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Chesapeake Bay Vacation Rentals(136)

136 Results
Book it Now!
3 - 7 night minimum stay
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 18
    (16)
    2 - 3 night minimum stay
    • 4 BR,
    • 2 BA,
    • 1 HF BA,
    • Sleeps 8
      (30)
      3 - 7 night minimum stay
      • 4 BR,
      • 4 BA,
      • Sleeps 8
        (30)
        Book it Now!
        3 - 7 night minimum stay
        • 4 BR,
        • 2 BA,
        • Sleeps 9
          (22)
          Book it Now!
          2 night minimum stay
          • 3 BR,
          • 2 BA,
          • Sleeps 6
            (7)
            2 - 3 night minimum stay
            • 7 BR,
            • 4 BA,
            • 2 HF BA,
            • Sleeps 20
              (8)
              Book it Now!
              2 night minimum stay
              • 2 BR,
              • 2 BA,
              • Sleeps 6
                (3)
                $350 - $450
                per night
                2 - 5 night minimum stay
                • 3 BR,
                • 2 BA,
                • Sleeps 8
                  (14)
                  2 - 3 night minimum stay
                  • 6 BR,
                  • 5 BA,
                  • 1 HF BA,
                  • Sleeps 12
                    (5)
                    2 night minimum stay
                    • 4 BR,
                    • 4 BA,
                    • 1 HF BA,
                    • Sleeps 10
                      2 Reviews
                      • 3 BR,
                      • 2 BA,
                      • Sleeps 6
                        (7)
                        Book it Now!
                        2 - 7 night minimum stay
                        • 6 BR,
                        • 6 BA,
                        • Sleeps 13
                          (14)
                          2 night minimum stay
                          • 4 BR,
                          • 4 BA,
                          • Sleeps 8
                            (15)
                            Book it Now!
                            3 night minimum stay
                            • 4 BR,
                            • 3 BA,
                            • 1 HF BA,
                            • Sleeps 11
                              (5)
                              2 - 7 night minimum stay
                              • 3 BR,
                              • 2 BA,
                              • Sleeps 8
                                (11)
                                Book it Now!
                                2 - 3 night minimum stay
                                • 6 BR,
                                • 5 BA,
                                • 1 HF BA,
                                • Sleeps 12
                                  1 Review
                                  Book it Now!
                                  3 night minimum stay
                                  • 5 BR,
                                  • 3 BA,
                                  • Sleeps 12
                                    1 Review
                                    • 4 BR,
                                    • 2 BA,
                                    • 1 HF BA,
                                    • Sleeps 8
                                      (10)
                                      2 - 7 night minimum stay
                                      • 4 BR,
                                      • 3 BA,
                                      • Sleeps 10
                                        (25)
                                        Book it Now!
                                        1 - 3 night minimum stay
                                        • 2 BR,
                                        • 1 BA,
                                        • Sleeps 6
                                          2 Reviews
                                          Book it Now!
                                          • 2 BR,
                                          • 1 BA,
                                          • 1 HF BA,
                                          • Sleeps 4
                                            2 - 4 night minimum stay
                                            • 4 BR,
                                            • 2 BA,
                                            • 1 HF BA,
                                            • Sleeps 12
                                              (25)
                                              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
                                                  (12)
                                                  7 night minimum stay
                                                  • 4 BR,
                                                  • 3 BA,
                                                  • Sleeps 12
                                                    (12)
                                                    • 4 BR,
                                                    • 2 BA,
                                                    • Sleeps 10
                                                      (7)
                                                      2 - 7 night minimum stay
                                                      • 2 BR,
                                                      • 1 BA,
                                                      • Sleeps 6
                                                        (8)
                                                        Book it Now!
                                                        2 - 7 night minimum stay
                                                        • 4 BR,
                                                        • 3 BA,
                                                        • Sleeps 10
                                                          (16)
                                                          Book it Now!
                                                          1 - 2 night minimum stay
                                                          • 1 BR,
                                                          • 1 BA,
                                                          • Sleeps 3
                                                            (17)
                                                             

                                                            Recent Chesapeake Bay Reviews

                                                            AMAZING PRIVATE BEACH HOME WITH SPECTACULAR VIEWS!

                                                            5 of 5
                                                            My family, friends and I were unfortunately only able to stay for a long weekend at this spectacular property due conflicting work schedules, but a long weekend was all it took to keep us wanting to come back for summers to come! The owners did a wonderful job providing us with all the comforts of home, an updated kitchen with granite counter tops, stainless steal appliances and updated bathrooms with amazing tile work. The outside the property could handle any family gathering with a view that would leave you speechless. The property faces west allowing you catch the sun setting over the Chesapeake from either the brand new deck they installed, from the water front or from the wide open back yard. All day and night we took advantage of the great outdoors, barbecuing, eating crabs, fresh seafood, swimming, playing catch, Frisbee, fishing and a fire pit at night to roast marshmallows, make s’mores and just to hang out. The property also boasts a private beach access that stretches for at least a quarter of a mile, allowing you direct access for swimming and water sports. Last but not least the owners of this property were more then accommodating throughout the entire rental process, they went above beyond to make us feel at home and to make our stay incredible! They provided all the information you could need about the surrounding area, grocery stores, restaurants, places that have live music, places to rent water crafts, the night life, but I assure you once see the property you will never want to leave. I would recommend this property for anyone who would love the privacy of a 10 acre property, with private beach access, all the comforts of home and a view that would keep you coming back. Thank you so much for allowing us to stay in your wonderful home, we look forward to staying with you in the future and next time we’ll make all the necessary arrangements to be able to stay the week.
                                                            • Submitted: Aug 20, 2014
                                                            • Stayed: Jul 2014

                                                            Perfect getaway filled with warmth and hospitality

                                                            5 of 5
                                                            My sister is getting married this winter so a few of the bridesmaids and I planned a getaway weekend for her. It was the everything we hoped for - a nice relaxing weekend with the girls to unwind and get away from the stresses of life and wedding planning. The hideaway was beautiful and so comfortable inside and the neighborhood was so friendly we really felt at home. One of the many great things about the property is the proximity to the bay. It was awesome to sit outside on the patio in the morning and be able to see the water and listen to the waves. The beaches were so close to the house and I couldn't believe how warm the bay water was! We didn't do a whole lot while we were there - mostly just hung out on the beaches and on the water (I couldn't believe how warm the bay water was!) but everywhere we went we were welcomed with so much hospitality! We ate at Jerry's place the first day and since we had never been there, our server brought out samples for us to try some of their more popular menu options. It was the best restaurant service I have ever experienced that wasn't a white glove restaurant. We went to a wine tasting at Perigeaux Vineyards and they went out of their way to make us feel comfortable and give us the most fantastic fun experience. They recommended we go to Stoney's for dinner (only about 15 min from the winery) where we, again, had an awesome server who we became quick friends with. Overall, it was the best vacation we could have wished for. Nobody wanted to leave. We will definitely be back!
                                                            • Submitted: Aug 13, 2014
                                                            • Stayed: Aug 2014

                                                            Great get away!

                                                            5 of 5
                                                            This house is just what my husband and I were looking for! Comfort and privacy with an amazing water view. The large kitchen and River Room were wonderful, as was the very spacious master bedroom with windows looking out on the Harris Creek. We spent a lot of time on the dock (reading, eating, swimming, etc.) and loved the fact that we had such a big yard with so much privacy. The house is very close to St. Michael's, where we went often for dinner, shopping, etc. during the week that we were there. We loved using the kayaks off of the dock. There were no bicycles, but I do not think that we would have wanted to bike on the busy roads anyway. Although there were just two of us, the house really has 4 bedrooms (counting the sleeping loft) and it would have easily accommodated more people. If you rent this home, you will not be sorry - it is beautiful!
                                                            • Submitted: Aug 12, 2014
                                                            • Stayed: Jul 2014