check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar
Cancel Clear Filters Apply Filters

Property Type

Booking Options

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!
  • 1 - 50 of 174
Additional fees apply. Taxes may be added.
    • 4 BR
    • 2 BA
    • Sleeps 12
    6
      • 3 BR
      • 2 BA
      • Sleeps 10
      6
        • 6 BR
        • 3 BA
        • Sleeps 20
        13
          • 2 BR
          • 2 BA
          • Sleeps 4
          8
            • 3 BR
            • 2 BA
            • Sleeps 8
            13
              • 3 BR
              • 2 BA
              • Sleeps 8
              10
                • 4 BR
                • 2 BA
                • Sleeps 10
                5
                  • 3 BR
                  • 2 BA
                  • 1 HF BA
                  • Sleeps 6
                  2 Reviews
                    • 4 BR
                    • 4 BA
                    • Sleeps 13
                    4
                      • 4 BR
                      • 3 BA
                      • 1 HF BA
                      • Sleeps 12
                      19
                        • 3 BR
                        • 3 BA
                        • Sleeps 8
                        3
                          • 3 BR
                          • 2 BA
                          • Sleeps 10
                            • 3 BR
                            • 2 BA
                            • Sleeps 8
                            1 Review
                              • 5 BR
                              • 3 BA
                              • 1 HF BA
                              • Sleeps 14
                                • 4 BR
                                • 3 BA
                                • Sleeps 14
                                3
                                  • 4 BR
                                  • 2 BA
                                  • Sleeps 12
                                  3
                                    • 5 BR
                                    • 3 BA
                                    • Sleeps 12
                                    11
                                      • 4 BR
                                      • 1 BA
                                      • 1 HF BA
                                      • Sleeps 7
                                        • 3 BR
                                        • 2 BA
                                        • Sleeps 10
                                        41
                                          • 4 BR
                                          • 2 BA
                                          • Sleeps 12
                                          62
                                            • 4 BR
                                            • 1 BA
                                            • Sleeps 7
                                            3
                                              • 3 BR
                                              • 2 BA
                                              • Sleeps 8
                                              5
                                                • 3 BR
                                                • 2 BA
                                                • Sleeps 10
                                                4
                                                  • 4 BR
                                                  • 1 BA
                                                  • 1 HF BA
                                                  • Sleeps 12
                                                  6
                                                    • 5 BR
                                                    • 3 BA
                                                    • Sleeps 12
                                                    15
                                                      • 3 BR
                                                      • 2 BA
                                                      • Sleeps 8
                                                      6
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 10
                                                        9
                                                          • 5 BR
                                                          • 2 BA
                                                          • Sleeps 10
                                                          5
                                                            • 3 BR
                                                            • 1 BA
                                                            • Sleeps 6
                                                            2 Reviews
                                                              • 6 BR
                                                              • 3 BA
                                                              • 1 HF BA
                                                              • Sleeps 12
                                                              4
                                                                • 3 BR
                                                                • 2 BA
                                                                • Sleeps 8
                                                                1 Review
                                                                  • 4 BR
                                                                  • 5 BA
                                                                  • Sleeps 12
                                                                  5
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 7
                                                                    6
                                                                      • 5 BR
                                                                      • 4 BA
                                                                      • Sleeps 11
                                                                      1 Review
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • Sleeps 7
                                                                        3
                                                                          • 6 BR
                                                                          • 3 BA
                                                                          • 1 HF BA
                                                                          • Sleeps 14
                                                                            • 3 BR
                                                                            • 2 BA
                                                                            • Sleeps 10
                                                                            6
                                                                              • 5 BR
                                                                              • 3 BA
                                                                              • Sleeps 12
                                                                              37
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Sleeps 6
                                                                                3
                                                                                  • 5 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 11
                                                                                  4
                                                                                    • 2 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 4
                                                                                      • Studio
                                                                                      • 3 BA
                                                                                      • Sleeps 8
                                                                                      1 Review
                                                                                        • 6 BR
                                                                                        • 4 BA
                                                                                        • Sleeps 12
                                                                                        6
                                                                                          • 3 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 8
                                                                                          6
                                                                                            • 3 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 8
                                                                                            2 Reviews
                                                                                              • 5 BR
                                                                                              • 3 BA
                                                                                              • Sleeps 10
                                                                                              3
                                                                                                • 5 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 10
                                                                                                7
                                                                                                  • 4 BR
                                                                                                  • 1 BA
                                                                                                  • 1 HF BA
                                                                                                  • Sleeps 10
                                                                                                  2 Reviews
                                                                                                  • 1 - 50 of 174
                                                                                                   

                                                                                                  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

                                                                                                  very nice home.

                                                                                                  5 of 5
                                                                                                  we stayed here sept 16 till the 21st of 2016. a really nice house thats just a short walk down to the lake. bring linens and towels tho because they are not provided. everything else that you need is there.
                                                                                                  • Submitted: Sep 23, 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