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14 houses

(5) Excellent 

Certificate of Excellence

    28

    Cozy & Spacious Chestertown Home

    Maryland / Chestertown

    Chestertown house

    4 8 2 nights min

    • 4 bedrooms
    • sleeps 8
    • 2 nights min
    • Nearest beach 8 mi
    • Swimming pool
    • Child Friendly

    Certificate of Excellence

    Price per night from

    $287

    Responds fast!
    avg. 1 hour 57 minutes

    Price per night from

    $287

    (3) Excellent 

      17

      Belle Rose Cottage at Victory Farm (Pet Friendly!)

      Maryland / Chestertown

      Chestertown house

      1 3 1 night min

      • 1 bedroom
      • sleeps 3
      • 1 night min
      • Child Friendly
      • Air conditioning
      • Pet Friendly

      Price per night from

      $154

      Price per night from

      $154

      (4) Very Good 

        11

        Chester River House with Views

        Maryland / Chestertown

        Chestertown house

        3 7 2 nights min

        • 3 bedrooms
        • sleeps 7
        • 2 nights min
        • Child Friendly

        Price per night from

        $178

        Responds fast!
        avg. 3 hours 8 minutes

        Price per night from

        $178

        (3) Very Good 

          14

          Retreat at a quiet, water front cottage

          Maryland / Chestertown

          Chestertown house

          3 8 2 nights min

          • 3 bedrooms
          • sleeps 8
          • 2 nights min
          • Child Friendly
          • Air conditioning
          • Private garden
          “Blissful, Expansive water views with awesome sunsets!” This rental has everything you could possibly need. A public boat launch a 1/4 mile or less from the house. Kayaks and a large amount of water to explore. A gorgeous 10 mile drive or bike ride fro

          Price per night from

          $338

          Price per night from

          $338

          (2) Very Good 

            16

            Gorgeous Home on Chester River

            Maryland / Chestertown

            Chestertown house

            4 8 2 nights min

            • 4 bedrooms
            • sleeps 8
            • 2 nights min
            • Beach / lakeside relaxation
            • Child Friendly
            • Air conditioning

            Price per night from

            $745

            Price per night from

            $745

            (1) Excellent 

              22

              Sunview Cottage on Chesapeake Bay

              Maryland / Chestertown

              Chestertown house

              2 5 3 nights min

              • 2 bedrooms
              • sleeps 5
              • 3 nights min
              • Beach / lakeside relaxation
              • Child Friendly
              • Air conditioning

              Price per night from

              $165

              Price per night from

              $165

              Great rentals within 20 miles that match your search

              Distance approx 10.97 km from Chestertown Show on Map

                8

                Bay Cottage

                Maryland / Rock Hall

                Rock Hall house

                2 5 2 nights min

                • 2 bedrooms
                • sleeps 5
                • 2 nights min
                • Child Friendly
                • Air conditioning
                • Pet Friendly

                Price per night from

                $227

                Responds fast!
                avg. 3 hours 15 minutes

                Price per night from

                $227

                Distance approx 11.02 km from Chestertown Show on Map

                  12

                  Bayside Retreat

                  Maryland / Rock Hall

                  Rock Hall house

                  3 6 min stay varies

                  • 3 bedrooms
                  • sleeps 6
                  • min stay varies
                  • Child Friendly
                  • Air conditioning
                  • Pet Friendly

                  Price per night from

                  $142

                  Responds fast!
                  avg. 3 hours 15 minutes

                  Price per night from

                  $142

                  Distance approx 10.9 km from Chestertown Show on Map

                    9

                    Summer House in Rock Hall

                    Maryland / Rock Hall

                    Rock Hall house

                    3 8 min stay varies

                    • 3 bedrooms
                    • sleeps 8
                    • min stay varies
                    • Child Friendly
                    • Car not necessary
                    • Air conditioning

                    Price per night from

                    $285

                    Responds fast!
                    avg. 3 hours 15 minutes

                    Price per night from

                    $285

                    Distance approx 8.78 km from Chestertown Show on Map

                      43

                      Skeet shoot in the back yard of your rental

                      Maryland / Rock Hall

                      Rock Hall house

                      3 9 1 night min

                      • 3 bedrooms
                      • sleeps 9
                      • 1 night min
                      • Child Friendly

                      Price per night from

                      $182

                      Price per night from

                      $182

                      Distance approx 10.7 km from Chestertown Show on Map

                      (3) Excellent 

                        12

                        Sailors Crossing

                        Maryland / Rock Hall

                        Rock Hall house

                        3 10 2 nights min

                        • 3 bedrooms
                        • sleeps 10
                        • 2 nights min
                        • Child Friendly
                        • Pet Friendly

                        Price per night from

                        $387

                        Responds fast!
                        avg. 3 hours 15 minutes

                        Price per night from

                        $387

                        Distance approx 18.6 km from Chestertown

                          26

                          Love Point Luxury Waterfront in Stevensville

                          Kent Island / Stevensville

                          Stevensville house

                          3 10 3 nights min

                          • 3 bedrooms
                          • sleeps 10
                          • 3 nights min
                          • Beach / lakeside relaxation
                          • Child Friendly
                          • Air conditioning

                          Price per night from

                          $1,591

                          Price per night from

                          $1,591

                          Distance approx 7.52 km from Chestertown

                          (2) Very Good 

                            39

                            Big BD in Civil War House starting at 55$/night

                            Maryland / Still Pond

                            Still Pond house

                            1 3 1 night min

                            • 1 bedroom
                            • sleeps 3
                            • 1 night min
                            • Nearest beach 5 mi
                            • Child Friendly
                            • Air conditioning
                            “One night in Still Pond” Pleasant stay with an entrance of beautiful blooming flowers. The hostess welcomed us and informed us of the essentials such as lights, cooling and bathroom, etc.

                            Price per night from

                            $63

                            Price per night from

                            $63

                            Distance approx 7.52 km from Chestertown

                              58

                              Great BD in Civil War House starting at 55$/night

                              Maryland / Still Pond

                              Still Pond house

                              2 6 1 night min

                              • 2 bedrooms
                              • sleeps 6
                              • 1 night min
                              • Nearest beach 5 mi
                              • Child Friendly
                              • Air conditioning

                              Price per night from

                              $86

                              Price per night from

                              $86