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Chestertown: Houses, Estates & More (56)

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    • 3 BR
    • 2 BA
    • Sleeps 6
    2 Reviews
      • 3 BR
      • 2 BA
      • Sleeps 6
      8
        • 2 BR
        • 2 BA
        • Sleeps 5
        1 Review
          NEW!
          • 3 BR
          • 1 BA
          • 1 HF BA
          • Sleeps 6
            • 2 BR
            • 2 BA
            • 1 HF BA
            • Sleeps 6
            1 Review
              • 5 BR
              • 4 BA
              • 1 HF BA
              • Sleeps 10
              3
                • 2 BR
                • 1 BA
                • 1 HF BA
                • Sleeps 6
                22
                  • 3 BR
                  • 1 BA
                  • 1 HF BA
                  • Sleeps 7
                  28
                    • 3 BR
                    • 1 BA
                    • Sleeps 6
                    22
                      • 4 BR
                      • 4 BA
                      • 1 HF BA
                      • Sleeps 10
                      18
                        • 2 BR
                        • 1 BA
                        • 1 HF BA
                        • Sleeps 4
                        8
                          • 5 BR
                          • 3 BA
                          • Sleeps 8
                          5
                            • 4 BR
                            • 2 BA
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                            • Sleeps 11
                              • 4 BR
                              • 2 BA
                              • Sleeps 12
                              17
                                • 3 BR
                                • 2 BA
                                • 1 HF BA
                                • Sleeps 8
                                3
                                  • 3 BR
                                  • 3 BA
                                  • Sleeps 8
                                  36
                                    • 2 BR
                                    • 1 BA
                                    • Sleeps 5
                                    1 Review
                                      • 1 BR
                                      • 1 BA
                                      • Sleeps 5
                                      26
                                        • 3 BR
                                        • 2 BA
                                        • Sleeps 9
                                        7
                                          NEW!
                                          • 1 BR
                                          • 1 BA
                                          • 1 HF BA
                                          • Sleeps 4
                                          3
                                            • 3 BR
                                            • 2 BA
                                            • Sleeps 9
                                            7
                                              • 4 BR
                                              • 2 BA
                                              • Sleeps 10
                                              7
                                                • 2 BR
                                                • 1 BA
                                                • Sleeps 4
                                                3
                                                  • 4 BR
                                                  • 2 BA
                                                  • Sleeps 8
                                                  12
                                                    • 3 BR
                                                    • 2 BA
                                                    • 1 HF BA
                                                    • Sleeps 8
                                                    2 Reviews
                                                      • 4 BR
                                                      • 2 BA
                                                      • Sleeps 10
                                                      11
                                                        • 6 BR
                                                        • 2 BA
                                                        • Sleeps 11
                                                        12
                                                          • 3 BR
                                                          • 2 BA
                                                          • 1 HF BA
                                                          • Sleeps 6
                                                          1 Review
                                                            • 3 BR
                                                            • 2 BA
                                                            • 1 HF BA
                                                            • Sleeps 8
                                                            15
                                                              NEW!
                                                              • 3 BR
                                                              • 1 BA
                                                              • Sleeps 8
                                                                NEW!
                                                                • 3 BR
                                                                • 1 BA
                                                                • Sleeps 6
                                                                  • 2 BR
                                                                  • 1 BA
                                                                  • Sleeps 6
                                                                  17
                                                                    • 3 BR
                                                                    • 1 BA
                                                                    • 1 HF BA
                                                                    • Sleeps 8
                                                                    9
                                                                      • 2 BR
                                                                      • 1 BA
                                                                      • Sleeps 6
                                                                      1 Review
                                                                        • 2 BR
                                                                        • 2 BA
                                                                        • Sleeps 5
                                                                        14
                                                                          NEW!
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • Sleeps 8
                                                                            NEW!
                                                                            • 6 BR
                                                                            • 4 BA
                                                                            • Sleeps 14
                                                                            1 Review
                                                                              • 4 BR
                                                                              • 2 BA
                                                                              • Sleeps 8
                                                                                • 4 BR
                                                                                • 4 BA
                                                                                • Sleeps 10
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 3
                                                                                  2 Reviews
                                                                                    • 5 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 10
                                                                                    8
                                                                                      • 3 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 12
                                                                                      29
                                                                                        • 4 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 10
                                                                                        2 Reviews
                                                                                          • 8 BR
                                                                                          • 8 BA
                                                                                          • Sleeps 4
                                                                                            NEW!
                                                                                            • 4 BR
                                                                                            • 4 BA
                                                                                            • Sleeps 8
                                                                                              NEW!
                                                                                              • 1 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 10
                                                                                                • 4 BR
                                                                                                • 4 BA
                                                                                                • Sleeps 8
                                                                                                25
                                                                                                  • 3 BR
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                                                                                                  • Sleeps 7
                                                                                                  4
                                                                                                    • 5 BR
                                                                                                    • 3 BA
                                                                                                    • 1 HF BA
                                                                                                    • Sleeps 15
                                                                                                    1 Review
                                                                                                      • 11 BR
                                                                                                      • 8 BA
                                                                                                      • 1 HF BA
                                                                                                      • Sleeps 27
                                                                                                      1 Review
                                                                                                      • 1 - 50 of 56
                                                                                                       

                                                                                                      Recent Chestertown Reviews

                                                                                                      Absolutely Breathtakingly Beautiful!!

                                                                                                      5 of 5
                                                                                                      I would HIGHLY recommend this Lodge. The place is ABSOLUTELY GORGEOUS! It is extremely clean and the Owners are Wonderful people. The Lodge has everything you could want....Waterfront views, privacy, beautiful spacious rooms, oversized dining room for all to sit and eat together. Multiple bathrooms for everyone to have their own space, comfortable beds and beautiful sitting areas. If you couldn't ask for more there is a bar inside for entertaining and a game room so everyone can gather around and shoot pool and have a good time. We had a wonderful time sitting on the back deck that overlooks the water and relaxed and had drinks and listened to music. This place is definitely a MUST SEE!!
                                                                                                      • Submitted: Aug 18, 2016
                                                                                                      • Stayed: Jul 2016

                                                                                                      Delightful Vacation Home...

                                                                                                      5 of 5
                                                                                                      Booking this property was somewhat of a shot-in-the-dark as my family and I had almost no familiarity with the Eastern Shore of MD. Nevertheless, the owners were incredibly responsive and helpful from the time we were considering booking the house all the way up through our stay. The house has an awesome location with bay views from the porch and a few minute walk to a lookout point and the beach. The house itself was very charming and clean as well. Even though we were at max capacity, it never felt crowded because the rooms downstairs are large and spacious. Having AC over the period we were there was also a huge plus as it was very hot!! If you are looking for a charming beach house that can fit a small crowd, this is the place! It's even stocked with beach gear and a grill. The neighborhood surrounding the house is quite scenic as well and perfect for taking an afternoon or morning stroll/jog. If we decide to vacation on the Eastern Shore, we will definitely try to rent this house again. Thanks Lucia and Ben!
                                                                                                      • Submitted: Aug 16, 2016
                                                                                                      • Stayed: Jul 2016

                                                                                                      We had a wonderful, stress-free experience in the cottage with its view upon the Chesapeak Bay.

                                                                                                      5 of 5
                                                                                                      The property is clean and well maintained. Francesca and her family were helpful and quite giving as they made certain that we were comfortable. Their community connectivity served us well as they provided us with information about a variety of activities taking place in the surrounding towns, and access to a wonderful play that's now premiering in NY. Overall we highly recommend this property to those just needing to get off of life's treadmill!
                                                                                                      • Submitted: Aug 13, 2016
                                                                                                      • Stayed: Aug 2016