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Chestertown: Houses, Cabins & More

  • 1 - 50
Additional fees apply. Taxes may be added.
    • 3 BR
    • 3 BA
    • Sleeps 8
    8
      • 4 BR
      • 2 BA
      • Sleeps 12
      6
        • 3 BR
        • 2 BA
        • Sleeps 10
        6
          • 6 BR
          • 3 BA
          • Sleeps 20
          13
            • 3 BR
            • 2 BA
            • 1 HF BA
            • Sleeps 8
            12
              • 2 BR
              • 2 BA
              • Sleeps 8
                Very Good! 4.2/5
                (6 reviews)
                avg/night
                • 2 BR
                • 1 BA
                • Sleeps 5
                6
                  Excellent! 4.6/5
                  (14 reviews)
                  avg/night
                  • 2 BR
                  • 2 BA
                  • 1 HF BA
                  • Sleeps 8
                  14
                    Wonderful! 4.9/5
                    (8 reviews)
                    avg/night
                    • 2 BR
                    • 2 BA
                    • Sleeps 4
                    8
                      • 2 BR
                      • 1 BA
                      • Sleeps 6
                      13
                        • 1 BR
                        • 1 BA
                        • Sleeps 6
                        10
                          • 3 BR
                          • 2 BA
                          • Sleeps 8
                          13
                            Excellent! 4.7/5
                            (6 reviews)
                            avg/night
                            • 3 BR
                            • 2 BA
                            • Sleeps 6
                            6
                              Wonderful! 4.9/5
                              (10 reviews)
                              avg/night
                              • 3 BR
                              • 2 BA
                              • Sleeps 8
                              10
                                Very Good! 4.0/5
                                (7 reviews)
                                avg/night
                                • 3 BR
                                • 3 BA
                                • Sleeps 6
                                7
                                  • 2 BR
                                  • 1 BA
                                  • Sleeps 5
                                  4
                                    Excellent! 4.3/5
                                    (17 reviews)
                                    avg/night
                                    • 2 BR
                                    • 1 BA
                                    • Sleeps 6
                                    17
                                      Exceptional! 5.0/5
                                      (5 reviews)
                                      avg/night
                                      • 4 BR
                                      • 2 BA
                                      • Sleeps 10
                                      5
                                        • 2 BR
                                        • 1 BA
                                        • 1 HF BA
                                        • Sleeps 7
                                        8
                                          Exceptional! 5.0/5
                                          (9 reviews)
                                          avg/night
                                          • 4 BR
                                          • 1 BA
                                          • Sleeps 7
                                          9
                                            Exceptional! 5.0/5
                                            (6 reviews)
                                            avg/night
                                            • 3 BR
                                            • 3 BA
                                            • Sleeps 7
                                            6
                                              • 4 BR
                                              • 2 BA
                                              • 1 HF BA
                                              • Sleeps 8
                                                • 4 BR
                                                • 1 BA
                                                • Sleeps 7
                                                1 Review
                                                  • 4 BR
                                                  • 4 BA
                                                  • 1 HF BA
                                                  • Sleeps 16
                                                  1 Review
                                                    • 3 BR
                                                    • 2 BA
                                                    • 1 HF BA
                                                    • Sleeps 6
                                                    2 Reviews
                                                      • 2 BR
                                                      • 1 BA
                                                      • Sleeps 5
                                                      4
                                                        Exceptional! 5.0/5
                                                        (14 reviews)
                                                        avg/night
                                                        • 8 BR
                                                        • 2 BA
                                                        • 1 HF BA
                                                        • Sleeps 16
                                                        14
                                                          • 3 BR
                                                          • 2 BA
                                                          • Sleeps 8
                                                          1 Review
                                                            • 5 BR
                                                            • 3 BA
                                                            • Sleeps 12
                                                            11
                                                              • 2 BR
                                                              • 2 BA
                                                              • Sleeps 4
                                                              3
                                                                • 3 BR
                                                                • 2 BA
                                                                • Sleeps 8
                                                                5
                                                                  • 4 BR
                                                                  • 1 BA
                                                                  • 1 HF BA
                                                                  • Sleeps 12
                                                                  6
                                                                    • 3 BR
                                                                    • 3 BA
                                                                    • 1 HF BA
                                                                    • Sleeps 6
                                                                      • 2 BR
                                                                      • 1 BA
                                                                      • Sleeps 6
                                                                      9
                                                                        Wonderful! 4.9/5
                                                                        (7 reviews)
                                                                        avg/night
                                                                        • 5 BR
                                                                        • 2 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 11
                                                                        7
                                                                          • 5 BR
                                                                          • 3 BA
                                                                          • Sleeps 12
                                                                          15
                                                                            Very Good! 4.0/5
                                                                            (9 reviews)
                                                                            avg/night
                                                                            • 3 BR
                                                                            • 2 BA
                                                                            • Sleeps 10
                                                                            9
                                                                              Exceptional! 5.0/5
                                                                              (5 reviews)
                                                                              avg/night
                                                                              • 5 BR
                                                                              • 2 BA
                                                                              • Sleeps 10
                                                                              5
                                                                                • 3 BR
                                                                                • 1 BA
                                                                                • Sleeps 6
                                                                                2 Reviews
                                                                                  • 6 BR
                                                                                  • 3 BA
                                                                                  • 1 HF BA
                                                                                  • Sleeps 14
                                                                                  8
                                                                                    • 6 BR
                                                                                    • 3 BA
                                                                                    • 1 HF BA
                                                                                    • Sleeps 12
                                                                                    4
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 8
                                                                                      1 Review
                                                                                        Very Good! 4.2/5
                                                                                        (5 reviews)
                                                                                        avg/night
                                                                                        • 4 BR
                                                                                        • 5 BA
                                                                                        • Sleeps 12
                                                                                        5
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 8
                                                                                          2 Reviews
                                                                                            • 6 BR
                                                                                            • 3 BA
                                                                                            • 1 HF BA
                                                                                            • Sleeps 14
                                                                                              • Studio
                                                                                              • 3 BA
                                                                                              • Sleeps 8
                                                                                              1 Review
                                                                                                • 3 BR
                                                                                                • 2 BA
                                                                                                • 1 HF BA
                                                                                                • Sleeps 6
                                                                                                1 Review
                                                                                                  • 3 BR
                                                                                                  • 3 BA
                                                                                                  • 1 HF BA
                                                                                                  • Sleeps 6
                                                                                                    • 5 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 12
                                                                                                    • 1 - 50
                                                                                                     

                                                                                                    Recent Chestertown Reviews

                                                                                                    Great stay

                                                                                                    5 of 5
                                                                                                    We had a great, relaxing weekend here. The home was very clean and spacious for 4 adults and 2 kids. Way better than staying at a hotel. Joe, the owner, provided us with homemade scones when we arrived and they were delicious. Will definitely stay here again!!!
                                                                                                    • Submitted: Sep 28, 2016
                                                                                                    • Stayed: Sep 2016

                                                                                                    Awesome stay!

                                                                                                    5 of 5
                                                                                                    We spent a beautiful Fall weekend in the Adirondacks. The condo was perfect! Homey, cozy , the bed was comfy. Definitely would come back again. Thanks Sally!!!
                                                                                                    • Submitted: Sep 25, 2016
                                                                                                    • Stayed: Sep 2016

                                                                                                    Well built home on Loon lake

                                                                                                    4 of 5
                                                                                                    2x6 construction, well appointed with 2 decks & privacy. We enjoyed our week on Loon lake. HOA beach area with private dock. We enjoyed canoeing & fishing on the lake. Great restaurants & golf in the area. Our week went too fast.
                                                                                                    • Submitted: Sep 20, 2016
                                                                                                    • Stayed: Sep 2016