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Chesapeake Bay: Houses, Cottages & More (391)

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    • 2 BR
    • 2 BA
    • Sleeps 6
    13
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      • 3 BA
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      17
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        5
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          • 4 BA
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          49
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            • 6 BA
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            32
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              • 8 BR
              • 7 BA
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              21
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                    • Sleeps 10
                    52
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                      • 3 BR
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                      6
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                        • 3 BR
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                        19
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                          • 4 BR
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                          51
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                            • 4 BR
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                            • Sleeps 16
                            13
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                              • 7 BR
                              • 4 BA
                              • 1 HF BA
                              • Sleeps 14
                              3
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                                • 12 BR
                                • 8 BA
                                • 1 HF BA
                                • Sleeps 40
                                22
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                                  • 4 BR
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                                    • 6 BR
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                                    • Sleeps 12
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                                      • 4 BR
                                      • 4 BA
                                      • 1 HF BA
                                      • Sleeps 10
                                      16
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                                        • 3 BR
                                        • 2 BA
                                        • Sleeps 6
                                        51
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                                          • 4 BR
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                                          • Sleeps 8
                                          20
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                                            • 4 BR
                                            • 2 BA
                                            • Sleeps 9
                                            26
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                                              • 3 BR
                                              • 3 BA
                                              • Sleeps 6
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                                                • 7 BR
                                                • 5 BA
                                                • 1 HF BA
                                                • Sleeps 22
                                                44
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                                                  • 6 BR
                                                  • 5 BA
                                                  • 1 HF BA
                                                  • Sleeps 12
                                                  8
                                                    • 3 BR
                                                    • 2 BA
                                                    • Sleeps 9
                                                    9
                                                      • 2 BR
                                                      • 2 BA
                                                      • Sleeps 4
                                                      40
                                                        • 7 BR
                                                        • 6 BA
                                                        • 1 HF BA
                                                        • Sleeps 28
                                                        14
                                                          • 7 BR
                                                          • 4 BA
                                                          • 2 HF BA
                                                          • Sleeps 20
                                                          20
                                                            • 5 BR
                                                            • 3 BA
                                                            • 1 HF BA
                                                            • Sleeps 18
                                                            10
                                                              • 4 BR
                                                              • 4 BA
                                                              • Sleeps 8
                                                              9
                                                              • 1 - 30 of 391
                                                               

                                                              Recent Chesapeake Bay Reviews

                                                              Shoreline on 3 sides of property, everything you need

                                                              5 of 5
                                                              This beautiful mansion has views of the water on three sides of the property so there are relaxing views from every window in the house. There's plenty of kitchen room and all of the equipment for some serious cooking. The interiors are spacious and well furnished but not fussy. We were there with 16 adults and 5 babies and it was perfect for us. In the day time we hiked, cooked and hung out in the large living areas. In the evenings we lit a fire in the pit and sat by the water. This is the 13th year my friends have had a reunion and everyone said this was the best house yet. The trip from the Baltimore airport is about 2 hours so make sure to factor in enough time. It's definitely remote but that's part of what makes it so special. A real escape. Thanks to the owner for his excellent communication and checking in, despite some HomeAway technical difficulties which were not in his control. I felt very welcome in his home. The caretaker was also very kind and helpful.
                                                              • Submitted: Apr 22, 2016
                                                              • Stayed: Mar 2016

                                                              "Perfect"

                                                              5 of 5
                                                              Our first stay in St. Michaels and at the Harbor Hideaway was on Super Bowl weekend and we had a fantastic time! The house was very clean, comfortable and welcoming. Everything we needed was there, full stocked kitchen, nice TV's, two grills, bikes and a fire pit out back. The house is within walking distance to everything in town and to the harbor area. The shops were all open and had great sales this time of year--my sister and I took advantage of this while our husbands hung out in the pubs. We ate at Ava's Pizzeria for lunch one day and to Gina's Café (right at the top of our street) and the food and drink was fantastic at both places. We had dinner one night at Bistro--we thought it was just average (pricey)--should have gone to Theo's instead. One morning we drove over to Tilghman Island and had breakfast at Two If By Sea--fantastic! It was worth the drive! We did not make it to the museum so we are planning a trip back to St. Michaels to keep exploring and we will defiantly stay at the Harbor Hideaway!! Carol thank you for such a welcome and wonderful stay!!
                                                              • Submitted: Feb 24, 2016
                                                              • Stayed: Feb 2016

                                                              Wedding Celebration

                                                              5 of 5
                                                              Go. Stay. Here. You will love it. Enough said.
                                                              • Submitted: Jan 24, 2016
                                                              • Stayed: Jan 2016