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  • 301 - 350 of 405
Additional fees apply. Taxes may be added.
    • 3 BR
    • 1 BA
    • Sleeps 6
      View details for price
      • 2 BR
      • 2 BA
      • Sleeps 4
      16
        • 3 BR
        • 2 BA
        • Sleeps 6
        2 Reviews
          • 3 BR
          • 2 BA
          • Sleeps 6
          6
            $310
            avg/night
            • 3 BR
            • 2 BA
            • Sleeps 6
            10
              $360
              avg/night
              • 4 BR
              • 2 BA
              • 1 HF BA
              • Sleeps 13
              5
                • 6 BR
                • 4 BA
                • 2 HF BA
                • Sleeps 16
                20
                  • 3 BR
                  • 2 BA
                  • Sleeps 6
                  9
                    • 6 BR
                    • 4 BA
                    • 1 HF BA
                    • Sleeps 11
                    9
                      • 6 BR
                      • 4 BA
                      • 1 HF BA
                      • Sleeps 12
                      14
                        $257
                        avg/night
                        • 2 BR
                        • 1 BA
                        • Sleeps 6
                        15
                          • 5 BR
                          • 3 BA
                          • 1 HF BA
                          • Sleeps 11
                          28
                            $229
                            avg/night
                            • 3 BR
                            • 2 BA
                            • 1 HF BA
                            • Sleeps 6
                            18
                              • 4 BR
                              • 3 BA
                              • Sleeps 10
                              17
                                • 3 BR
                                • 3 BA
                                • 1 HF BA
                                • Sleeps 8
                                14
                                  $300
                                  avg/night
                                  • 3 BR
                                  • 3 BA
                                  • Sleeps 8
                                  4
                                    • 4 BR
                                    • 2 BA
                                    • Sleeps 8
                                    16
                                      • 2 BR
                                      • 1 BA
                                      • Sleeps 6
                                      3
                                        • 3 BR
                                        • 2 BA
                                        • Sleeps 8
                                        3
                                          • 5 BR
                                          • 4 BA
                                          • Sleeps 14
                                          4
                                            • 3 BR
                                            • 3 BA
                                            • Sleeps 8
                                            3
                                              • 5 BR
                                              • 3 BA
                                              • Sleeps 12
                                              28
                                                • 3 BR
                                                • 1 BA
                                                • Sleeps 6
                                                4
                                                  • 3 BR
                                                  • 2 BA
                                                  • Sleeps 7
                                                  90
                                                    • 3 BR
                                                    • 2 BA
                                                    • Sleeps 8
                                                    6
                                                      • 5 BR
                                                      • 2 BA
                                                      • 1 HF BA
                                                      • Sleeps 16
                                                        • 5 BR
                                                        • 2 BA
                                                        • Sleeps 15
                                                        29
                                                          • 4 BR
                                                          • 1 BA
                                                          • Sleeps 8
                                                          9
                                                            • 3 BR
                                                            • 2 BA
                                                            • Sleeps 6
                                                            1 Review
                                                              • 2 BR
                                                              • 2 BA
                                                              • Sleeps 6
                                                              3
                                                                • 2 BR
                                                                • 1 BA
                                                                • Sleeps 6
                                                                5
                                                                  • 5 BR
                                                                  • 3 BA
                                                                  • Sleeps 11
                                                                    • 3 BR
                                                                    • 3 BA
                                                                    • Sleeps 12
                                                                    33
                                                                      • 5 BR
                                                                      • 3 BA
                                                                      • Sleeps 18
                                                                      21
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • Sleeps 7
                                                                        18
                                                                          • 4 BR
                                                                          • 3 BA
                                                                          • Sleeps 10
                                                                          9
                                                                            • 2 BR
                                                                            • 2 BA
                                                                            • Sleeps 6
                                                                            4
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • 1 HF BA
                                                                              • Sleeps 8
                                                                              1 Review
                                                                                • 4 BR
                                                                                • 2 BA
                                                                                • Sleeps 10
                                                                                12
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 8
                                                                                  14
                                                                                    • 5 BR
                                                                                    • 5 BA
                                                                                    • 1 HF BA
                                                                                    • Sleeps 10
                                                                                    5
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 6
                                                                                      19
                                                                                        • 6 BR
                                                                                        • 5 BA
                                                                                        • Sleeps 20
                                                                                        11
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 6
                                                                                          4
                                                                                            • 4 BR
                                                                                            • 4 BA
                                                                                            • Sleeps 8
                                                                                            25
                                                                                              • 3 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 6
                                                                                              18
                                                                                                • 6 BR
                                                                                                • 5 BA
                                                                                                • Sleeps 12
                                                                                                1 Review
                                                                                                  • 7 BR
                                                                                                  • 6 BA
                                                                                                  • Sleeps 16
                                                                                                  9
                                                                                                    • 4 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 10
                                                                                                    7
                                                                                                      • 4 BR
                                                                                                      • 3 BA
                                                                                                      • Sleeps 13
                                                                                                      26
                                                                                                      • 301 - 350 of 405
                                                                                                       

                                                                                                      Recent Chesapeake Bay Reviews

                                                                                                      Beautiful property for a weekend with friends!

                                                                                                      5 of 5
                                                                                                      We rented this beautiful property for Memorial Day Weekend 2015. It was great for our group, which included a number of couples, some with children, some without. The layout allowed us to put the families on one side of the house, while those of us without kids slept on the other to avoid getting woken up in the morning! The kids in particular loved the beach and the huge yard.
                                                                                                      • Submitted: Jun 22, 2016
                                                                                                      • Stayed: May 2016

                                                                                                      Simply amazing!

                                                                                                      5 of 5
                                                                                                      We stayed here at Chip and Gayle's paradise for our Niece's wedding in Charlestown. This house is very beautifully decorated a a very comfortable place to stay. Very clean and complete. Would recommend this place very highly to anyone! Thank you Gayle!
                                                                                                      • Submitted: Jun 20, 2016
                                                                                                      • Stayed: Jun 2016

                                                                                                      Relaxing Summer Retreat!

                                                                                                      5 of 5
                                                                                                      We had a fantastic week here. The property is beautiful and the layout is very conducive to alone time. We had three families and each of us felt very comfortable in our own space. The kids loved catching crabs and fish off of the dock. The pool was clean and well maintained and we spent a lot of time in it. The views are amazing and the kitchen was well stocked. We thoroughly enjoyed our time here. We'll be back!
                                                                                                      • Submitted: Feb 25, 2016
                                                                                                      • Stayed: Aug 2015