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Chesapeake Bay Cottage Rentals with Parking Included(43)

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Breezy Point Waterfront Cottage-Pool-Dock-Recreation Pavilion
    5 Bedrooms,
  • 3 Bathrooms
    • , Sleeps 6
$2,380 - $3,800
per week

Breezy Point Waterfront Cottage-Pool-Dock-Recreation Pavilion

7 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 6
  1. Chesapeake Bay >
  2. St. Michaels Cottage
#254824
    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
      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
        (5)
        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)
            Waterfront Country Cottage Close To St Michaels
              3 Bedrooms,
            • 3 Bathrooms
              • , Sleeps 6
            $280 - $495
            per night

            Waterfront Country Cottage Close To St Michaels

            2 night minimum stay
            • 3 BR,
            • 3 BA,
            • Sleeps 6
            1. Chesapeake Bay >
            2. St. Michaels Cottage
            #185818
              (10)
              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
                  (11)
                  Chester River Water Front Retreat - Sunrise and Sunset Views
                    3 Bedrooms, Sleeps 8
                  $300 - $350
                  per night

                  Chester River Water Front Retreat - Sunrise and Sunset Views

                  2 night minimum stay
                  • 3 BR,
                  • Sleeps 8
                  1. Chesapeake Bay >
                  2. Chestertown Cottage
                  #907492
                    (12)
                    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)
                      Chesapeake Bayfront Cottage - Port Republic, Calvert County, MD
                        2 Bedrooms,
                      • 1 Bathroom
                        • , Sleeps 6
                      $198 - $198
                      per night

                      Chesapeake Bayfront Cottage - Port Republic, Calvert County, MD

                      2 - 7 night minimum stay
                      • 2 BR,
                      • 1 BA,
                      • Sleeps 6
                      1. Chesapeake Bay >
                      2. Port Republic Cottage
                      #125200
                        Cozy waterfront cottage with hot tub, large screened porch and scenic views
                          3 Bedrooms,
                        • 1 Bathroom
                          • , Sleeps 5
                        $190 - $250
                        per night

                        Cozy waterfront cottage with hot tub, large screened porch and scenic views

                        5 night minimum stay
                        • 3 BR,
                        • 1 BA,
                        • Sleeps 5
                        1. Chesapeake Bay >
                        2. Cambridge Cottage
                        #277276
                          (23)
                          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
                            (27)
                            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
                              HERON'S REST GUEST COTTAGE - Your Slice of Paradise!!
                                1 Bedrooms,
                              • 1 Bathroom
                                • , Sleeps 4
                              $433
                              per night

                              HERON'S REST GUEST COTTAGE - Your Slice of Paradise!!

                              2 night minimum stay
                              • 1 BR,
                              • 1 BA,
                              • Sleeps 4
                              1. Chesapeake Bay >
                              2. North Beach Cottage
                              #285640
                                (14)
                                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)
                                  27 More choices from HomeAway International Websites
                                  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
                                    (17)
                                    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
                                      (8)
                                      The Relax-Inn Deal Island
                                        3 Bedrooms,
                                      • 1 Bathroom
                                        • , Sleeps 6
                                      $110
                                      per night

                                      The Relax-Inn Deal Island

                                      Book it Now!
                                      3 night minimum stay
                                      • 3 BR,
                                      • 1 BA,
                                      • Sleeps 6
                                      1. Chesapeake Bay >
                                      2. Deal Island Cottage
                                      #407081vb
                                        (6)
                                        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
                                          (5)
                                          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
                                            (8)
                                            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
                                              2 Reviews
                                              Quiet Beautiful Cottage. 2+ Br, 2 Full Bath On Bohemia River
                                                2 Bedrooms,
                                              • 2 Bathrooms
                                                • , Sleeps 6
                                              $200 - $275
                                              per night

                                              Quiet Beautiful Cottage. 2+ Br, 2 Full Bath On Bohemia River

                                              2 night minimum stay
                                              • 2 BR,
                                              • 2 BA,
                                              • Sleeps 6
                                              1. Chesapeake Bay >
                                              2. North East Cottage
                                              #403229vb
                                                1 Review
                                                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
                                                  (4)
                                                  Beachfront cottages
                                                    2 Bedrooms,
                                                  • 1 Bathroom
                                                    • , Sleeps 8
                                                  $700
                                                  per week

                                                  Beachfront cottages

                                                  7 night minimum stay
                                                  • 2 BR,
                                                  • 1 BA,
                                                  • Sleeps 8
                                                  1. Chesapeake Bay >
                                                  2. Betterton Cottage
                                                  #470915vb
                                                    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)
                                                      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
                                                        (9)
                                                        Hard Head Cottage - Sleeps 4/Near Dogwood Harbor & Boat Ramp
                                                          2 Bedrooms,
                                                        • 1 Bathroom
                                                          • , Sleeps 4

                                                        Hard Head Cottage - Sleeps 4/Near Dogwood Harbor & Boat Ramp

                                                        • 2 BR,
                                                        • 1 BA,
                                                        • Sleeps 4
                                                        1. Chesapeake Bay >
                                                        2. Tilghman Island Cottage
                                                        #404469vb
                                                          (4)
                                                          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)
                                                            Walk To Everything! Located In Heart Of St. Michaels
                                                              1 Bedrooms,
                                                            • 1 Bathroom
                                                              • , Sleeps 3
                                                            $250
                                                            per night

                                                            Walk To Everything! Located In Heart Of St. Michaels

                                                            2 night minimum stay
                                                            • 1 BR,
                                                            • 1 BA,
                                                            • Sleeps 3
                                                            1. Chesapeake Bay >
                                                            2. St. Michaels Cottage
                                                            #481455vb
                                                              • 1 - 30 of 43
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