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Chesapeake Bay Cottage Rentals Pet Friendly(37)

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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
$583 - $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 - $500
    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 - $752
      per night

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

      2 - 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 - $610
        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
          $425 - $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
            (25)
            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
              $502 - $552
              per night

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

              2 night Minimum Stay
              • 3 BR,
              • 2 BA,
              • Sleeps 6
              1. Chesapeake Bay >
              2. Oxford Cottage
              #327397vb
                (14)
                Private Cottage just outside St. Michaels with kayak and bikes included!
                  3 Bedrooms,
                • 3 Bathrooms
                  • , Sleeps 6
                $490 - $610
                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 - $535
                  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 - $768
                    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)
                      Waterfront Tilghman Island Cottage
                        2 Bedrooms,
                      • 1 Bathroom
                        • , Sleeps 6
                      $75 - $175
                      per night

                      Waterfront Tilghman Island Cottage

                      Book it Now!
                      2 night Minimum Stay
                      • 2 BR,
                      • 1 BA,
                      • Sleeps 6
                      1. Chesapeake Bay >
                      2. Tilghman Island Cottage
                      #244823vb
                        2 Reviews
                        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
                          $348 - $422
                          per night

                          Historic, Renovated, Walking Distance to All Things Oxford

                          2 night Minimum Stay
                          • 2 BR,
                          • 1 BA,
                          • 1 HF BA,
                          • Sleeps 4
                          1. Chesapeake Bay >
                          2. Oxford Cottage
                          #449004vb
                            (6)
                            Tilghman Island Cottage for Six
                              3 Bedrooms,
                            • 2 Bathrooms
                              • , Sleeps 6
                            $850
                            per week

                            Tilghman Island Cottage for Six

                            7 night Minimum Stay
                            • 3 BR,
                            • 2 BA,
                            • Sleeps 6
                            1. Chesapeake Bay >
                            2. Tilghman Island Cottage
                            #383239
                              (19)
                              Luxury Waterfront in Cambridge with Pool, Hot Tub, Dock!
                                3 Bedrooms, Sleeps 8
                              $379 - $459
                              per night

                              Luxury Waterfront in Cambridge with Pool, Hot Tub, Dock!

                              3 night Minimum Stay
                              • 3 BR,
                              • Sleeps 8
                              1. Chesapeake Bay >
                              2. Cambridge Cottage
                              #277043
                                (11)
                                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)
                                    Single family vacation cottage with pool, kayaks, play gym and dock
                                      3 Bedrooms,
                                    • 1 Bathroom, 
                                    • 1 Half Bath
                                      • , Sleeps 6
                                    $548 - $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)
                                      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)
                                        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)
                                          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)
                                            The True 'Bay Life'
                                              3 Bedrooms,
                                            • 1 Bathroom
                                              • , Sleeps 6
                                            $175 - $225
                                            per night

                                            The True 'Bay Life'

                                            2 night Minimum Stay
                                            • 3 BR,
                                            • 1 BA,
                                            • Sleeps 6
                                            1. Chesapeake Bay >
                                            2. Deale Cottage
                                            #3010364
                                              2 Reviews
                                              15 More choices from HomeAway International Websites
                                              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)
                                                Cottage with Art Studio, Near Beach, Dog-Friendly
                                                  1 Bedrooms,
                                                • 1 Bathroom
                                                  • , Sleeps 5
                                                $125 - $195
                                                per night

                                                Cottage with Art Studio, Near Beach, Dog-Friendly

                                                Book it Now!
                                                2 night Minimum Stay
                                                • 1 BR,
                                                • 1 BA,
                                                • Sleeps 5
                                                1. Chesapeake Bay >
                                                2. North Beach Cottage
                                                #371261vb
                                                  (4)
                                                  WATERFRONT 3 BR cute country cottage.deep water,dock, 2 mi from town
                                                    3 Bedrooms,
                                                  • 1 Bathroom
                                                    • , Sleeps 6
                                                  $200 - $250
                                                  per night

                                                  WATERFRONT 3 BR cute country cottage.deep water,dock, 2 mi from town

                                                  2 night Minimum Stay
                                                  • 3 BR,
                                                  • 1 BA,
                                                  • Sleeps 6
                                                  1. Chesapeake Bay >
                                                  2. Chestertown Cottage
                                                  #418738vb
                                                    (7)
                                                    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
                                                      Awesome Sunrises on the Chesapeake Bay!
                                                        1 Bedrooms, Sleeps 4
                                                      $125
                                                      per night

                                                      Awesome Sunrises on the Chesapeake Bay!

                                                      2 night Minimum Stay
                                                      • 1 BR,
                                                      • Sleeps 4
                                                      1. Chesapeake Bay >
                                                      2. Deale Cottage
                                                      #364413vb
                                                        (8)
                                                        Best St. Michaels Cottage in Best Location Walk to Everything
                                                          2 Bedrooms, Sleeps 5

                                                        Best St. Michaels Cottage in Best Location Walk to Everything

                                                        • 2 BR,
                                                        • Sleeps 5
                                                        1. Chesapeake Bay >
                                                        2. St. Michaels Cottage
                                                        #229963vb
                                                          (12)
                                                          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)
                                                            6.5 Acre Waterfront Family Retreat with Pool and Sandy Beach!
                                                              3 Bedrooms,
                                                            • 2 Bathrooms
                                                              • , Sleeps 9

                                                            6.5 Acre Waterfront Family Retreat with Pool and Sandy Beach!

                                                            • 3 BR,
                                                            • 2 BA,
                                                            • Sleeps 9
                                                            1. Chesapeake Bay >
                                                            2. Cambridge Cottage
                                                            #411385vb
                                                              (5)
                                                              • 1 - 30 of 37
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