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Chesapeake Bay Long Term Vacation Rentals(105)

105 Results
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)
      2 - 3 night minimum stay
      • 6 BR,
      • 5 BA,
      • 1 HF BA,
      • Sleeps 12
        (5)
        • 3 BR,
        • 2 BA,
        • Sleeps 8
          (7)
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          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)
              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 night minimum stay
                    • 5 BR,
                    • 7 BA,
                    • Sleeps 10
                      (13)
                      2 - 7 night minimum stay
                      • 4 BR,
                      • 3 BA,
                      • Sleeps 10
                        (25)
                        2 night minimum stay
                        • 4 BR,
                        • 2 BA,
                        • 1 HF BA,
                        • Sleeps 8
                          (11)
                          Book it Now!
                          1 - 3 night minimum stay
                          • 2 BR,
                          • 1 BA,
                          • Sleeps 6
                            2 Reviews
                            2 - 3 night minimum stay
                            • 3 BR,
                            • 2 BA,
                            • 1 HF BA,
                            • Sleeps 9
                              (11)
                              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)
                                  2 - 3 night minimum stay
                                  • 3 BR,
                                  • 3 BA,
                                  • 1 HF BA,
                                  • Sleeps 8
                                    (12)
                                    2 - 3 night minimum stay
                                    • 4 BR,
                                    • 4 BA,
                                    • 2 HF BA,
                                    • Sleeps 10
                                      2 Reviews
                                      3 night minimum stay
                                      • 2 BR,
                                      • 1 BA,
                                      • Sleeps 5
                                        (12)
                                        2 night minimum stay
                                        • 3 BR,
                                        • 3 BA,
                                        • Sleeps 6
                                          (7)
                                          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)
                                              Book it Now!
                                              3 - 7 night minimum stay
                                              • 3 BR,
                                              • 1 BA,
                                              • Sleeps 6
                                                (10)
                                                3 night minimum stay
                                                • 2 BR,
                                                • 2 BA,
                                                • Sleeps 6
                                                  (24)
                                                  Book it Now!
                                                  2 night minimum stay
                                                  • 2 BR,
                                                  • 1 BA,
                                                  • Sleeps 6
                                                    (6)
                                                    Book it Now!
                                                    7 night minimum stay
                                                    • 4 BR,
                                                    • 2 BA,
                                                    • Sleeps 12
                                                      (4)
                                                      2 - 6 night minimum stay
                                                      • 2 BR,
                                                      • 1 BA,
                                                      • Sleeps 5
                                                        (25)
                                                        Book it Now!
                                                        2 - 7 night minimum stay
                                                        • 3 BR,
                                                        • 2 BA,
                                                        • Sleeps 6
                                                          (8)
                                                          Book it Now!
                                                          2 night minimum stay
                                                          • 5 BR,
                                                          • 5 BA,
                                                          • Sleeps 10
                                                            (3)
                                                             

                                                            Recent Chesapeake Bay Reviews

                                                            LOVED IT!!!!! Highly recommend, will return.

                                                            5 of 5
                                                            This property made me a hero with my spouse! Every single detail was well above and beyond the standard for this price range. Even before we arrived our hosts helped us arrange pet sitting for our dog during the days we would be out exploring the area. The location turned out to be perfect and right in the center of all the areas we wanted to explore. The apartment was lovely with great big picture windows to see out to the woods and the beautiful river. It is apparent that the owners put a lot of thought into guests comfort to insure all of our needs were met. The property was clean and well cared for, and felt like an apartment for cherished family members and not a rental. We loved the huge bedrooms! The bed was super comfortable, with pillows in an assortment of softness/firmness. Not only were quality bed linens provided (plenty of extra blankets, and a gorgeous quilt), but kitchen hand towels and bathroom towels were provided and of good quality. We enjoyed swimming in the clean river, which even at low tide had a nice deep channel we could walk out to and enjoy swimming in. In the mornings we would watch the sun rise sitting on the dock with our coffee while our dog swam and wandered the property having the time of her life. We watched herons fish and surveyed the comings and goings of an osprey from a nearby nest. Even though the owners live above the apartment, I recommended this property to friends who are newlywed. The first evening we arrived we laid down just to take a little nap at 6pm and slept for 12 hours straight without hearing a sound. After that one evening we heard some faint footsteps above us - so insignificant when one realizes if this property was a stand alone it would be four times the price. So many little details impressed me about this property – I wish I had written them down as the details have faded after the rest of our trip, but I can tell you we loved it so much that my husband asked if we could please change our spring vacation plans and come back here and we sure plan to. Our dog loved the river apartment so much when we left she dug into the ground and didn’t want to leave, and we felt exactly the same.
                                                            • Submitted: Sep 16, 2014
                                                            • Stayed: Sep 2014

                                                            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

                                                            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