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Chesapeake Bay Cottage Rentals(20)

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Pool, hot tub, big water views--what more could you ask for in a cottage
    3 Bedrooms,
  • 3 Bathrooms
    • , Sleeps 7
$508 - $712
per night

Pool, hot tub, big water views--what more could you ask for in a cottage

2 - 7 night Minimum Stay
  • 3 BR,
  • 3 BA,
  • Sleeps 7
  1. Chesapeake Bay >
  2. Tilghman Island Cottage
#204687vb
    (38)
    1920's Restored Waterman's Cottage with Fantastic Views!
      2 Bedrooms,
    • 1 Bathroom, 
    • 1 Half Bath
      • , Sleeps 4
    $392 - $450
    per night

    1920's Restored Waterman's Cottage with Fantastic Views!

    2 - 3 night Minimum Stay
    • 2 BR,
    • 1 BA,
    • 1 HF BA,
    • Sleeps 4
    1. Chesapeake Bay >
    2. Tilghman Island Cottage
    #922752
      (51)
      Thistle Dew - Will Do!! Waterfront, Pool, Decor, Location
        4 Bedrooms,
      • 3 Bathrooms
        • , Sleeps 8
      $535 - $685
      per night

      Thistle Dew - Will Do!! Waterfront, Pool, Decor, Location

      3 - 7 night Minimum Stay
      • 4 BR,
      • 3 BA,
      • Sleeps 8
      1. Chesapeake Bay >
      2. St. Michaels Cottage
      #449007vb
        (8)
        Private Cottage just outside St. Michaels with kayak and bikes included!
          3 Bedrooms,
        • 3 Bathrooms
          • , Sleeps 6
        $490 - $760
        per night

        Private Cottage just outside St. Michaels with kayak and bikes included!

        2 - 3 night Minimum Stay
        • 3 BR,
        • 3 BA,
        • Sleeps 6
        1. Chesapeake Bay >
        2. St. Michaels Cottage
        #389515vb
          (11)
          Waterfront getaway cottage near St. Michaels, hot tub, kayaks
            3 Bedrooms,
          • 2 Bathrooms
            • , Sleeps 6
          $400 - $550
          per night

          Waterfront getaway cottage near St. Michaels, hot tub, kayaks

          2 - 7 night Minimum Stay
          • 3 BR,
          • 2 BA,
          • Sleeps 6
          1. Chesapeake Bay >
          2. St. Michaels Cottage
          #448997vb
            (24)
            1940's Sears Cottage in Village
              2 Bedrooms,
            • 1 Bathroom
              • , Sleeps 4
            $307 - $360
            per night

            1940's Sears Cottage in Village

            2 - 3 night Minimum Stay
            • 2 BR,
            • 1 BA,
            • Sleeps 4
            1. Chesapeake Bay >
            2. Oxford Cottage
            #215987vb
              (59)
              Adorable cottage in heart of Oxford, walk to park, great family spot
                3 Bedrooms,
              • 2 Bathrooms
                • , Sleeps 6
              $452 - $552
              per night

              Adorable cottage in heart of Oxford, walk to park, great family spot

              2 - 3 night Minimum Stay
              • 3 BR,
              • 2 BA,
              • Sleeps 6
              1. Chesapeake Bay >
              2. Oxford Cottage
              #327397vb
                (14)
                3 Free Kayaks To Explore the Bay Included
                  4 Bedrooms,
                • 3 Bathrooms
                  • , Sleeps 8
                $458 - $562
                per night

                3 Free Kayaks To Explore the Bay Included

                2 - 7 night Minimum Stay
                • 4 BR,
                • 3 BA,
                • Sleeps 8
                1. Chesapeake Bay >
                2. Cambridge Cottage
                #348378
                  (6)
                  Private Cottage just outside St. Michaels with kayak and bikes included!
                    3 Bedrooms,
                  • 3 Bathrooms
                    • , Sleeps 6
                  $490 - $760
                  per night

                  Private Cottage just outside St. Michaels with kayak and bikes included!

                  2 - 3 night Minimum Stay
                  • 3 BR,
                  • 3 BA,
                  • Sleeps 6
                  1. Chesapeake Bay >
                  2. St. Michaels Cottage
                  #960147
                    (11)
                    Memory Lane Delivers Great Oxford Location and Fabulous Decorating
                      4 Bedrooms,
                    • 2 Bathrooms, 
                    • 1 Half Bath
                      • , Sleeps 8
                    $440 - $510
                    per night

                    Memory Lane Delivers Great Oxford Location and Fabulous Decorating

                    2 - 7 night Minimum Stay
                    • 4 BR,
                    • 2 BA,
                    • 1 HF BA,
                    • Sleeps 8
                    1. Chesapeake Bay >
                    2. Oxford Cottage
                    #390353vb
                      (5)
                      1900 Circa Duel Cottages Decorated to Die For
                        3 Bedrooms,
                      • 3 Bathrooms
                        • , Sleeps 6
                      $592 - $742
                      per night

                      1900 Circa Duel Cottages Decorated to Die For

                      2 - 7 night Minimum Stay
                      • 3 BR,
                      • 3 BA,
                      • Sleeps 6
                      1. Chesapeake Bay >
                      2. St. Michaels Cottage
                      #449015vb
                        (3)
                        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)
                          Historic, Renovated, Walking Distance to All Things Oxford
                            2 Bedrooms,
                          • 1 Bathroom, 
                          • 1 Half Bath
                            • , Sleeps 4
                          $282 - $422
                          per night

                          Historic, Renovated, Walking Distance to All Things Oxford

                          2 - 3 night Minimum Stay
                          • 2 BR,
                          • 1 BA,
                          • 1 HF BA,
                          • Sleeps 4
                          1. Chesapeake Bay >
                          2. Oxford Cottage
                          #449004vb
                            (6)
                            Single family vacation cottage with pool, kayaks, play gym and dock
                              3 Bedrooms,
                            • 1 Bathroom, 
                            • 1 Half Bath
                              • , Sleeps 6
                            $518 - $678
                            per night

                            Single family vacation cottage with pool, kayaks, play gym and dock

                            2 - 7 night Minimum Stay
                            • 3 BR,
                            • 1 BA,
                            • 1 HF BA,
                            • Sleeps 6
                            1. Chesapeake Bay >
                            2. St. Michaels Cottage
                            #214581vb
                              (28)
                              Fabulous Private 29 Acres and 2,000' Shoreline Yet You Can Bike to Village
                                3 Bedrooms,
                              • 2 Bathrooms
                                • , Sleeps 6
                              $365 - $422
                              per night

                              Fabulous Private 29 Acres and 2,000' Shoreline Yet You Can Bike to Village

                              2 - 3 night Minimum Stay
                              • 3 BR,
                              • 2 BA,
                              • Sleeps 6
                              1. Chesapeake Bay >
                              2. Oxford Cottage
                              #449001vb
                                (9)
                                HERON'S REST GUEST COTTAGE - Military Discounts
                                  1 Bedrooms,
                                • 1 Bathroom
                                  • , Sleeps 4
                                $433
                                per night

                                HERON'S REST GUEST COTTAGE - Military Discounts

                                2 night Minimum Stay
                                • 1 BR,
                                • 1 BA,
                                • Sleeps 4
                                1. Chesapeake Bay >
                                2. North Beach Cottage
                                #285640
                                  (14)
                                  4 More choices from HomeAway International Websites
                                  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
                                      Magnificent Waterfront Cottage on 5 Acres with Private Beach and Dock
                                        3 Bedrooms,
                                      • 2 Bathrooms
                                        • , Sleeps 6

                                      Magnificent Waterfront Cottage on 5 Acres with Private Beach and Dock

                                      • 3 BR,
                                      • 2 BA,
                                      • Sleeps 6
                                      1. Chesapeake Bay >
                                      2. Kent Island Cottage
                                      #409507vb
                                        (8)
                                        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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