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  • Showing 1-37 of 37
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    Exceptional! 5.0/5
    (10 reviews)
    avg/night
    • 3 BR
    • 2 BA
    • Sleeps 6
    House #220506vb
    10
    Viewed 14 times in the last 48 hours
      Exceptional! 5.0/5
      (7 reviews)
      avg/night
      • 3 BR
      • 2 BA
      • Sleeps 6
      House #759063vb
      7
      Viewed 8 times in the last 48 hours
        avg/night
        • 3 BR
        • 1 BA
        • 1 HF BA
        • Sleeps 6
        House #4252597
        1
        Viewed 14 times in the last 48 hours
          Exceptional! 5.0/5
          (41 reviews)
          avg/night
          • 3 BR
          • 3 BA
          • Sleeps 8
          House #294688vb
          41
          Viewed 76 times in the last 48 hours
            Excellent! 4.7/5
            (15 reviews)
            avg/night
            • 4 BR
            • 2 BA
            • Sleeps 10
            House #704799vb
            15
            Viewed 57 times in the last 48 hours
              Wonderful! 4.8/5
              (13 reviews)
              avg/night
              • 4 BR
              • 3 BA
              • Sleeps 12
              House #3786046
              13
              Viewed 71 times in the last 48 hours
                • 2 BR
                • 1 BA
                • Sleeps 6
                House #707088vb
                1
                  Excellent! 4.6/5
                  (30 reviews)
                  avg/night
                  • 3 BR
                  • 2 BA
                  • Sleeps 12
                  House #7002752
                  30
                  Viewed 34 times in the last 48 hours
                    Exceptional! 5.0/5
                    (40 reviews)
                    avg/night
                    • 4 BR
                    • 4 BA
                    • 1 HF BA
                    • Sleeps 13
                    House #356548vb
                    40
                    Viewed 21 times in the last 48 hours
                      Wonderful! 4.9/5
                      (10 reviews)
                      avg/night
                      • 4 BR
                      • 2 BA
                      • Sleeps 10
                      House #398147vb
                      10
                      Viewed 25 times in the last 48 hours
                        avg/night
                        • 2 BR
                        • 1 BA
                        • Sleeps 5
                        House #4112420
                        1
                        Viewed 17 times in the last 48 hours
                          Wonderful! 4.8/5
                          (25 reviews)
                          avg/night
                          • 2 BR
                          • 1 BA
                          • 1 HF BA
                          • Sleeps 6
                          House #431733vb
                          25
                          Viewed 6 times in the last 48 hours
                            Excellent! 4.3/5
                            (9 reviews)
                            avg/night
                            • 3 BR
                            • 2 BA
                            • Sleeps 9
                            House #706116vb
                            9
                            Viewed 20 times in the last 48 hours
                              • 3 BR
                              • 2 BA
                              • 1 HF BA
                              • Sleeps 8
                              House #797359vb
                              3
                              Viewed 13 times in the last 48 hours
                                Excellent! 4.7/5
                                (13 reviews)
                                avg/night
                                • 6 BR
                                • 2 BA
                                • Sleeps 11
                                House #235930
                                13
                                Viewed 52 times in the last 48 hours
                                  Excellent! 4.7/5
                                  (29 reviews)
                                  avg/night
                                  • 3 BR
                                  • 1 BA
                                  • 1 HF BA
                                  • Sleeps 7
                                  House #429782vb
                                  29
                                  Viewed 42 times in the last 48 hours
                                    Wonderful! 4.9/5
                                    (10 reviews)
                                    avg/night
                                    • 3 BR
                                    • 1 BA
                                    • 1 HF BA
                                    • Sleeps 8
                                    House #571411vb
                                    10
                                    Viewed 9 times in the last 48 hours
                                      Very Good! 4.0/5
                                      (5 reviews)
                                      avg/night
                                      • 5 BR
                                      • 3 BA
                                      • Sleeps 8
                                      House #726629vb
                                      5
                                      Viewed 25 times in the last 48 hours
                                        Wonderful! 4.9/5
                                        (18 reviews)
                                        avg/night
                                        • 2 BR
                                        • 1 BA
                                        • Sleeps 6
                                        House #53282vb
                                        18
                                        Viewed 7 times in the last 48 hours
                                          Wonderful! 4.9/5
                                          (8 reviews)
                                          avg/night
                                          • 4 BR
                                          • 3 BA
                                          • 1 HF BA
                                          • Sleeps 8
                                          House #458295vb
                                          8
                                          Viewed 26 times in the last 48 hours
                                            • 3 BR
                                            • 2 BA
                                            • 1 HF BA
                                            • Sleeps 8
                                            House #565548vb
                                            3
                                            Viewed 8 times in the last 48 hours
                                              • 4 BR
                                              • 2 BA
                                              • Sleeps 8
                                              House #3917327
                                              Viewed 35 times in the last 48 hours
                                                avg/night
                                                • 4 BR
                                                • 2 BA
                                                • 1 HF BA
                                                • Sleeps 11
                                                House #592542vb
                                                Viewed 15 times in the last 48 hours
                                                  avg/night
                                                  • 3 BR
                                                  • 1 BA
                                                  • Sleeps 8
                                                  House #4204088
                                                  1
                                                  Viewed 16 times in the last 48 hours
                                                    Exceptional! 5.0/5
                                                    (9 reviews)
                                                    avg/night
                                                    • 2 BR
                                                    • 1 BA
                                                    • 1 HF BA
                                                    • Sleeps 4
                                                    House #473897vb
                                                    9
                                                    Viewed 7 times in the last 48 hours
                                                      avg/night
                                                      • 5 BR
                                                      • 5 BA
                                                      • 1 HF BA
                                                      • Sleeps 10
                                                      House #600779vb
                                                      3
                                                      Viewed 21 times in the last 48 hours
                                                        avg/night
                                                        • 3 BR
                                                        • 1 BA
                                                        • Sleeps 8
                                                        House #440251vb
                                                        1
                                                        Viewed 21 times in the last 48 hours
                                                          avg/night
                                                          • 5 BR
                                                          • 4 BA
                                                          • Sleeps 11
                                                          House #912542vb
                                                          Viewed 7 times in the last 48 hours
                                                            • 4 BR
                                                            • 4 BA
                                                            • Sleeps 10
                                                            House #732410vb
                                                            Viewed 8 times in the last 48 hours
                                                              avg/night
                                                              • 4 BR
                                                              • 4 BA
                                                              • Sleeps 8
                                                              House #4176971
                                                              Viewed 10 times in the last 48 hours
                                                                avg/night
                                                                • 7 BR
                                                                • 4 BA
                                                                • 1 HF BA
                                                                • Sleeps 13
                                                                House #935769vb
                                                                4
                                                                Viewed 30 times in the last 48 hours
                                                                  Wonderful! 4.8/5
                                                                  (19 reviews)
                                                                  avg/night
                                                                  • 4 BR
                                                                  • 2 BA
                                                                  • Sleeps 12
                                                                  House #395841vb
                                                                  19
                                                                  Viewed 51 times in the last 48 hours
                                                                    Wonderful! 4.9/5
                                                                    (27 reviews)
                                                                    avg/night
                                                                    • 4 BR
                                                                    • 4 BA
                                                                    • Sleeps 8
                                                                    House #410328vb
                                                                    27
                                                                    Viewed 26 times in the last 48 hours
                                                                      avg/night
                                                                      • 5 BR
                                                                      • 3 BA
                                                                      • 1 HF BA
                                                                      • Sleeps 15
                                                                      House #124956vb
                                                                      1
                                                                      Viewed 9 times in the last 48 hours
                                                                        Exceptional! 5.0/5
                                                                        (9 reviews)
                                                                        avg/night
                                                                        • 6 BR
                                                                        • 4 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 11
                                                                        House #734393vb
                                                                        9
                                                                        Viewed 25 times in the last 48 hours
                                                                          • 4 BR
                                                                          • 2 BA
                                                                          • 1 HF BA
                                                                          • Sleeps 9
                                                                          House #213261vb
                                                                            Exceptional! 5.0/5
                                                                            (10 reviews)
                                                                            avg/night
                                                                            • 5 BR
                                                                            • 3 BA
                                                                            • 1 HF BA
                                                                            • Sleeps 20
                                                                            House #571534vb
                                                                            10
                                                                            Viewed 13 times in the last 48 hours
                                                                            • 1 - 37 of 37

                                                                            Chestertown: House Rentals (37)

                                                                             

                                                                            Recent Chestertown Reviews

                                                                            We love this place.

                                                                            5 of 5
                                                                            We've stayed at this location for two summer vacations in a row, early July of 2016 and September of 2015. We simply love it! The owners are incredible and so helpful from start to finish. Our family absolutely loves to hunt for sea glass and this place is the absolute best for that hobby. I have never seen so much sea glass. (Perhaps I shouldn't reveal this so no one else scoops it up!) We ran into an issue when the TVs didn't work for a day or two and the owners were super responsive. A storm had caused some issues in the area (nothing that could be done until it was fixed via the cable company). But the owners were so good at keeping us updated and are just truly nice folks. The house itself is big and well equipped. We love the deck and the big yard and of course, the beach. The neighbors are nice too! I didn't even get attacked by any black flies this past summer! Ha! We didn't have issues with any bugs and the kids truly enjoyed the treasure hunt we put together for them on the grounds. We did end up driving quite a distance to a community pool as it was really hot in July and our son LOVES swimming, but doesn't so much love swimming in the Bay. :) We would highly recommend this place to anyone. We can't wait to come back. Thank you for sharing your home with us and let me know if you decide to sell. Ha!
                                                                            • Submitted: Jan 8, 2017
                                                                            • Stayed: Jul 2016

                                                                            The place was clean and close to town.

                                                                            4 of 5
                                                                            Clean place and close to town. Nice big backyard which we didn't end up using due to the weather. We enjoyed our stay and Ann was very hospitable.
                                                                            • Submitted: Oct 16, 2016
                                                                            • Stayed: Oct 2016

                                                                            Great girls weekend!

                                                                            5 of 5
                                                                            We had a great girls weekend in Chestertown! The house was perfect! Plenty of room, everything we needed. Kitchen was well equipped. Easy walk into town
                                                                            • Submitted: Sep 29, 2016
                                                                            • Stayed: Sep 2016