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  • Showing 1-50 of 300+
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Additional fees apply. Taxes may be added.
    Excellent! 4.7/5
    (63 reviews)
    avg/night
    Condo #133608vb
    • 3 BR
    • 2 BA
    • Sleeps 6
    63
    Viewed 11 times in the last 48 hours

    Confirmation within 24 hours

    Your booking request will be confirmed or denied within 24 hours.

      Wonderful! 4.9/5
      (37 reviews)
      avg/night
      Townhome #623485vb
      • 2 BR
      • 1 BA
      • 1 HF BA
      • Sleeps 6
      37
      Viewed 9 times in the last 48 hours

      Confirmation within 24 hours

      Your booking request will be confirmed or denied within 24 hours.

        Wonderful! 4.8/5
        (18 reviews)
        avg/night
        Apartment #918862vb
        • 2 BR
        • 1 BA
        • Sleeps 4
        18
        Viewed 6 times in the last 48 hours

        Confirmation within 24 hours

        Your booking request will be confirmed or denied within 24 hours.

          Excellent! 4.7/5
          (49 reviews)
          avg/night
          House #306997vb
          • 4 BR
          • 2 BA
          • Sleeps 9
          49
          Viewed 31 times in the last 48 hours

          Confirmation within 24 hours

          Your booking request will be confirmed or denied within 24 hours.

            Exceptional! 5/5
            (21 reviews)
            avg/night
            House #4176147
            • 2 BR
            • 1 BA
            • Sleeps 6
            21
            Viewed 23 times in the last 48 hours

            Confirmation within 24 hours

            Your booking request will be confirmed or denied within 24 hours.

              Wonderful! 4.8/5
              (61 reviews)
              avg/night
              House #241350
              • 4 BR
              • 4 BA
              • Sleeps 14
              61
              Viewed 26 times in the last 48 hours

              Confirmation within 24 hours

              Your booking request will be confirmed or denied within 24 hours.

                Exceptional! 5/5
                (67 reviews)
                avg/night
                House #458610vb
                • 3 BR
                • 2 BA
                • 1 HF BA
                • Sleeps 8
                67
                Viewed 9 times in the last 48 hours

                Confirmation within 24 hours

                Your booking request will be confirmed or denied within 24 hours.

                  Exceptional! 5/5
                  (51 reviews)
                  avg/night
                  House #700188vb
                  • 4 BR
                  • 3 BA
                  • 1 HF BA
                  • Sleeps 9
                  51
                  Viewed 9 times in the last 48 hours

                  Confirmation within 24 hours

                  Your booking request will be confirmed or denied within 24 hours.

                    Wonderful! 4.9/5
                    (25 reviews)
                    avg/night
                    House #713006vb
                    • 5 BR
                    • 3 BA
                    • Sleeps 10
                    25
                    Viewed 6 times in the last 48 hours

                    Confirmation within 24 hours

                    Your booking request will be confirmed or denied within 24 hours.

                      Wonderful! 4.9/5
                      (41 reviews)
                      avg/night
                      Apartment #435647vb
                      • 1 BR
                      • 1 BA
                      • Sleeps 5
                      41

                      Confirmation within 24 hours

                      Your booking request will be confirmed or denied within 24 hours.

                        Wonderful! 4.9/5
                        (38 reviews)
                        avg/night
                        Apartment #744282vb
                        • 2 BR
                        • 1 BA
                        • Sleeps 5
                        38
                        Viewed 8 times in the last 48 hours

                        Confirmation within 24 hours

                        Your booking request will be confirmed or denied within 24 hours.

                          Exceptional! 5/5
                          (9 reviews)
                          avg/night
                          House #824386vb
                          • 4 BR
                          • 2 BA
                          • 1 HF BA
                          • Sleeps 11
                          9
                          Viewed 7 times in the last 48 hours

                          Confirmation within 24 hours

                          Your booking request will be confirmed or denied within 24 hours.

                            Wonderful! 4.9/5
                            (26 reviews)
                            avg/night
                            Chalet #905951
                            • 3 BR
                            • 2 BA
                            • 1 HF BA
                            • Sleeps 10
                            26
                            Viewed 25 times in the last 48 hours

                            Confirmation within 24 hours

                            Your booking request will be confirmed or denied within 24 hours.

                              Exceptional! 5/5
                              (94 reviews)
                              avg/night
                              House #461541vb
                              • 3 BR
                              • 2 BA
                              • Sleeps 9
                              94
                              Viewed 15 times in the last 48 hours

                              Confirmation within 24 hours

                              Your booking request will be confirmed or denied within 24 hours.

                                Exceptional! 5/5
                                (22 reviews)
                                avg/night
                                Townhome #693991vb
                                • 2 BR
                                • 1 BA
                                • 1 HF BA
                                • Sleeps 5
                                22

                                Confirmation within 24 hours

                                Your booking request will be confirmed or denied within 24 hours.

                                  Wonderful! 4.9/5
                                  (95 reviews)
                                  avg/night
                                  House #361241vb
                                  • 3 BR
                                  • 2 BA
                                  • Sleeps 7
                                  95
                                  Viewed 10 times in the last 48 hours

                                  Instant confirmation

                                  Your booking request will be confirmed immediately.

                                    House #60381vb
                                    • 3 BR
                                    • 3 BA
                                    • Sleeps 8
                                    18

                                    Confirmation within 24 hours

                                    Your booking request will be confirmed or denied within 24 hours.

                                      Wonderful! 4.8/5
                                      (23 reviews)
                                      avg/night
                                      House #989211
                                      • 3 BR
                                      • 2 BA
                                      • 2 HF BA
                                      • Sleeps 10
                                      23
                                      Viewed 10 times in the last 48 hours

                                      Confirmation within 24 hours

                                      Your booking request will be confirmed or denied within 24 hours.

                                        Exceptional! 5/5
                                        (66 reviews)
                                        avg/night
                                        House #618954vb
                                        • 5 BR
                                        • 4 BA
                                        • 1 HF BA
                                        • Sleeps 14
                                        66
                                        Viewed 13 times in the last 48 hours

                                        Instant confirmation

                                        Your booking request will be confirmed immediately.

                                          Exceptional! 5/5
                                          (26 reviews)
                                          avg/night
                                          Townhome #683864vb
                                          • 3 BR
                                          • 3 BA
                                          • 1 HF BA
                                          • Sleeps 6
                                          26
                                          Viewed 11 times in the last 48 hours

                                          Instant confirmation

                                          Your booking request will be confirmed immediately.

                                            Wonderful! 4.9/5
                                            (32 reviews)
                                            avg/night
                                            House #900086
                                            • 3 BR
                                            • 2 BA
                                            • Sleeps 6
                                            32
                                            Viewed 10 times in the last 48 hours

                                            Confirmation within 24 hours

                                            Your booking request will be confirmed or denied within 24 hours.

                                              Townhome #924338vb
                                              • 2 BR
                                              • 2 BA
                                              • 1 HF BA
                                              • Sleeps 6
                                              9

                                              Confirmation within 24 hours

                                              Your booking request will be confirmed or denied within 24 hours.

                                                Wonderful! 4.9/5
                                                (91 reviews)
                                                avg/night
                                                House #131054vb
                                                • 3 BR
                                                • 2 BA
                                                • 1 HF BA
                                                • Sleeps 9
                                                91
                                                Viewed 12 times in the last 48 hours

                                                Confirmation within 24 hours

                                                Your booking request will be confirmed or denied within 24 hours.

                                                  Wonderful! 4.9/5
                                                  (41 reviews)
                                                  avg/night
                                                  Apartment #422800vb
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 5
                                                  41

                                                  Confirmation within 24 hours

                                                  Your booking request will be confirmed or denied within 24 hours.

                                                    Wonderful! 4.9/5
                                                    (15 reviews)
                                                    avg/night
                                                    House #3946470
                                                    • 3 BR
                                                    • 2 BA
                                                    • 1 HF BA
                                                    • Sleeps 8
                                                    15
                                                    Viewed 9 times in the last 48 hours

                                                    Confirmation within 24 hours

                                                    Your booking request will be confirmed or denied within 24 hours.

                                                      Apartment #663401vb
                                                      • 2 BR
                                                      • 1 BA
                                                      • Sleeps 4
                                                      Viewed 6 times in the last 48 hours

                                                      Confirmation within 24 hours

                                                      Your booking request will be confirmed or denied within 24 hours.

                                                        Wonderful! 4.9/5
                                                        (27 reviews)
                                                        avg/night
                                                        Apartment #724465vb
                                                        • 2 BR
                                                        • 1 BA
                                                        • Sleeps 5
                                                        27
                                                        Viewed 6 times in the last 48 hours

                                                        Confirmation within 24 hours

                                                        Your booking request will be confirmed or denied within 24 hours.

                                                          Exceptional! 5/5
                                                          (27 reviews)
                                                          avg/night
                                                          Townhome #811296vb
                                                          • 3 BR
                                                          • 2 BA
                                                          • 1 HF BA
                                                          • Sleeps 8
                                                          27

                                                          Confirmation within 24 hours

                                                          Your booking request will be confirmed or denied within 24 hours.

                                                            House #4477093
                                                            • 4 BR
                                                            • 1 BA
                                                            • 1 HF BA
                                                            • Sleeps 6

                                                            Confirmation within 24 hours

                                                            Your booking request will be confirmed or denied within 24 hours.

                                                              Exceptional! 5/5
                                                              (5 reviews)
                                                              avg/night
                                                              Apartment #882518vb
                                                              • 1 BR
                                                              • 1 BA
                                                              • Sleeps 4
                                                              5

                                                              Confirmation within 24 hours

                                                              Your booking request will be confirmed or denied within 24 hours.

                                                                House #209767vb
                                                                • 2 BR
                                                                • 1 BA
                                                                • 1 HF BA
                                                                • Sleeps 5
                                                                34

                                                                Confirmation within 24 hours

                                                                Your booking request will be confirmed or denied within 24 hours.

                                                                  Exceptional! 5/5
                                                                  (33 reviews)
                                                                  avg/night
                                                                  House #345765
                                                                  • 3 BR
                                                                  • 3 BA
                                                                  • 2 HF BA
                                                                  • Sleeps 12
                                                                  33
                                                                  Viewed 14 times in the last 48 hours

                                                                  Confirmation within 24 hours

                                                                  Your booking request will be confirmed or denied within 24 hours.

                                                                    Wonderful! 4.9/5
                                                                    (20 reviews)
                                                                    avg/night
                                                                    House #346388
                                                                    • 2 BR
                                                                    • 2 BA
                                                                    • 1 HF BA
                                                                    • Sleeps 6
                                                                    20
                                                                    Viewed 7 times in the last 48 hours

                                                                    Confirmation within 24 hours

                                                                    Your booking request will be confirmed or denied within 24 hours.

                                                                      House #283626vb
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • 1 HF BA
                                                                      • Sleeps 8
                                                                      11

                                                                      Confirmation within 24 hours

                                                                      Your booking request will be confirmed or denied within 24 hours.

                                                                        Wonderful! 4.9/5
                                                                        (7 reviews)
                                                                        avg/night
                                                                        Apartment #904015vb
                                                                        • 1 BR
                                                                        • 1 BA
                                                                        • Sleeps 4
                                                                        7
                                                                        Viewed 6 times in the last 48 hours

                                                                        Instant confirmation

                                                                        Your booking request will be confirmed immediately.

                                                                          Wonderful! 4.9/5
                                                                          (38 reviews)
                                                                          avg/night
                                                                          House #655455vb
                                                                          • 3 BR
                                                                          • 1 BA
                                                                          • Sleeps 8
                                                                          38
                                                                          Viewed 17 times in the last 48 hours

                                                                          Confirmation within 24 hours

                                                                          Your booking request will be confirmed or denied within 24 hours.

                                                                            Apartment #775994vb
                                                                            • 1 BR
                                                                            • 1 BA
                                                                            • Sleeps 6
                                                                            11

                                                                            Confirmation within 24 hours

                                                                            Your booking request will be confirmed or denied within 24 hours.

                                                                              Wonderful! 4.8/5
                                                                              (17 reviews)
                                                                              avg/night
                                                                              Cottage #3884479
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 8
                                                                              17
                                                                              Viewed 22 times in the last 48 hours

                                                                              Confirmation within 24 hours

                                                                              Your booking request will be confirmed or denied within 24 hours.

                                                                                Townhome #915256vb
                                                                                • 3 BR
                                                                                • 1 BA
                                                                                • 1 HF BA
                                                                                • Sleeps 6
                                                                                3

                                                                                Confirmation within 24 hours

                                                                                Your booking request will be confirmed or denied within 24 hours.

                                                                                  Excellent! 4.7/5
                                                                                  (30 reviews)
                                                                                  avg/night
                                                                                  Cottage #151554
                                                                                  • 2 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                  30
                                                                                  Viewed 5 times in the last 48 hours

                                                                                  Confirmation within 24 hours

                                                                                  Your booking request will be confirmed or denied within 24 hours.

                                                                                    House #3895721
                                                                                    • 4 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 9
                                                                                    15

                                                                                    Confirmation within 24 hours

                                                                                    Your booking request will be confirmed or denied within 24 hours.

                                                                                      Wonderful! 4.9/5
                                                                                      (13 reviews)
                                                                                      avg/night
                                                                                      House #483668vb
                                                                                      • 2 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 6
                                                                                      13
                                                                                      Viewed 8 times in the last 48 hours

                                                                                      Confirmation within 24 hours

                                                                                      Your booking request will be confirmed or denied within 24 hours.

                                                                                        Wonderful! 4.9/5
                                                                                        (13 reviews)
                                                                                        avg/night
                                                                                        House #462887vb
                                                                                        • 3 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 9
                                                                                        13
                                                                                        Viewed 6 times in the last 48 hours

                                                                                        Confirmation within 24 hours

                                                                                        Your booking request will be confirmed or denied within 24 hours.

                                                                                          House #837146vb
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • 1 HF BA
                                                                                          • Sleeps 6
                                                                                          4

                                                                                          Confirmation within 24 hours

                                                                                          Your booking request will be confirmed or denied within 24 hours.

                                                                                            Wonderful! 4.8/5
                                                                                            (12 reviews)
                                                                                            avg/night
                                                                                            House #490595vb
                                                                                            • Studio
                                                                                            • 2 BA
                                                                                            • Sleeps 18
                                                                                            12
                                                                                            Viewed 21 times in the last 48 hours

                                                                                            Confirmation within 24 hours

                                                                                            Your booking request will be confirmed or denied within 24 hours.

                                                                                              avg/night
                                                                                              House #560536vb
                                                                                              • 4 BR
                                                                                              • 2 BA
                                                                                              • 1 HF BA
                                                                                              • Sleeps 8
                                                                                              4
                                                                                              Viewed 13 times in the last 48 hours

                                                                                              Confirmation within 24 hours

                                                                                              Your booking request will be confirmed or denied within 24 hours.

                                                                                                Exceptional! 5/5
                                                                                                (17 reviews)
                                                                                                avg/night
                                                                                                House #671203vb
                                                                                                • 5 BR
                                                                                                • 3 BA
                                                                                                • 1 HF BA
                                                                                                • Sleeps 10
                                                                                                17
                                                                                                Viewed 19 times in the last 48 hours

                                                                                                Confirmation within 24 hours

                                                                                                Your booking request will be confirmed or denied within 24 hours.

                                                                                                  House #1024646vb
                                                                                                  • 4 BR
                                                                                                  • 3 BA
                                                                                                  • Sleeps 10
                                                                                                  3

                                                                                                  Confirmation within 24 hours

                                                                                                  Your booking request will be confirmed or denied within 24 hours.

                                                                                                    House #1029179vb
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • 1 HF BA
                                                                                                    • Sleeps 8

                                                                                                    Confirmation within 24 hours

                                                                                                    Your booking request will be confirmed or denied within 24 hours.

                                                                                                      House #1050793vb
                                                                                                      • 3 BR
                                                                                                      • 2 BA
                                                                                                      • 1 HF BA
                                                                                                      • Sleeps 6
                                                                                                      3

                                                                                                      Confirmation within 24 hours

                                                                                                      Your booking request will be confirmed or denied within 24 hours.

                                                                                                      • 1 - 50 of 300+

                                                                                                      Annapolis Vacation Rentals (300+)