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Chesapeake Bay Beach Cottage Rentals(21)

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Darling in town cottage with private sandy beach and dock
    3 Bedrooms,
  • 2 Bathrooms
    • , Sleeps 6
$398 - $472
per night

Darling in town cottage with private sandy beach and dock

2 - 7 night Minimum Stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
  1. Chesapeake Bay >
  2. Oxford Cottage
#327383vb
    (31)
    Sea Glass Cottage on the Bay - St Michaels MD Area
      3 Bedrooms,
    • 1 Bathroom, 
    • 1 Half Bath
      • , Sleeps 6
    $300 - $400
    per night

    Sea Glass Cottage on the Bay - St Michaels MD Area

    2 night Minimum Stay
    • 3 BR,
    • 1 BA,
    • 1 HF BA,
    • Sleeps 6
    1. Chesapeake Bay >
    2. St. Michaels Cottage
    #3014081
      (4)
      Vintage Waterfront Cottage with Fishing Pier on the Chesapeake Bay.
        2 Bedrooms,
      • 1 Bathroom
        • , Sleeps 5

      Vintage Waterfront Cottage with Fishing Pier on the Chesapeake Bay.

      • 2 BR,
      • 1 BA,
      • Sleeps 5
      1. Chesapeake Bay >
      2. Deal Island Cottage
      #385730
        (11)
        Renovated cottage with Chesapeake Bay sandy beach direct access
          1 Bedrooms,
        • 1 Bathroom
          • , Sleeps 3
        $90 - $150
        per night

        Renovated cottage with Chesapeake Bay sandy beach direct access

        Book it Now!
        2 night Minimum Stay
        • 1 BR,
        • 1 BA,
        • Sleeps 3
        1. Chesapeake Bay >
        2. Point Lookout Cottage
        #908053
          (10)
          Harbor Cottage at the Chesapeake Bay Vacation Rental
            2 Bedrooms,
          • 2 Bathrooms
            • , Sleeps 6
          $185 - $260
          per night

          Harbor Cottage at the Chesapeake Bay Vacation Rental

          3 night Minimum Stay
          • 2 BR,
          • 2 BA,
          • Sleeps 6
          1. Chesapeake Bay >
          2. St. Leonard Cottage
          #122453
            (17)
            St. Michael's premier in town summer vacation cottage!
              2 Bedrooms,
            • 2 Bathrooms
              • , Sleeps 4

            St. Michael's premier in town summer vacation cottage!

            • 2 BR,
            • 2 BA,
            • Sleeps 4
            1. Chesapeake Bay >
            2. St. Michaels Cottage
            #287681
              (26)
              HERON'S REST GUEST COTTAGE - Your Paradise on the Bay!!
                1 Bedrooms,
              • 1 Bathroom
                • , Sleeps 4
              $433
              per night

              HERON'S REST GUEST COTTAGE - Your Paradise on the Bay!!

              2 night Minimum Stay
              • 1 BR,
              • 1 BA,
              • Sleeps 4
              1. Chesapeake Bay >
              2. North Beach Cottage
              #285640
                (14)
                Waterfront Chesapeake Bay Retreat.
                  3 Bedrooms,
                • 1 Bathroom
                  • , Sleeps 6

                Waterfront Chesapeake Bay Retreat.

                • 3 BR,
                • 1 BA,
                • Sleeps 6
                1. Chesapeake Bay >
                2. Tyaskin Cottage
                #371260
                  (11)
                  Chesapeake Bay fossil hunting from your own front yard! 50 min. D.C
                    3 Bedrooms,
                  • 1 Bathroom
                    • , Sleeps 6

                  Chesapeake Bay fossil hunting from your own front yard! 50 min. D.C

                  • 3 BR,
                  • 1 BA,
                  • Sleeps 6
                  1. Chesapeake Bay >
                  2. St. Leonard Cottage
                  #138139
                    (4)
                    Ber Na Mara: Chesapeake Beach House with Panoramic Bay Views.
                      3 Bedrooms, Sleeps 8
                    $200 - $325
                    per night

                    Ber Na Mara: Chesapeake Beach House with Panoramic Bay Views.

                    Book it Now!
                    2 - 7 night Minimum Stay
                    • 3 BR,
                    • Sleeps 8
                    1. Chesapeake Bay >
                    2. Point Lookout Cottage
                    #437322vb
                      (7)
                      Waterfront Carriage House - Estate Setting - Couple's Delight
                        1 Bedrooms, Sleeps 2
                      $125 - $225
                      per night

                      Waterfront Carriage House - Estate Setting - Couple's Delight

                      2 night Minimum Stay
                      • 1 BR,
                      • Sleeps 2
                      1. Chesapeake Bay >
                      2. Cambridge Cottage
                      #61400vb
                        (16)
                        Classic Chesapeake Bay Cottage: Gorgeous views + beach
                          1 Bedrooms,
                        • 1 Bathroom
                          • , Sleeps 3
                        $110 - $120
                        per night

                        Classic Chesapeake Bay Cottage: Gorgeous views + beach

                        Book it Now!
                        2 night Minimum Stay
                        • 1 BR,
                        • 1 BA,
                        • Sleeps 3
                        1. Chesapeake Bay >
                        2. Point Lookout Cottage
                        #470232vb
                          Cove Point Lighthouse - Both sides of the Keeper's Cottage Duplex
                            6 Bedrooms,
                          • 4 Bathrooms, 
                          • 2 Half Baths
                            • , Sleeps 16
                          $350 - $575
                          per night

                          Cove Point Lighthouse - Both sides of the Keeper's Cottage Duplex

                          3 night Minimum Stay
                          • 6 BR,
                          • 4 BA,
                          • 2 HF BA,
                          • Sleeps 16
                          1. Chesapeake Bay >
                          2. Solomons Island Cottage
                          #436958vb
                            2 Reviews
                            Cove Point Lighthouse - One side of the Keeper's Cottage Duplex
                              3 Bedrooms,
                            • 2 Bathrooms, 
                            • 1 Half Bath
                              • , Sleeps 8
                            $184 - $400
                            per night

                            Cove Point Lighthouse - One side of the Keeper's Cottage Duplex

                            3 night Minimum Stay
                            • 3 BR,
                            • 2 BA,
                            • 1 HF BA,
                            • Sleeps 8
                            1. Chesapeake Bay >
                            2. Solomons Island Cottage
                            #469385vb
                              Cottage and or House on estate in Cambridge, MD
                                1 Bedrooms,
                              • 1 Bathroom, 
                              • 1 Half Bath
                                • , Sleeps 4

                              Cottage and or House on estate in Cambridge, MD

                              • 1 BR,
                              • 1 BA,
                              • 1 HF BA,
                              • Sleeps 4
                              1. Chesapeake Bay >
                              2. Cambridge Cottage
                              #429271vb
                                (7)
                                Skipjack Cottage - on the Chesapeake Bay...Come Relax
                                  2 Bedrooms, Sleeps 6
                                $175
                                per night

                                Skipjack Cottage - on the Chesapeake Bay...Come Relax

                                2 night Minimum Stay
                                • 2 BR,
                                • Sleeps 6
                                1. Chesapeake Bay >
                                2. North Beach Cottage
                                #368160vb
                                  (3)
                                  Beachfront cottages
                                    2 Bedrooms,
                                  • 1 Bathroom
                                    • , Sleeps 8

                                  Beachfront cottages

                                  • 2 BR,
                                  • 1 BA,
                                  • Sleeps 8
                                  1. Chesapeake Bay >
                                  2. Betterton Cottage
                                  #470915vb
                                    Vintage Beach Cottage
                                      2 Bedrooms,
                                    • 1 Bathroom
                                      • , Sleeps 6
                                    $300
                                    per night

                                    Vintage Beach Cottage

                                    2 night Minimum Stay
                                    • 2 BR,
                                    • 1 BA,
                                    • Sleeps 6
                                    1. Chesapeake Bay >
                                    2. Point Lookout Cottage
                                    #347568vb
                                      (3)
                                      Cozy Waterfront Cottage-
                                        3 Bedrooms, Sleeps 8

                                      Cozy Waterfront Cottage-

                                      • 3 BR,
                                      • Sleeps 8
                                      1. Chesapeake Bay >
                                      2. Tyaskin Cottage
                                      #253476vb
                                        2 Reviews
                                        Chesapeake Bay Md, Cottage for Yearly Rental. 1hr from D.C.
                                          1 Bedrooms,
                                        • 1 Bathroom
                                          • , Sleeps 5

                                        Chesapeake Bay Md, Cottage for Yearly Rental. 1hr from D.C.

                                        • 1 BR,
                                        • 1 BA,
                                        • Sleeps 5
                                        1. Chesapeake Bay >
                                        2. Chesapeake Beach Cottage
                                        #363584vb
                                          1 Review
                                          Vacation Home Close to Dc. Chesapeake Bay View and Walk to the
                                            3 Bedrooms, Sleeps 6

                                          Vacation Home Close to Dc. Chesapeake Bay View and Walk to the

                                          • 3 BR,
                                          • Sleeps 6
                                          1. Chesapeake Bay >
                                          2. St. Leonard Cottage
                                          #391580vb
                                            1 Review
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