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    avg/night
    House #321313vb
    • 3 BR
    • 2 BA
    • Sleeps 6
    4
    Viewed 118 times in the last 48 hours

    Confirmation within 24 hours

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

      Exceptional! 5/5
      (14 reviews)
      avg/night
      House #425548vb
      • 4 BR
      • 3 BA
      • Sleeps 10
      14
      Viewed 20 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
        (15 reviews)
        avg/night
        House #602844vb
        • 4 BR
        • 2 BA
        • 1 HF BA
        • Sleeps 9
        15
        Viewed 33 times in the last 48 hours

        Confirmation within 24 hours

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

          Exceptional! 5/5
          (12 reviews)
          avg/night
          House #694738vb
          • 3 BR
          • 1 BA
          • Sleeps 6
          12
          Viewed 36 times in the last 48 hours

          Confirmation within 24 hours

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

            Exceptional! 5/5
            (8 reviews)
            avg/night
            House #446286vb
            • 4 BR
            • 2 BA
            • Sleeps 10
            8
            Viewed 25 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
              (16 reviews)
              avg/night
              House #3554393
              • 3 BR
              • 2 BA
              • Sleeps 6
              16
              Viewed 22 times in the last 48 hours

              Confirmation within 24 hours

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

                Excellent! 4.6/5
                (7 reviews)
                avg/night
                House #3621885
                • 3 BR
                • 2 BA
                • 1 HF BA
                • Sleeps 6
                7
                Viewed 5 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
                  (11 reviews)
                  avg/night
                  House #746110vb
                  • 4 BR
                  • 3 BA
                  • 2 HF BA
                  • Sleeps 8
                  11
                  Viewed 16 times in the last 48 hours

                  Confirmation within 24 hours

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

                    avg/night
                    House #803084vb
                    • 3 BR
                    • 2 BA
                    • Sleeps 6
                    1
                    Viewed 11 times in the last 48 hours

                    Confirmation within 24 hours

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

                      avg/night
                      House #891646vb
                      • 3 BR
                      • 2 BA
                      • Sleeps 6
                      Viewed 5 times in the last 48 hours

                      Confirmation within 24 hours

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

                        Exceptional! 5/5
                        (6 reviews)
                        avg/night
                        House #3925407
                        • 3 BR
                        • 2 BA
                        • Sleeps 8
                        6
                        Viewed 29 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
                          (7 reviews)
                          avg/night
                          Cottage #702619vb
                          • 3 BR
                          • 2 BA
                          • Sleeps 6
                          7
                          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
                            (20 reviews)
                            avg/night
                            Bungalow #804815vb
                            • 3 BR
                            • 2 BA
                            • Sleeps 6
                            20
                            Viewed 103 times in the last 48 hours

                            Confirmation within 24 hours

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

                              avg/night
                              House #894525vb
                              • 3 BR
                              • 2 BA
                              • 1 HF BA
                              • Sleeps 6
                              Viewed 6 times in the last 48 hours

                              Instant confirmation

                              Your booking request will be confirmed immediately.

                                Exceptional! 5/5
                                (5 reviews)
                                avg/night
                                House #485451vb
                                • 4 BR
                                • 3 BA
                                • Sleeps 8
                                5
                                Viewed 13 times in the last 48 hours

                                Confirmation within 24 hours

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

                                  House #3781403
                                  • 5 BR
                                  • 3 BA
                                  • Sleeps 10
                                  2
                                  Viewed 14 times in the last 48 hours

                                  Confirmation within 24 hours

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

                                    Exceptional! 5/5
                                    (5 reviews)
                                    avg/night
                                    House #628856vb
                                    • 5 BR
                                    • 2 BA
                                    • Sleeps 12
                                    5
                                    Viewed 12 times in the last 48 hours

                                    Confirmation within 24 hours

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

                                      Exceptional! 5/5
                                      (6 reviews)
                                      avg/night
                                      House #411447vb
                                      • 4 BR
                                      • 3 BA
                                      • Sleeps 8
                                      6

                                      Confirmation within 24 hours

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

                                        Exceptional! 5/5
                                        (7 reviews)
                                        avg/night
                                        House #3594708
                                        • 3 BR
                                        • 3 BA
                                        • Sleeps 6
                                        7
                                        Viewed 20 times in the last 48 hours

                                        Confirmation within 24 hours

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

                                          Exceptional! 5/5
                                          (6 reviews)
                                          avg/night
                                          House #344072vb
                                          • 5 BR
                                          • 4 BA
                                          • Sleeps 12
                                          6
                                          Viewed 14 times in the last 48 hours

                                          Confirmation within 24 hours

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

                                            Exceptional! 5/5
                                            (13 reviews)
                                            avg/night
                                            House #304851vb
                                            • 3 BR
                                            • 3 BA
                                            • 1 HF BA
                                            • Sleeps 6
                                            13
                                            Viewed 10 times in the last 48 hours

                                            Confirmation within 24 hours

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

                                              avg/night
                                              House #3596889
                                              • 2 BR
                                              • 2 BA
                                              • Sleeps 4
                                              Viewed 16 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
                                                (18 reviews)
                                                avg/night
                                                Cottage #360888vb
                                                • 2 BR
                                                • 1 BA
                                                • Sleeps 6
                                                18
                                                Viewed 8 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
                                                  (10 reviews)
                                                  avg/night
                                                  House #476247vb
                                                  • 4 BR
                                                  • 3 BA
                                                  • Sleeps 10
                                                  10
                                                  Viewed 71 times in the last 48 hours

                                                  Confirmation within 24 hours

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

                                                    Exceptional! 5/5
                                                    (10 reviews)
                                                    avg/night
                                                    Farmhouse #3767828
                                                    • 4 BR
                                                    • 2 BA
                                                    • Sleeps 8
                                                    10
                                                    Viewed 39 times in the last 48 hours

                                                    Instant confirmation

                                                    Your booking request will be confirmed immediately.

                                                      House #1050826vb
                                                      • 4 BR
                                                      • 3 BA
                                                      • 1 HF BA
                                                      • Sleeps 10
                                                      Viewed 10 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
                                                        (8 reviews)
                                                        avg/night
                                                        House #305998vb
                                                        • 3 BR
                                                        • 3 BA
                                                        • Sleeps 10
                                                        8
                                                        Viewed 19 times in the last 48 hours

                                                        Confirmation within 24 hours

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

                                                          Cottage #556885vb
                                                          • 4 BR
                                                          • 2 BA
                                                          • Sleeps 8
                                                          1

                                                          Confirmation within 24 hours

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

                                                            Farmhouse #683544vb
                                                            • 5 BR
                                                            • 3 BA
                                                            • 1 HF BA
                                                            • Sleeps 9
                                                            2

                                                            Confirmation within 24 hours

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

                                                              avg/night
                                                              House #1073110vb
                                                              • 3 BR
                                                              • 2 BA
                                                              • Sleeps 5
                                                              Viewed 14 times in the last 48 hours

                                                              Confirmation within 24 hours

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

                                                                avg/night
                                                                House #3757374
                                                                • 4 BR
                                                                • 4 BA
                                                                • 1 HF BA
                                                                • Sleeps 7
                                                                4
                                                                Viewed 8 times in the last 48 hours

                                                                Confirmation within 24 hours

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

                                                                  avg/night
                                                                  Cottage #4479416
                                                                  • 1 BR
                                                                  • 1 BA
                                                                  • Sleeps 4
                                                                  Viewed 7 times in the last 48 hours

                                                                  Confirmation within 24 hours

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

                                                                    House #885475vb
                                                                    • 3 BR
                                                                    • 3 BA
                                                                    • Sleeps 6

                                                                    Confirmation within 24 hours

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

                                                                      Excellent! 4.5/5
                                                                      (6 reviews)
                                                                      avg/night
                                                                      House #480215vb
                                                                      • 5 BR
                                                                      • 3 BA
                                                                      • Sleeps 12
                                                                      6
                                                                      Viewed 20 times in the last 48 hours

                                                                      Instant confirmation

                                                                      Your booking request will be confirmed immediately.

                                                                        avg/night
                                                                        House #3942991
                                                                        • 4 BR
                                                                        • 1 BA
                                                                        • Sleeps 8
                                                                        4
                                                                        Viewed 9 times in the last 48 hours

                                                                        Confirmation within 24 hours

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

                                                                          avg/night
                                                                          House #1015933vb
                                                                          • 5 BR
                                                                          • 4 BA
                                                                          • Sleeps 10
                                                                          Viewed 27 times in the last 48 hours

                                                                          Confirmation within 24 hours

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

                                                                            House #4515640
                                                                            • 5 BR
                                                                            • 4 BA
                                                                            • Sleeps 8
                                                                            Viewed 8 times in the last 48 hours

                                                                            Confirmation within 24 hours

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

                                                                              House #4522864
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 6

                                                                              Confirmation within 24 hours

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

                                                                                House #250830
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Sleeps 6
                                                                                4
                                                                                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
                                                                                  (10 reviews)
                                                                                  avg/night
                                                                                  House #716643vb
                                                                                  • 5 BR
                                                                                  • 3 BA
                                                                                  • 1 HF BA
                                                                                  • Sleeps 10
                                                                                  10
                                                                                  Viewed 17 times in the last 48 hours

                                                                                  Confirmation within 24 hours

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

                                                                                    House #857206vb
                                                                                    • 4 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 8
                                                                                    1

                                                                                    Confirmation within 24 hours

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

                                                                                      avg/night
                                                                                      House #4269044
                                                                                      • 2 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 6
                                                                                      1
                                                                                      Viewed 63 times in the last 48 hours

                                                                                      Confirmation within 24 hours

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

                                                                                        avg/night
                                                                                        Cottage #4499810
                                                                                        • 3 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 6
                                                                                        Viewed 32 times in the last 48 hours

                                                                                        Confirmation within 24 hours

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

                                                                                          House #326053
                                                                                          • 3 BR
                                                                                          • 3 BA
                                                                                          • Sleeps 7
                                                                                          3

                                                                                          Confirmation within 24 hours

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

                                                                                            avg/night
                                                                                            House #631622vb
                                                                                            • 3 BR
                                                                                            • 4 BA
                                                                                            • Sleeps 8
                                                                                            3
                                                                                            Viewed 42 times in the last 48 hours

                                                                                            Confirmation within 24 hours

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

                                                                                              House #3931482
                                                                                              • 4 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 8
                                                                                              2
                                                                                              Viewed 7 times in the last 48 hours

                                                                                              Confirmation within 24 hours

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

                                                                                                avg/night
                                                                                                Cottage #4062137
                                                                                                • 4 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 8
                                                                                                2
                                                                                                Viewed 15 times in the last 48 hours

                                                                                                Confirmation within 24 hours

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

                                                                                                  House #965493vb
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 6

                                                                                                  Confirmation within 24 hours

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

                                                                                                    Exceptional! 5/5
                                                                                                    (7 reviews)
                                                                                                    avg/night
                                                                                                    House #553290vb
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 6
                                                                                                    7
                                                                                                    Viewed 10 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
                                                                                                      (6 reviews)
                                                                                                      avg/night
                                                                                                      House #118075vb
                                                                                                      • 3 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 6
                                                                                                      6
                                                                                                      Viewed 30 times in the last 48 hours

                                                                                                      Confirmation within 24 hours

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

                                                                                                      • 1 - 50 of 300+

                                                                                                      Shelter Island Vacation Rentals (300+)