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    • 4 BR
    • 2 BA
    • Sleeps 8
    House #316300ha
    39
      Excellent! 4.7/5
      (58 reviews)
      avg/night
      • 3 BR
      • 2 BA
      • Sleeps 6
      Condo #133608
      58
        Exceptional! 5/5
        (55 reviews)
        avg/night
        • 3 BR
        • 3 BA
        • Sleeps 8
        House #294688
        55
          Exceptional! 5/5
          (40 reviews)
          avg/night
          • 2 BR
          • 1 BA
          • Sleeps 4
          Cottage #820614
          40
            • 4 BR
            • 3 BA
            • 1 HF BA
            • Sleeps 9
            House #324062
            1
              Exceptional! 5/5
              (24 reviews)
              avg/night
              • 5 BR
              • 3 BA
              • Sleeps 12
              House #750777
              24
                • 3 BR
                • 2 BA
                • Sleeps 6
                House #900086ha
                32
                  • 2 BR
                  • 1 BA
                  • 1 HF BA
                  • Sleeps 6
                  Townhome #623485
                  35
                    Exceptional! 5/5
                    (16 reviews)
                    avg/night
                    • 2 BR
                    • 1 BA
                    • Sleeps 6
                    House #4176147ha
                    16
                      • 4 BR
                      • 2 BA
                      • Sleeps 9
                      House #306997
                      48
                        • 4 BR
                        • 4 BA
                        • Sleeps 14
                        House #241350ha
                        58
                          Wonderful! 4.9/5
                          (41 reviews)
                          avg/night
                          • 1 BR
                          • 1 BA
                          • Sleeps 5
                          Apartment #435647
                          41
                            Wonderful! 4.9/5
                            (24 reviews)
                            avg/night
                            • 3 BR
                            • 2 BA
                            • 1 HF BA
                            • Sleeps 6
                            Cottage #482154
                            24
                              • 4 BR
                              • 3 BA
                              • Sleeps 8
                              House #684953
                              30
                                Exceptional! 5/5
                                (46 reviews)
                                avg/night
                                • 4 BR
                                • 3 BA
                                • 1 HF BA
                                • Sleeps 9
                                House #700188
                                46
                                  • 3 BR
                                  • 2 BA
                                  • Sleeps 7
                                  House #361241
                                  92
                                    • 5 BR
                                    • 4 BA
                                    • Sleeps 18
                                    House #581725
                                    18
                                      Wonderful! 4.8/5
                                      (15 reviews)
                                      avg/night
                                      • 2 BR
                                      • 1 BA
                                      • Sleeps 4
                                      Apartment #918862
                                      15
                                        Wonderful! 4.8/5
                                        (30 reviews)
                                        avg/night
                                        • 2 BR
                                        • 1 BA
                                        • 1 HF BA
                                        • Sleeps 4
                                        Cottage #599767
                                        30
                                          • 3 BR
                                          • 3 BA
                                          • 1 HF BA
                                          • Sleeps 7
                                          House #958803
                                          4
                                            Wonderful! 4.8/5
                                            (5 reviews)
                                            avg/night
                                            • 3 BR
                                            • 3 BA
                                            • Sleeps 6
                                            House #1010708
                                            5
                                              • 3 BR
                                              • 2 BA
                                              • 1 HF BA
                                              • Sleeps 8
                                              House #458610
                                              65
                                                • 5 BR
                                                • 3 BA
                                                • Sleeps 14
                                                House #617890
                                                22
                                                  • 1 BR
                                                  • 1 BA
                                                  • 1 HF BA
                                                  • Sleeps 4
                                                  Apartment #844031
                                                  10
                                                    • 4 BR
                                                    • 4 BA
                                                    • Sleeps 8
                                                    House #432739
                                                    70
                                                      • 2 BR
                                                      • 1 BA
                                                      • Sleeps 5
                                                      Apartment #744282
                                                      35
                                                        • 4 BR
                                                        • 3 BA
                                                        • 1 HF BA
                                                        • Sleeps 10
                                                        House #432131
                                                        84
                                                          Exceptional! 5/5
                                                          (11 reviews)
                                                          avg/night
                                                          • 3 BR
                                                          • 2 BA
                                                          • 1 HF BA
                                                          • Sleeps 6
                                                          House #4069765ha
                                                          11
                                                            Exceptional! 5/5
                                                            (31 reviews)
                                                            avg/night
                                                            • 4 BR
                                                            • 2 BA
                                                            • Sleeps 12
                                                            House #371050
                                                            31
                                                              • 4 BR
                                                              • 2 BA
                                                              • Sleeps 10
                                                              House #807108
                                                              4
                                                                • 4 BR
                                                                • 2 BA
                                                                • 1 HF BA
                                                                • Sleeps 11
                                                                House #824386
                                                                7
                                                                  • 3 BR
                                                                  • 2 BA
                                                                  • Sleeps 9
                                                                  Apartment #409821
                                                                  11
                                                                    Wonderful! 4.9/5
                                                                    (24 reviews)
                                                                    avg/night
                                                                    • 5 BR
                                                                    • 3 BA
                                                                    • Sleeps 10
                                                                    House #713006
                                                                    24
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Sleeps 9
                                                                      House #461541
                                                                      90
                                                                        • 4 BR
                                                                        • 3 BA
                                                                        • Sleeps 12
                                                                        House #3786046ha
                                                                        16
                                                                          • 4 BR
                                                                          • 2 BA
                                                                          • Sleeps 10
                                                                          House #3771110ha
                                                                          15
                                                                            Wonderful! 4.9/5
                                                                            (19 reviews)
                                                                            avg/night
                                                                            • 5 BR
                                                                            • 2 BA
                                                                            • 2 HF BA
                                                                            • Sleeps 11
                                                                            House #360959ha
                                                                            19
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • 1 HF BA
                                                                              • Sleeps 10
                                                                              Chalet #905951ha
                                                                              25
                                                                                • 2 BR
                                                                                • 1 BA
                                                                                • 2 HF BA
                                                                                • Sleeps 5
                                                                                Cottage #844888
                                                                                11
                                                                                  • 6 BR
                                                                                  • 3 BA
                                                                                  • 1 HF BA
                                                                                  • Sleeps 9
                                                                                  House #198445
                                                                                  30
                                                                                    Exceptional! 5/5
                                                                                    (20 reviews)
                                                                                    avg/night
                                                                                    • 2 BR
                                                                                    • 1 BA
                                                                                    • 1 HF BA
                                                                                    • Sleeps 5
                                                                                    Townhome #693991
                                                                                    20
                                                                                      • 4 BR
                                                                                      • 3 BA
                                                                                      • Sleeps 10
                                                                                      House #40646
                                                                                      43
                                                                                        Exceptional! 5/5
                                                                                        (24 reviews)
                                                                                        avg/night
                                                                                        • 2 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 5
                                                                                        Cottage #608459
                                                                                        24
                                                                                          • 3 BR
                                                                                          • 2 BA
                                                                                          • 2 HF BA
                                                                                          • Sleeps 10
                                                                                          House #989211ha
                                                                                          21
                                                                                            • 3 BR
                                                                                            • 3 BA
                                                                                            • Sleeps 8
                                                                                            House #60381
                                                                                            16
                                                                                              • 3 BR
                                                                                              • 2 BA
                                                                                              • 1 HF BA
                                                                                              • Sleeps 9
                                                                                              House #131054
                                                                                              91
                                                                                                • 5 BR
                                                                                                • 4 BA
                                                                                                • 1 HF BA
                                                                                                • Sleeps 14
                                                                                                House #618954
                                                                                                62
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • 1 HF BA
                                                                                                  • Sleeps 8
                                                                                                  House #3946470ha
                                                                                                  12
                                                                                                    • 5 BR
                                                                                                    • 5 BA
                                                                                                    • Sleeps 10
                                                                                                    Lodge #3920901ha
                                                                                                    18
                                                                                                      Wonderful! 4.8/5
                                                                                                      (12 reviews)
                                                                                                      avg/night
                                                                                                      • 8 BR
                                                                                                      • 5 BA
                                                                                                      • Sleeps 12
                                                                                                      Estate #3957742ha
                                                                                                      12
                                                                                                      • 1 - 50 of 300+
                                                                                                       

                                                                                                      Recent Chester Reviews

                                                                                                      Family friendly fun

                                                                                                      5 of 5
                                                                                                      What a great place to celebrate our grandson’s first birthday with family and friends! Also enjoyed fishing and crabbing from the dock; relaxing on the deck viewing the osprey and heron; and watching the lights on the boats in the evening. Great dinner at nearby Cantler's Riverside Inn and ice cream at the Annapolis Ice Cream Company. Wonderful for a laid back vacation.
                                                                                                      • Submitted: Jun 18, 2017
                                                                                                      • Stayed: Jun 2017

                                                                                                      Beautiful home, spotlessly clean! Just the perfect setting indoor and out for relaxing with family!

                                                                                                      5 of 5
                                                                                                      Don't hesitate to book this! I'm already planning a get together here for next year, and will consider myself lucky if I'm able to get this house again!
                                                                                                      • Submitted: Jun 13, 2017
                                                                                                      • Stayed: Jun 2017