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Chesapeake Bay Vacation Home Rentals(125)

125 Results
Book it Now!
3 - 7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 9
    (25)
    Book it Now!
    3 - 7 night minimum stay
    • 6 BR,
    • 5 BA,
    • 1 HF BA,
    • Sleeps 16
      (16)
      2 - 3 night minimum stay
      • 4 BR,
      • 2 BA,
      • 1 HF BA,
      • Sleeps 8
        (32)
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        3 night minimum stay
        • 4 BR,
        • 2 BA,
        • Sleeps 16
          (9)
          $350 - $425
          per night
          2 - 5 night minimum stay
          • 3 BR,
          • 2 BA,
          • Sleeps 8
            (14)
            3 - 7 night minimum stay
            • 5 BR,
            • 3 BA,
            • 1 HF BA,
            • Sleeps 18
              (9)
              3 - 7 night minimum stay
              • 4 BR,
              • 3 BA,
              • 1 HF BA,
              • Sleeps 8
                2 Reviews
                Book it Now!
                3 night minimum stay
                • 4 BR,
                • 3 BA,
                • 1 HF BA,
                • Sleeps 11
                  (7)
                  2 night minimum stay
                  • 4 BR,
                  • 4 BA,
                  • Sleeps 8
                    (15)
                    2 - 7 night minimum stay
                    • 3 BR,
                    • 2 BA,
                    • Sleeps 8
                      (11)
                      Book it Now!
                      3 night minimum stay
                      • 5 BR,
                      • 3 BA,
                      • Sleeps 12
                        2 Reviews
                        3 - 7 night minimum stay
                        • 7 BR,
                        • 3 BA,
                        • 1 HF BA,
                        • Sleeps 18
                          (7)
                          2 - 7 night minimum stay
                          • 4 BR,
                          • 3 BA,
                          • Sleeps 8
                            1 Review
                            • 3 BR,
                            • 2 BA,
                            • Sleeps 9
                              1 Review
                              3 - 7 night minimum stay
                              • 6 BR,
                              • 3 BA,
                              • Sleeps 12
                                (3)
                                3 - 7 night minimum stay
                                • 6 BR,
                                • 5 BA,
                                • 1 HF BA,
                                • Sleeps 15
                                  (7)
                                  3 - 4 night minimum stay
                                  • 4 BR,
                                  • 2 BA,
                                  • 1 HF BA,
                                  • Sleeps 9
                                    (9)
                                    Book it Now!
                                    2 night minimum stay
                                    • 3 BR,
                                    • 2 BA,
                                    • Sleeps 8
                                      (26)
                                      2 - 7 night minimum stay
                                      • 5 BR,
                                      • 4 BA,
                                      • Sleeps 10
                                        (14)
                                        7 night minimum stay
                                        • 4 BR,
                                        • 3 BA,
                                        • Sleeps 12
                                          (12)
                                          • 4 BR,
                                          • 2 BA,
                                          • Sleeps 10
                                            (8)
                                            2 - 3 night minimum stay
                                            • 3 BR,
                                            • 3 BA,
                                            • 1 HF BA,
                                            • Sleeps 8
                                              (12)
                                              2 - 7 night minimum stay
                                              • 8 BR,
                                              • 6 BA,
                                              • Sleeps 22
                                                (19)
                                                • 3 BR,
                                                • 2 BA,
                                                • Sleeps 6
                                                  (5)
                                                  Book it Now!
                                                  2 - 7 night minimum stay
                                                  • 4 BR,
                                                  • 3 BA,
                                                  • Sleeps 10
                                                    (17)
                                                    Book it Now!
                                                    2 - 7 night minimum stay
                                                    • 4 BR,
                                                    • 3 BA,
                                                    • Sleeps 12
                                                      (36)
                                                      Book it Now!
                                                      2 night minimum stay
                                                      • 3 BR,
                                                      • 2 BA,
                                                      • 1 HF BA,
                                                      • Sleeps 9
                                                        (12)
                                                        $200 - $350
                                                        per night
                                                        Book it Now!
                                                        2 night minimum stay
                                                        • 2 BR,
                                                        • 1 BA,
                                                        • 1 HF BA,
                                                        • Sleeps 8
                                                          (8)
                                                          2 - 6 night minimum stay
                                                          • 2 BR,
                                                          • 1 BA,
                                                          • Sleeps 5
                                                            (25)
                                                            Book it Now!
                                                            7 night minimum stay
                                                            • 4 BR,
                                                            • 2 BA,
                                                            • Sleeps 12
                                                              (4)
                                                               

                                                              Recent Chesapeake Bay Reviews

                                                              Waterfront Retreat

                                                              5 of 5
                                                              If you enjoy water related activities in a tranquil setting then this is a must rental. We towed our boat from Ohio and launched it across the creek from the property. The dock easily accommodates boats of varying sizes. We were able to enjoy cruising around the picturesque creek which has easy access to the Bay. The crabbing was excellent and we had steamed crabs every night during our stay. Phil and Stephanie were very accommodating and the house was clean and well maintained. Every summer we rent waterfront homes in Maryland and I can honestly state that this was one of our best rentals.
                                                              • Submitted: Sep 9, 2014
                                                              • Stayed: Aug 2014

                                                              Perfect Weekend getaway!

                                                              5 of 5
                                                              Our family had a wonderful Labor day weekend at "Sandy Pines". The home was clean and well maintained. The owners and caretakers were very easy to work with. We fished, crabbed, kayaked, biked and swam the entire weekend that we did not even go to St. Michaels until the day we were leaving. When we return to the Chesapeake , we will be renting Sandy Pines again.
                                                              • Submitted: Sep 8, 2014
                                                              • Stayed: Sep 2014

                                                              Jewel of St. Michael's. A wonderful home!!!

                                                              5 of 5
                                                              After hours of searching on VBRO/HomeAway and visiting several rental homes in St. Michael’s and the surrounding area we came upon a jewel. That jewel was Misbayhaven!!! We spent a week there in August 2014 with our extended family which consisted of 5 adults and 4 children ages 7 to 9. The owner Debbie was so accommodating, personable and was truly a pleasure to work with. So much better than working directly with a rental company. The home was beautifully decorated; the kitchen was spacious and had everything we could possibly need. There was enough space for the entire family to spread out (large TV room and plenty of games and videos for the kids). The bedrooms had beautiful views of the water and mattresses were very comfortable. We took the linen package and that made packing much easier. The screened in porch was so spacious and it kept the bugs away. We enjoyed eating our meals out there while we enjoyed the spectacular view of the water. Sunsets were so beautiful. The house was exceptionally clean and we were excited that pets were not allowed because several people in our family are very allergic to dogs. It is a low allergen home!!! Our kids were never bored. They swam in the pool (plenty of pool toys) for hours and the hot tub was a bonus for all. They were so tired that they asked to get to bed early at night. We enjoyed docking our sailboat and crabbing and fishing off the dock. We also enjoyed some pretty fierce ping pong matches in the garage as well. The kids enjoyed the large selection of bikes to ride. So many homes in Cambridge and Oxford that we looked at were so remote and far away from dining or shopping. It is less than a 10 minute ride into St. Michael’s for dinner or an ice cream cone from Misbayhaven. That is a real bonus when you have hungry kids. Misbayhaven was the perfect vacation for our family!! I would highly recommend this home. You will not be disappointed!!!!! You will not want your vacation to end!!
                                                              • Submitted: Sep 5, 2014
                                                              • Stayed: Aug 2014