check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar
Cancel Clear Filters Apply Filters

Property Type

Booking Options

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Maryland: Vacation Rental Estates (41)

  • 1 - 41 of 41
Additional fees apply. Taxes may be added.
    • 8 BR
    • 7 BA
    • 2 HF BA
    • Sleeps 20
    24
      Wonderful! 4.9/5
      (24 reviews)
      avg/night
      • 6 BR
      • 3 BA
      • 1 HF BA
      • Sleeps 14
      24
        Wonderful! 4.9/5
        (7 reviews)
        avg/night
        • 8 BR
        • 5 BA
        • Sleeps 12
        7
          Excellent! 4.7/5
          (17 reviews)
          avg/night
          • 3 BR
          • 2 BA
          • 1 HF BA
          • Sleeps 9
          17
            Exceptional! 5.0/5
            (16 reviews)
            avg/night
            • 7 BR
            • 6 BA
            • 1 HF BA
            • Sleeps 28
            16
              • 7 BR
              • 4 BA
              • 2 HF BA
              • Sleeps 20
              29
                • 15 BR
                • 8 BA
                • 2 HF BA
                • Sleeps 48
                7
                  • 6 BR
                  • 6 BA
                  • Sleeps 12
                  19
                    • 6 BR
                    • 3 BA
                    • Sleeps 12
                    2 Reviews
                      • 5 BR
                      • 3 BA
                      • 1 HF BA
                      • Sleeps 10
                      2 Reviews
                        • 5 BR
                        • 4 BA
                        • 1 HF BA
                        • Sleeps 18
                        17
                          • 6 BR
                          • 6 BA
                          • Sleeps 15
                          38
                            • 6 BR
                            • 5 BA
                            • 1 HF BA
                            • Sleeps 12
                            2 Reviews
                              Exceptional! 5.0/5
                              (10 reviews)
                              avg/night
                              • 2 BR
                              • 2 BA
                              • Sleeps 7
                              10
                                • 6 BR
                                • 5 BA
                                • 2 HF BA
                                • Sleeps 12
                                2 Reviews
                                  • 5 BR
                                  • 5 BA
                                  • 1 HF BA
                                  • Sleeps 10
                                  1 Review
                                    • 3 BR
                                    • 3 BA
                                    • Sleeps 6
                                    3
                                      Wonderful! 4.9/5
                                      (8 reviews)
                                      View details for price
                                      • 4 BR
                                      • 4 BA
                                      • 2 HF BA
                                      • Sleeps 10
                                      8
                                        • 8 BR
                                        • 6 BA
                                        • 1 HF BA
                                        • Sleeps 20
                                          • 7 BR
                                          • 4 BA
                                          • 2 HF BA
                                          • Sleeps 20
                                          38
                                            • 4 BR
                                            • 2 BA
                                            • Sleeps 8
                                            12
                                              • 5 BR
                                              • 3 BA
                                              • 1 HF BA
                                              • Sleeps 10
                                              55
                                                • 4 BR
                                                • 2 BA
                                                • Sleeps 12
                                                  • 12 BR
                                                  • 8 BA
                                                  • 1 HF BA
                                                  • Sleeps 40
                                                  28
                                                    • 5 BR
                                                    • 3 BA
                                                    • Sleeps 10
                                                      Wonderful! 4.8/5
                                                      (18 reviews)
                                                      avg/night
                                                      • 4 BR
                                                      • 4 BA
                                                      • 1 HF BA
                                                      • Sleeps 10
                                                      18
                                                        • 6 BR
                                                        • 4 BA
                                                        • Sleeps 14
                                                        1 Review
                                                          Wonderful! 4.9/5
                                                          (14 reviews)
                                                          avg/night
                                                          • 6 BR
                                                          • 5 BA
                                                          • 1 HF BA
                                                          • Sleeps 12
                                                          14
                                                            • 12 BR
                                                            • 7 BA
                                                            • Sleeps 42
                                                            8
                                                              Exceptional! 5.0/5
                                                              (9 reviews)
                                                              avg/night
                                                              • 4 BR
                                                              • 4 BA
                                                              • Sleeps 8
                                                              9
                                                                • 4 BR
                                                                • 4 BA
                                                                • 1 HF BA
                                                                • Sleeps 10
                                                                1 Review
                                                                  • 4 BR
                                                                  • 4 BA
                                                                  • 1 HF BA
                                                                  • Sleeps 12
                                                                  1 Review
                                                                    • 5 BR
                                                                    • 3 BA
                                                                    • Sleeps 10
                                                                    3
                                                                      • 5 BR
                                                                      • 4 BA
                                                                      • 1 HF BA
                                                                      • Sleeps 10
                                                                      1 Review
                                                                        Exceptional! 5.0/5
                                                                        (16 reviews)
                                                                        View details for price
                                                                        • 5 BR
                                                                        • 7 BA
                                                                        • Sleeps 10
                                                                        16
                                                                          • 5 BR
                                                                          • 4 BA
                                                                          • Sleeps 8
                                                                          3
                                                                            • 6 BR
                                                                            • 5 BA
                                                                            • 2 HF BA
                                                                            • Sleeps 12
                                                                            1 Review
                                                                              • 9 BR
                                                                              • 5 BA
                                                                              • 1 HF BA
                                                                              • Sleeps 28
                                                                                • 10 BR
                                                                                • 5 BA
                                                                                • 1 HF BA
                                                                                • Sleeps 26
                                                                                6
                                                                                  • 11 BR
                                                                                  • 8 BA
                                                                                  • 1 HF BA
                                                                                  • Sleeps 27
                                                                                  1 Review
                                                                                    Exceptional! 5.0/5
                                                                                    (6 reviews)
                                                                                    View details for price
                                                                                    • 8 BR
                                                                                    • 6 BA
                                                                                    • 1 HF BA
                                                                                    • Sleeps 15
                                                                                    6
                                                                                    • 1 - 41 of 41
                                                                                     

                                                                                    Recent Maryland Reviews

                                                                                    Just perfect!

                                                                                    5 of 5
                                                                                    Booked the home for my family to stay all together for my daughters wedding weekend at CBMM. Worked out perfectly. Location was close but gave us room to get away from the town and enjoy time with each other. House is meticulously cared for, and we had a lot of comparisons as we had 220 guests attend the wedding staying all over St. Michaels. View was stunning from almost every room. Porch was our favorite. Plenty of room for our full house. All elements pleased the variety of my family members. Well appointed kitchen. Bathrooms at every turn. Large living room for that era. Spaciousness was key. A couch in the living room would've been nice for Sunday football relaxation after a late night wedding. Pool area was perfect. Gorgeous view right on creek. Would definitely return! Felt a bit rushed at checkout. Hard to pack up 4 families at once but I guess rules are rules. Thank you to Jackie and Tina for understanding my family's needs and allowing me to relax about at least one element of a very stressful weekend. I've booked many rental properties and also had rental properties and this was a first class deal!
                                                                                    • Submitted: Sep 30, 2016
                                                                                    • Stayed: Sep 2016

                                                                                    Perfect Staff Getaway

                                                                                    5 of 5
                                                                                    Our team of 10 adults stayed at Eagle Haven for a staff retreat and it was a great experience! The property is beautiful and the home was spacious and comfortable for both group meetings and individual downtime. The kitchen is well equipped for cooking meals. Unfortunately, it rained pretty much the entire time we were there, but we were still able to appreciate and enjoy our beautiful surroundings. We were also thankful that Owen was easily accessible at all times. We would definitely recommend and return to Eagle Haven!
                                                                                    • Submitted: Sep 29, 2016
                                                                                    • Stayed: Sep 2016

                                                                                    Wonderful Labor Day Vacation

                                                                                    5 of 5
                                                                                    I booked the Villa Dun Well as the location to celebrate my sister's 40th birthday and we could not have been more impressed with the space!! The view was out of this world and the activities available on the premises were wonderful from the kayaks to the dock to the salt water pool. We loved it all! Barbara and everyone else involved with the rental were incredibly helpful and attentive to every need and request. The house has the newest appliances and is very convenient to the Tilghman Island restaurants and to St. Michaels. We were sad to leave and could have spent a full week at the Villa with the abundance of things to do. We hope to make the Villa an annual trip and cannot wait to go back!!
                                                                                    • Submitted: Sep 19, 2016
                                                                                    • Stayed: Sep 2016