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Chesapeake Bay Vacation Rental Estates(22)

The Point of It All-Near Annapolis, Washington D.C., Baltimore
    6 Bedrooms,
  • 6 Bathrooms
  • , Sleeps 14
7 night Minimum Stay
  • 6 BR,
  • 6 BA,
  • Sleeps 14
#447255vb
    Year Round Waterfront Estate / Family Reunions - Sleeps 26
      7 Bedrooms,
    • 6 Bathrooms
    • 1 Half Bath
    • , Sleeps 26
    • 7 BR,
    • 6 BA,
    • 1 HF BA,
    • Sleeps 26
    #409548vb
      (4)
      Premium Waterfront Estate Property - $7,500/Week -
        5 Bedrooms,
      • 7 Bathrooms
      • , Sleeps 10
      • 5 BR,
      • 7 BA,
      • Sleeps 10
      #388823
        (8)
        Luxury home with pool and deep water dock.
          4 Bedrooms,
        • 4 Bathrooms
        • , Sleeps 8
        • 4 BR,
        • 4 BA,
        • Sleeps 8
        #336403
          (4)
          New listing with rural country charm, pool, and a deep water dock
            3 Bedrooms,
          • 2 Bathrooms
          • 1 Half Bath
          • , Sleeps 10
          2 night Minimum Stay
          • 3 BR,
          • 2 BA,
          • 1 HF BA,
          • Sleeps 10
          #3021814
            (5)
            Luxurious and Extremely Private Waterfront Estate
              9 Bedrooms,
            • 7 Bathrooms
            • 2 Half Baths
            • , Sleeps 20
            2 night Minimum Stay
            • 9 BR,
            • 7 BA,
            • 2 HF BA,
            • Sleeps 20
            #942769
              (5)
              Magnificent Vacation Rental home - 'Compass Rose' with pool and dock
                5 Bedrooms,
              • 2 Bathrooms
              • 1 Half Bath
              • , Sleeps 8
              7 night Minimum Stay
              • 5 BR,
              • 2 BA,
              • 1 HF BA,
              • Sleeps 8
              #234152
                St. Michaels Premier Waterfront estate close to town, golfcourse, Harbor,Museum
                  6 Bedrooms,
                • 5 Bathrooms
                • 1 Half Bath
                • , Sleeps 12
                • 6 BR,
                • 5 BA,
                • 1 HF BA,
                • Sleeps 12
                #113980
                  Beautiful and Very Private Historic Waterfront Estate House
                    6 Bedrooms,
                  • 5 Bathrooms
                  • 1 Half Bath
                  • , Sleeps 12
                  • 6 BR,
                  • 5 BA,
                  • 1 HF BA,
                  • Sleeps 12
                  #965364
                    (5)
                    Waterfront vacation on a private, historic estate
                      5 Bedrooms,
                    • 3 Bathrooms
                    • 1 Half Bath
                    • , Sleeps 12
                    • 5 BR,
                    • 3 BA,
                    • 1 HF BA,
                    • Sleeps 12
                    #297871
                      Eastern Shore Waterfront Estate, Private Beach, Deep Water
                        8 Bedrooms,
                      • 6 Bathrooms
                      • 1 Half Bath
                      • , Sleeps 15
                      • 8 BR,
                      • 6 BA,
                      • 1 HF BA,
                      • Sleeps 15
                      #211778
                        Willows on the Miles - Private, waterfront farmhouse estate- Miles River
                          5 Bedrooms,
                        • 3 Bathrooms
                        • , Sleeps 12
                        • 5 BR,
                        • 3 BA,
                        • Sleeps 12
                        #966959
                          2 Reviews
                          Longview -- Waterfront Estate w/ Pool & 3+ Acres
                            5 Bedrooms,
                          • 3 Bathrooms
                          • , Sleeps 10
                          • 5 BR,
                          • 3 BA,
                          • Sleeps 10
                          #109333
                            (3)
                            Relaxing New Waterfront Retreat W/ Private Pier, Pool & Kayaks
                              4 Bedrooms,
                            • 3 Bathrooms
                            • 1 Half Bath
                            • , Sleeps 11
                            Book it Now!
                            2 - 7 night Minimum Stay
                            • 4 BR,
                            • 3 BA,
                            • 1 HF BA,
                            • Sleeps 11
                            #347588vb
                              (24)
                              Island Estate - On Historic Potomac River - 600' Private Beach
                                6 Bedrooms,
                              • 4 Bathrooms
                              • 2 Half Baths
                              • , Sleeps 17
                              Book it Now!
                              7 night Minimum Stay
                              • 6 BR,
                              • 4 BA,
                              • 2 HF BA,
                              • Sleeps 17
                              #470492vb
                                Waterfront Country Estate Featured in Chesapeake Life Magazine
                                  10 Bedrooms,
                                • 1 Half Bath
                                • , Sleeps 26
                                7 night Minimum Stay
                                • 10 BR,
                                • 1 HF BA,
                                • Sleeps 26
                                #13516vb
                                  (3)
                                  Brittland Manor
                                    11 Bedrooms,
                                  • 8 Bathrooms
                                  • 1 Half Bath
                                  • , Sleeps 26
                                  • 11 BR,
                                  • 8 BA,
                                  • 1 HF BA,
                                  • Sleeps 26
                                  #223074vb
                                    Amazing Waterfront Estate Mins from Annapolis & St Michaels
                                      5 Bedrooms,
                                    • 5 Bathrooms
                                    • , Sleeps 16
                                    • 5 BR,
                                    • 5 BA,
                                    • Sleeps 16
                                    #383074vb
                                      (3)
                                      Exclusive Chesapeake Bay 250-Acre Estate - Beach,Pool,Dock
                                        11 Bedrooms,
                                      • 7 Bathrooms
                                      • 1 Half Bath
                                      • , Sleeps 34
                                      • 11 BR,
                                      • 7 BA,
                                      • 1 HF BA,
                                      • Sleeps 34
                                      #15537vb
                                        Beautiful, Quiet, Waterfront Home Close to St. Michaels/Easton
                                          5 Bedrooms, Sleeps 13
                                        • 5 BR,
                                        • Sleeps 13
                                        #304091vb
                                          2 Reviews
                                          2 Acres Waterfront Estate 20 Minutes from Annapolis/U~S~N~A~
                                            4 Bedrooms, Sleeps 10
                                          • 4 BR,
                                          • Sleeps 10
                                          #302733vb
                                            1 Review
                                            Escape to Kent Fields Farm a Country Estate for All Seasons.
                                              4 Bedrooms, Sleeps 12
                                            • 4 BR,
                                            • Sleeps 12
                                            #355727vb