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Additional fees apply. Taxes may be added.
    Exceptional! 5/5
    (7 reviews)
    $234
    avg/night
    • 3 BR
    • 2 BA
    • Sleeps 6
    House #759063
    7
      $510
      avg/night
      • 4 BR
      • 3 BA
      • Sleeps 8
      House #4487352ha
      1
      Viewed 11 times in the last 48 hours
        $210
        avg/night
        • 4 BR
        • 2 BA
        • 1 HF BA
        • Sleeps 8
        House #4558937ha
        Viewed 13 times in the last 48 hours
          $600
          avg/night
          • 4 BR
          • 3 BA
          • Sleeps 8
          House #1054955
          Viewed 50 times in the last 48 hours
            $150
            avg/night
            • 1 BR
            • 1 BA
            • Sleeps 2
            Apartment #975033
            Viewed 15 times in the last 48 hours
              Exceptional! 5/5
              (55 reviews)
              $295
              avg/night
              • 3 BR
              • 3 BA
              • Sleeps 8
              House #294688
              55
              Viewed 42 times in the last 48 hours
                Wonderful! 4.9/5
                (10 reviews)
                $96
                avg/night
                • 1 BR
                • 1 BA
                • 1 HF BA
                • Sleeps 4
                Apartment #844031
                10
                Viewed 33 times in the last 48 hours
                  Exceptional! 5/5
                  (7 reviews)
                  $269
                  avg/night
                  • 3 BR
                  • 2 BA
                  • Sleeps 8
                  Cottage #883977
                  7
                  Viewed 31 times in the last 48 hours
                    Exceptional! 5/5
                    (40 reviews)
                    $505
                    avg/night
                    • 4 BR
                    • 4 BA
                    • 1 HF BA
                    • Sleeps 13
                    House #356548
                    40
                    Viewed 18 times in the last 48 hours
                      Wonderful! 4.9/5
                      (11 reviews)
                      $150
                      avg/night
                      • 3 BR
                      • 2 BA
                      • Sleeps 9
                      Apartment #409821
                      11
                      Viewed 24 times in the last 48 hours
                        Wonderful! 4.8/5
                        (16 reviews)
                        $439
                        avg/night
                        • 4 BR
                        • 3 BA
                        • Sleeps 12
                        House #3786046ha
                        16
                        Viewed 31 times in the last 48 hours
                          Exceptional! 5/5
                          (24 reviews)
                          $255
                          avg/night
                          • 2 BR
                          • 2 BA
                          • Sleeps 5
                          Cottage #608459
                          24
                          Viewed 35 times in the last 48 hours
                            Excellent! 4.7/5
                            (21 reviews)
                            $223
                            avg/night
                            • 4 BR
                            • 2 BA
                            • Sleeps 10
                            House #704799
                            21
                            Viewed 29 times in the last 48 hours
                              Exceptional! 5/5
                              (20 reviews)
                              $237
                              avg/night
                              • 3 BR
                              • 2 BA
                              • 1 HF BA
                              • Sleeps 8
                              Cottage #503705
                              20
                              Viewed 24 times in the last 48 hours
                                Wonderful! 4.9/5
                                (13 reviews)
                                $240
                                avg/night
                                • 4 BR
                                • 2 BA
                                • Sleeps 10
                                House #398147
                                13
                                Viewed 40 times in the last 48 hours
                                  Excellent! 4.6/5
                                  (31 reviews)
                                  $170
                                  avg/night
                                  • 3 BR
                                  • 1 BA
                                  • 1 HF BA
                                  • Sleeps 7
                                  House #429782
                                  31
                                  Viewed 28 times in the last 48 hours
                                    Excellent! 4.6/5
                                    (32 reviews)
                                    $383
                                    avg/night
                                    • 3 BR
                                    • 2 BA
                                    • Sleeps 12
                                    House #7002752ha
                                    32
                                    Viewed 47 times in the last 48 hours
                                      Wonderful! 4.8/5
                                      (26 reviews)
                                      $314
                                      avg/night
                                      • 2 BR
                                      • 1 BA
                                      • 1 HF BA
                                      • Sleeps 6
                                      House #431733
                                      26
                                      Viewed 37 times in the last 48 hours
                                        Wonderful! 4.9/5
                                        (31 reviews)
                                        $100
                                        avg/night
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 5
                                        Apartment #494798
                                        31
                                        Viewed 21 times in the last 48 hours
                                          Exceptional! 5/5
                                          (7 reviews)
                                          $217
                                          avg/night
                                          • 3 BR
                                          • 2 BA
                                          • 1 HF BA
                                          • Sleeps 8
                                          House #797359
                                          7
                                          Viewed 18 times in the last 48 hours
                                            Excellent! 4.7/5
                                            (15 reviews)
                                            $300
                                            avg/night
                                            • 6 BR
                                            • 2 BA
                                            • Sleeps 11
                                            House #235930ha
                                            15
                                            Viewed 36 times in the last 48 hours
                                              Wonderful! 4.9/5
                                              (10 reviews)
                                              $173
                                              avg/night
                                              • 3 BR
                                              • 1 BA
                                              • 1 HF BA
                                              • Sleeps 8
                                              House #571411
                                              10
                                              Viewed 18 times in the last 48 hours
                                                $271
                                                avg/night
                                                • 3 BR
                                                • 1 BA
                                                • Sleeps 8
                                                House #440251
                                                2
                                                Viewed 20 times in the last 48 hours
                                                  Wonderful! 4.9/5
                                                  (14 reviews)
                                                  $303
                                                  avg/night
                                                  • 4 BR
                                                  • 2 BA
                                                  • Sleeps 8
                                                  Estate #730130
                                                  14
                                                  Viewed 67 times in the last 48 hours
                                                    Exceptional! 5/5
                                                    (6 reviews)
                                                    $297
                                                    avg/night
                                                    • 2 BR
                                                    • 1 BA
                                                    • Sleeps 4
                                                    Chateau / Country House #738311
                                                    6
                                                    Viewed 18 times in the last 48 hours
                                                      $300
                                                      avg/night
                                                      • 4 BR
                                                      • 2 BA
                                                      • Sleeps 10
                                                      Farmhouse #598989
                                                      2
                                                      Viewed 45 times in the last 48 hours
                                                        $150
                                                        avg/night
                                                        • 1 BR
                                                        • 1 BA
                                                        • Sleeps 3
                                                        Apartment #589368
                                                        4
                                                        Viewed 16 times in the last 48 hours
                                                          Exceptional! 5/5
                                                          (11 reviews)
                                                          $229
                                                          avg/night
                                                          • 3 BR
                                                          • 2 BA
                                                          • Sleeps 6
                                                          House #220506
                                                          11
                                                          Viewed 12 times in the last 48 hours
                                                            $333
                                                            avg/night
                                                            • 4 BR
                                                            • 2 BA
                                                            • Sleeps 8
                                                            House #3917327ha
                                                            2
                                                            Viewed 17 times in the last 48 hours
                                                              Excellent! 4.5/5
                                                              (11 reviews)
                                                              $200
                                                              avg/night
                                                              • 3 BR
                                                              • 2 BA
                                                              • Sleeps 9
                                                              House #706116
                                                              11
                                                              Viewed 17 times in the last 48 hours
                                                                Wonderful! 4.9/5
                                                                (19 reviews)
                                                                $214
                                                                avg/night
                                                                • 2 BR
                                                                • 1 BA
                                                                • Sleeps 6
                                                                House #53282
                                                                19
                                                                Viewed 47 times in the last 48 hours
                                                                  Wonderful! 4.8/5
                                                                  (22 reviews)
                                                                  $264
                                                                  avg/night
                                                                  • 3 BR
                                                                  • 1 BA
                                                                  • Sleeps 6
                                                                  Cottage #418738
                                                                  22
                                                                  Viewed 27 times in the last 48 hours
                                                                    Wonderful! 4.9/5
                                                                    (29 reviews)
                                                                    $614
                                                                    avg/night
                                                                    • 4 BR
                                                                    • 4 BA
                                                                    • Sleeps 8
                                                                    House #410328
                                                                    29
                                                                    Viewed 24 times in the last 48 hours
                                                                      Wonderful! 4.9/5
                                                                      (8 reviews)
                                                                      $700
                                                                      avg/night
                                                                      • 4 BR
                                                                      • 3 BA
                                                                      • 1 HF BA
                                                                      • Sleeps 8
                                                                      House #458295
                                                                      8
                                                                      Viewed 45 times in the last 48 hours
                                                                        Wonderful! 4.8/5
                                                                        (19 reviews)
                                                                        $590
                                                                        avg/night
                                                                        • 4 BR
                                                                        • 4 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 10
                                                                        Estate #606821
                                                                        19
                                                                        Viewed 23 times in the last 48 hours
                                                                          Wonderful! 4.9/5
                                                                          (9 reviews)
                                                                          $300
                                                                          avg/night
                                                                          • 5 BR
                                                                          • 2 BA
                                                                          • Sleeps 10
                                                                          Farmhouse #582873
                                                                          9
                                                                          Viewed 14 times in the last 48 hours
                                                                            $197
                                                                            avg/night
                                                                            • 2 BR
                                                                            • 1 BA
                                                                            • Sleeps 4
                                                                            Apartment #1045032
                                                                            Viewed 33 times in the last 48 hours
                                                                              Exceptional! 5/5
                                                                              (5 reviews)
                                                                              $999
                                                                              avg/night
                                                                              • 7 BR
                                                                              • 4 BA
                                                                              • 1 HF BA
                                                                              • Sleeps 13
                                                                              House #935769
                                                                              5
                                                                              Viewed 27 times in the last 48 hours
                                                                                $59
                                                                                avg/night
                                                                                • 8 BR
                                                                                • 8 BA
                                                                                • Sleeps 4
                                                                                Hotel #4093884ha
                                                                                Viewed 14 times in the last 48 hours
                                                                                  $217
                                                                                  avg/night
                                                                                  • 3 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 8
                                                                                  House #4204088ha
                                                                                  1
                                                                                  Viewed 12 times in the last 48 hours
                                                                                    Exceptional! 5/5
                                                                                    (9 reviews)
                                                                                    $211
                                                                                    avg/night
                                                                                    • 2 BR
                                                                                    • 1 BA
                                                                                    • 1 HF BA
                                                                                    • Sleeps 4
                                                                                    House #473897
                                                                                    9
                                                                                    Viewed 8 times in the last 48 hours
                                                                                      $157
                                                                                      avg/night
                                                                                      • 2 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 5
                                                                                      House #4112420ha
                                                                                      1
                                                                                        $37
                                                                                        avg/night
                                                                                        • Studio
                                                                                        • 1 BA
                                                                                        • Sleeps 2
                                                                                        House #4533503ha
                                                                                        Viewed 6 times in the last 48 hours
                                                                                          $1,171
                                                                                          avg/night
                                                                                          • 6 BR
                                                                                          • 4 BA
                                                                                          • 1 HF BA
                                                                                          • Sleeps 11
                                                                                          Estate #1015635
                                                                                          Viewed 15 times in the last 48 hours
                                                                                            $969
                                                                                            avg/night
                                                                                            • 4 BR
                                                                                            • 2 BA
                                                                                            • 1 HF BA
                                                                                            • Sleeps 11
                                                                                            House #592542
                                                                                              $217
                                                                                              avg/night
                                                                                              • 3 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 6
                                                                                              House #4247910ha
                                                                                              Viewed 19 times in the last 48 hours
                                                                                                $1,208
                                                                                                avg/night
                                                                                                • 4 BR
                                                                                                • 4 BA
                                                                                                • Sleeps 10
                                                                                                House #732410
                                                                                                  $667
                                                                                                  avg/night
                                                                                                  • 4 BR
                                                                                                  • 4 BA
                                                                                                  • Sleeps 8
                                                                                                  House #4176971ha
                                                                                                  Viewed 21 times in the last 48 hours
                                                                                                    $667
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 7
                                                                                                    House #1078296
                                                                                                      $43
                                                                                                      avg/night
                                                                                                      • 1 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 10
                                                                                                      Recreational Vehicle #4243662ha
                                                                                                      Viewed 40 times in the last 48 hours
                                                                                                      • 1 - 50 of 61

                                                                                                      Chestertown (61)

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                                                                                                      Recent Chestertown Reviews

                                                                                                      View property

                                                                                                      Wonderful waterfront property

                                                                                                      5 of 5
                                                                                                      Everything about the house, location, and setting is truly great! The house is very well appointed, updated, and had everything we needed to enjoy a long Memorial Day weekend. The house is walking distance to downtown (around a mile) and over the bridge. The water view is fantastic and the porch was a great setting to hang out and relax. We would definitely stay here again and the owners were very communicative and accommodating. Highly recommend.
                                                                                                      ... continue reading
                                                                                                      • Submitted: Jun 07, 2017
                                                                                                      • Stayed: May 2017
                                                                                                      View property

                                                                                                      Lovely owner and great property

                                                                                                      4 of 5
                                                                                                      We stayed here over Christmas holidays while visiting family on Kent Island. The property is beautifully situated on the Bay. The house was clean and we found everything we needed--great wi-fi, dish TV. The best part was that we were able to bring our dogs. One of the dogs is older and doesn't like the kennel and the other dog is feral rescue and is terrified of people so it's great to be able to bring them with us. The weather was horrendous the whole time we were there, which is of no fault of the owner but we did wind up leaving a day earlier than expected. With good weather, this would be an exceptionally beautiful place! The owner went out of her way to make sure there was a Christmas tree and decorations. Very thoughtful.
                                                                                                      ... continue reading
                                                                                                      • Submitted: Jun 06, 2017
                                                                                                      • Stayed: Dec 2015