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Chestertown: House Rentals (148)

  • 1 - 50 of 148
Additional fees apply. Taxes may be added.
    • 3 BR
    • 2 BA
    • Sleeps 6
    3
      • 3 BR
      • 2 BA
      • Sleeps 6
      9
        • 2 BR
        • 2 BA
        • Sleeps 5
        2 Reviews
          NEW!
          • 3 BR
          • 1 BA
          • 1 HF BA
          • Sleeps 6
            • 2 BR
            • 1 BA
            • 1 HF BA
            • Sleeps 6
            23
              • 5 BR
              • 4 BA
              • 1 HF BA
              • Sleeps 10
              3
                • 3 BR
                • 1 BA
                • 1 HF BA
                • Sleeps 7
                29
                  • 3 BR
                  • 3 BA
                  • Sleeps 8
                  39
                    • 2 BR
                    • 1 BA
                    • 1 HF BA
                    • Sleeps 4
                    8
                      • 5 BR
                      • 3 BA
                      • Sleeps 8
                      5
                        • 3 BR
                        • 2 BA
                        • 1 HF BA
                        • Sleeps 8
                        3
                          • 4 BR
                          • 2 BA
                          • 1 HF BA
                          • Sleeps 11
                            • 4 BR
                            • 2 BA
                            • Sleeps 10
                            9
                              • 2 BR
                              • 1 BA
                              • Sleeps 5
                              1 Review
                                NEW!
                                • 5 BR
                                • 4 BA
                                • Sleeps 11
                                  • 4 BR
                                  • 2 BA
                                  • Sleeps 10
                                  14
                                    • 3 BR
                                    • 2 BA
                                    • Sleeps 9
                                    8
                                      • 4 BR
                                      • 2 BA
                                      • Sleeps 12
                                      19
                                        • 6 BR
                                        • 2 BA
                                        • Sleeps 11
                                        13
                                          • 3 BR
                                          • 2 BA
                                          • 1 HF BA
                                          • Sleeps 8
                                          2 Reviews
                                            • 3 BR
                                            • 1 BA
                                            • 1 HF BA
                                            • Sleeps 8
                                            10
                                              • 3 BR
                                              • 1 BA
                                              • Sleeps 8
                                                • 2 BR
                                                • 1 BA
                                                • Sleeps 6
                                                18
                                                  • 2 BR
                                                  • 1 BA
                                                  • Sleeps 6
                                                  1 Review
                                                    • 4 BR
                                                    • 2 BA
                                                    • Sleeps 8
                                                      NEW!
                                                      • 3 BR
                                                      • 1 BA
                                                      • Sleeps 6
                                                        • 4 BR
                                                        • 4 BA
                                                        • Sleeps 10
                                                          • 3 BR
                                                          • 1 BA
                                                          • Sleeps 12
                                                          29
                                                            • 5 BR
                                                            • 3 BA
                                                            • Sleeps 12
                                                            12
                                                              • 5 BR
                                                              • 3 BA
                                                              • Sleeps 10
                                                              15
                                                                • 3 BR
                                                                • 3 BA
                                                                • Sleeps 8
                                                                12
                                                                  • 2 BR
                                                                  • 1 BA
                                                                  • 1 HF BA
                                                                  • Sleeps 5
                                                                  28
                                                                    • 2 BR
                                                                    • 2 BA
                                                                    • Sleeps 6
                                                                    2 Reviews
                                                                      • 2 BR
                                                                      • 2 BA
                                                                      • Sleeps 6
                                                                      8
                                                                        • 4 BR
                                                                        • 2 BA
                                                                        • Sleeps 11
                                                                        7
                                                                          • 2 BR
                                                                          • 1 BA
                                                                          • Sleeps 6
                                                                          7
                                                                            • 3 BR
                                                                            • 2 BA
                                                                            • 1 HF BA
                                                                            • Sleeps 8
                                                                            7
                                                                              • 3 BR
                                                                              • 4 BA
                                                                              • Sleeps 8
                                                                              10
                                                                                • 2 BR
                                                                                • 2 BA
                                                                                • 1 HF BA
                                                                                • Sleeps 6
                                                                                14
                                                                                  • 5 BR
                                                                                  • 4 BA
                                                                                  • 1 HF BA
                                                                                  • Sleeps 16
                                                                                  4
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • 1 HF BA
                                                                                    • Sleeps 8
                                                                                    2 Reviews
                                                                                      • 1 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 4
                                                                                      1 Review
                                                                                        • 5 BR
                                                                                        • 3 BA
                                                                                        • Sleeps 14
                                                                                        17
                                                                                          • 3 BR
                                                                                          • 3 BA
                                                                                          • Sleeps 6
                                                                                          2 Reviews
                                                                                            • 3 BR
                                                                                            • 3 BA
                                                                                            • Sleeps 8
                                                                                            12
                                                                                              • 3 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 8
                                                                                              1 Review
                                                                                                • 5 BR
                                                                                                • 4 BA
                                                                                                • 1 HF BA
                                                                                                • Sleeps 12
                                                                                                11
                                                                                                  • 4 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 10
                                                                                                  2 Reviews
                                                                                                    • 5 BR
                                                                                                    • 4 BA
                                                                                                    • Sleeps 18
                                                                                                    14
                                                                                                      • 4 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 9
                                                                                                      8
                                                                                                      • 1 - 50 of 148
                                                                                                       

                                                                                                      Recent Chestertown Reviews

                                                                                                      Perfection!!

                                                                                                      5 of 5
                                                                                                      My daughter, granddaughter and I thoroughly enjoyed our long weekend at the Captain's Cottage! The house is decorated beautifully, is very clean, and the view of the marina is incredible! We drank our morning coffee on the deck as we watched the sailboats leave for the bay! The little girls really enjoyed the marina pool, and the café was very convenient! We were only minutes away from downtown where we toured the Naval Academy, ate crab cakes at the Iron Rooster, and I had my first ever lobster roll at Mason's............everything I thought it would be and more! We will definitely be back!! Thanks to Stephanie for being so helpful with the reservations!
                                                                                                      • Submitted: Aug 31, 2016
                                                                                                      • Stayed: Aug 2016

                                                                                                      A good stay

                                                                                                      4 of 5
                                                                                                      It was a good stay for our group. Plenty of rooms, spaces, and a near by beach. But the house was not clean enough and many things to fix. But again, it was appropriate for our group's gathering not far ways from MD and PA area. I appreciate the owner(s) for making this place available.
                                                                                                      • Submitted: Aug 22, 2016
                                                                                                      • Stayed: Aug 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