8 times in the last 48 hours
                    Excellent! 4.3/5
                    (17 reviews)
                    avg/night
                    • 2 BR
                    • 1 BA
                    • Sleeps 6
                    Cabin #3014265
                    17
                    Viewed 49 times in the last 48 hours
                      • 2 BR
                      • 2 BA
                      • Sleeps 8
                      Cabin #4222462
                        Very Good! 4.2/5
                        (6 reviews)
                        avg/night
                        • 2 BR
                        • 1 BA
                        • Sleeps 5
                        Condo #3804012
                        6
                        Viewed 8 times in the last 48 hours
                          Wonderful! 4.9/5
                          (8 reviews)
                          avg/night
                          • 2 BR
                          • 2 BA
                          • Sleeps 4
                          House #4044539
                          8
                            Good! 3.8/5
                            (5 reviews)
                            avg/night
                            • 2 BR
                            • 1 BA
                            • Sleeps 5
                            Cabin #3016070
                            5
                            Viewed 5 times in the last 48 hours
                              Exceptional! 5.0/5
                              (9 reviews)
                              avg/night
                              • 4 BR
                              • 1 BA
                              • Sleeps 7
                              Cottage #3496194
                              9
                              Viewed 8 times in the last 48 hours
                                Exceptional! 5.0/5
                                (5 reviews)
                                • 4 BR
                                • 2 BA
                                • Sleeps 10
                                House #876933vb
                                5
                                Viewed 9 times in the last 48 hours
                                  Excellent! 4.6/5
                                  (14 reviews)
                                  avg/night
                                  • 2 BR
                                  • 2 BA
                                  • 1 HF BA
                                  • Sleeps 8
                                  Cabin #641786vb
                                  14
                                  Viewed 17 times in the last 48 hours
                                    Excellent! 4.7/5
                                    (7 reviews)
                                    avg/night
                                    • 3 BR
                                    • 2 BA
                                    • Sleeps 6
                                    Cabin #4231925
                                    7
                                    Viewed 41 times in the last 48 hours
                                      Excellent! 4.5/5
                                      (8 reviews)
                                      avg/night
                                      • 2 BR
                                      • 1 BA
                                      • 1 HF BA
                                      • Sleeps 7
                                      Cottage #3828287
                                      8
                                      Viewed 24 times in the last 48 hours
                                        • 4 BR
                                        • 2 BA
                                        • 1 HF BA
                                        • Sleeps 8
                                        Chalet #593993vb
                                          Exceptional! 5.0/5
                                          (6 reviews)
                                          avg/night
                                          • 3 BR
                                          • 3 BA
                                          • Sleeps 7
                                          Townhome #689905vb
                                          6
                                            Excellent! 4.3/5
                                            (13 reviews)
                                            avg/night
                                            • 6 BR
                                            • 3 BA
                                            • Sleeps 20
                                            House #258920
                                            13
                                            Viewed 51 times in the last 48 hours
                                              avg/night
                                              • 6 BR
                                              • 2 BA
                                              • Sleeps 11
                                              Lodge #3727616
                                              1 Review
                                              Viewed 8 times in the last 48 hours
                                                Wonderful! 4.8/5
                                                (12 reviews)
                                                avg/night
                                                • 3 BR
                                                • 2 BA
                                                • 1 HF BA
                                                • Sleeps 8
                                                Townhome #978720
                                                12
                                                Viewed 67 times in the last 48 hours
                                                  avg/night
                                                  • 4 BR
                                                  • 1 BA
                                                  • Sleeps 7
                                                  Cottage #3667204
                                                  1 Review
                                                  Viewed 8 times in the last 48 hours
                                                    • 3 BR
                                                    • 2 BA
                                                    • Sleeps 9
                                                    House #4313390
                                                    Viewed 31 times in the last 48 hours
                                                      avg/night
                                                      • 4 BR
                                                      • 4 BA
                                                      • 1 HF BA
                                                      • Sleeps 16
                                                      Apartment #3726412
                                                      1 Review
                                                      Viewed 8 times in the last 48 hours
                                                        • 3 BR
                                                        • 2 BA
                                                        • 1 HF BA
                                                        • Sleeps 6
                                                        House #863696vb
                                                        2 Reviews
                                                          Wonderful! 4.9/5
                                                          (44 reviews)
                                                          avg/night
                                                          • 3 BR
                                                          • 2 BA
                                                          • Sleeps 10
                                                          House #423420vb
                                                          44
                                                          Viewed 54 times in the last 48 hours
                                                            Exceptional! 5.0/5
                                                            (20 reviews)
                                                            avg/night
                                                            • 3 BR
                                                            • 1 BA
                                                            • 1 HF BA
                                                            • Sleeps 8
                                                            Cottage #601005vb
                                                            20
                                                            Viewed 22 times in the last 48 hours
                                                              Exceptional! 5.0/5
                                                              (35 reviews)
                                                              avg/night
                                                              • 6 BR
                                                              • 4 BA
                                                              • Sleeps 19
                                                              House #3858756
                                                              35
                                                              Viewed 15 times in the last 48 hours
                                                                avg/night
                                                                • 4 BR
                                                                • 2 BA
                                                                • 1 HF BA
                                                                • Sleeps 10
                                                                Chateau / Country House #967178vb
                                                                Viewed 21 times in the last 48 hours
                                                                  avg/night
                                                                  • 3 BR
                                                                  • 2 BA
                                                                  • Sleeps 12
                                                                  Chalet #7099746
                                                                  1 Review
                                                                  Viewed 9 times in the last 48 hours
                                                                    • 2 BR
                                                                    • 1 BA
                                                                    • Sleeps 6
                                                                    Cabin #3768068
                                                                    4
                                                                    Viewed 6 times in the last 48 hours
                                                                      Wonderful! 4.9/5
                                                                      (7 reviews)
                                                                      avg/night
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Sleeps 7
                                                                      House #863326vb
                                                                      7
                                                                      Viewed 28 times in the last 48 hours
                                                                        Exceptional! 5.0/5
                                                                        (8 reviews)
                                                                        avg/night
                                                                        • 4 BR
                                                                        • 3 BA
                                                                        • Sleeps 8
                                                                        House #151600
                                                                        8
                                                                        Viewed 7 times in the last 48 hours
                                                                          Wonderful! 4.9/5
                                                                          (62 reviews)
                                                                          avg/night
                                                                          • 4 BR
                                                                          • 2 BA
                                                                          • Sleeps 12
                                                                          House #76007vb
                                                                          62
                                                                          Viewed 13 times in the last 48 hours
                                                                            • 4 BR
                                                                            • 3 BA
                                                                            • Sleeps 12
                                                                            House #962469vb
                                                                            1 Review
                                                                            Viewed 9 times in the last 48 hours
                                                                              Exceptional! 5.0/5
                                                                              (7 reviews)
                                                                              avg/night
                                                                              • 2 BR
                                                                              • 1 BA
                                                                              • Sleeps 5
                                                                              Cabin #3646886
                                                                              7
                                                                              Viewed 13 times in the last 48 hours
                                                                                Exceptional! 5.0/5
                                                                                (6 reviews)
                                                                                avg/night
                                                                                • 4 BR
                                                                                • 2 BA
                                                                                • 1 HF BA
                                                                                • Sleeps 14
                                                                                House #3686067
                                                                                6
                                                                                Viewed 35 times in the last 48 hours
                                                                                  Exceptional! 5.0/5
                                                                                  (6 reviews)
                                                                                  avg/night
                                                                                  • 6 BR
                                                                                  • 4 BA
                                                                                  • Sleeps 12
                                                                                  House #748866vb
                                                                                  6
                                                                                  Viewed 10 times in the last 48 hours
                                                                                    avg/night
                                                                                    • 2 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 4
                                                                                    House #4084910
                                                                                    Viewed 16 times in the last 48 hours
                                                                                      Wonderful! 4.8/5
                                                                                      (12 reviews)
                                                                                      avg/night
                                                                                      • 5 BR
                                                                                      • 3 BA
                                                                                      • Sleeps 12
                                                                                      House #189443
                                                                                      12
                                                                                      Viewed 34 times in the last 48 hours
                                                                                        Wonderful! 4.9/5
                                                                                        (39 reviews)
                                                                                        avg/night
                                                                                        • 5 BR
                                                                                        • 3 BA
                                                                                        • Sleeps 12
                                                                                        House #480124vb
                                                                                        39
                                                                                        Viewed 57 times in the last 48 hours
                                                                                          avg/night
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • 1 HF BA
                                                                                          • Sleeps 8
                                                                                          House #834979vb
                                                                                          2 Reviews
                                                                                          Viewed 19 times in the last 48 hours
                                                                                            avg/night
                                                                                            • 4 BR
                                                                                            • 3 BA
                                                                                            • 1 HF BA
                                                                                            • Sleeps 8
                                                                                            Cabin #457327vb
                                                                                            2 Reviews
                                                                                            Viewed 6 times in the last 48 hours
                                                                                              Wonderful! 4.9/5
                                                                                              (28 reviews)
                                                                                              avg/night
                                                                                              • 5 BR
                                                                                              • 3 BA
                                                                                              • 2 HF BA
                                                                                              • Sleeps 15
                                                                                              House #3876403
                                                                                              28
                                                                                              Viewed 16 times in the last 48 hours
                                                                                                • 2 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 6
                                                                                                Cottage #4120291
                                                                                                Viewed 6 times in the last 48 hours
                                                                                                  Excellent! 4.4/5
                                                                                                  (5 reviews)
                                                                                                  avg/night
                                                                                                  • 2 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 8
                                                                                                  Apartment #3685822
                                                                                                  5
                                                                                                  Viewed 6 times in the last 48 hours
                                                                                                    Excellent! 4.7/5
                                                                                                    (6 reviews)
                                                                                                    avg/night
                                                                                                    • 4 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 10
                                                                                                    House #627154vb
                                                                                                    6
                                                                                                    Viewed 37 times in the last 48 hours
                                                                                                      Wonderful! 4.9/5
                                                                                                      (35 reviews)
                                                                                                      avg/night
                                                                                                      • 3 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 9
                                                                                                      Cabin #253917
                                                                                                      35
                                                                                                      Viewed 17 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Chestertown: Houses, Cottages & More (300+)

                                                                                                       

                                                                                                      Recent Chestertown Reviews

                                                                                                      Great spot for a group / family gathering

                                                                                                      5 of 5
                                                                                                      Our family of 10 had a great time here, well appointed and a great place to get together. The owners were very responsive and helpful.
                                                                                                      • Submitted: Nov 27, 2016
                                                                                                      • Stayed: Nov 2016

                                                                                                      Beautiful Late Fall Weekend at Lake George

                                                                                                      5 of 5
                                                                                                      We had 8 adults for a weekend stay at the Mountain House for a visit to The Sagamore Resort for wedding planning. Our group enjoyed the large kitchen, dining room and comfortable living room. The new 50 inch HDTV was super for viewing football games. The views of Lake George are postcard perfect off the main floor deck. We definitely will be back in 2017.
                                                                                                      • Submitted: Nov 17, 2016
                                                                                                      • Stayed: Nov 2016

                                                                                                      Fantastic, clean

                                                                                                      4 of 5
                                                                                                      home was clean and extremely cozy!
                                                                                                      • Submitted: Oct 17, 2016
                                                                                                      • Stayed: Oct 2016