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    avg/night
    House #321313vb
    • 3 BR
    • 2 BA
    • Sleeps 6
    4
    Viewed 104 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 33 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 42 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 #694738vb
          • 3 BR
          • 1 BA
          • Sleeps 6
          13
          Viewed 16 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
            Bungalow #804815vb
            • 3 BR
            • 2 BA
            • Sleeps 6
            22
            Viewed 56 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
              (17 reviews)
              avg/night
              House #3554393
              • 3 BR
              • 2 BA
              • Sleeps 6
              17
              Viewed 15 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.

                  avg/night
                  House #803084vb
                  • 3 BR
                  • 2 BA
                  • Sleeps 6
                  2
                  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
                    (13 reviews)
                    avg/night
                    House #746110vb
                    • 4 BR
                    • 3 BA
                    • 2 HF BA
                    • Sleeps 8
                    13
                    Viewed 15 times in the last 48 hours

                    Confirmation within 24 hours

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

                      House #891646vb
                      • 3 BR
                      • 2 BA
                      • Sleeps 6
                      1

                      Confirmation within 24 hours

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

                        Excellent! 4.7/5
                        (11 reviews)
                        avg/night
                        House #476247vb
                        • 4 BR
                        • 3 BA
                        • Sleeps 10
                        11
                        Viewed 35 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 24 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 8 times in the last 48 hours

                            Instant confirmation

                            Your booking request will be confirmed immediately.

                              Exceptional! 5/5
                              (12 reviews)
                              avg/night
                              Farmhouse #3767828
                              • 4 BR
                              • 2 BA
                              • Sleeps 10
                              12
                              Viewed 27 times in the last 48 hours

                              Instant confirmation

                              Your booking request will be confirmed immediately.

                                Exceptional! 5/5
                                (7 reviews)
                                View details for price
                                House #3594708
                                • 3 BR
                                • 3 BA
                                • Sleeps 6
                                7
                                Viewed 15 times in the last 48 hours

                                Confirmation within 24 hours

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

                                  View details for price
                                  House #3781403
                                  • 5 BR
                                  • 3 BA
                                  • Sleeps 10
                                  2
                                  Viewed 10 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 16 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 46 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
                                        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
                                          (14 reviews)
                                          avg/night
                                          House #425548vb
                                          • 4 BR
                                          • 3 BA
                                          • Sleeps 10
                                          14
                                          Viewed 7 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 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
                                              (18 reviews)
                                              avg/night
                                              Cottage #360888vb
                                              • 2 BR
                                              • 1 BA
                                              • Sleeps 6
                                              18
                                              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
                                                House #4522864
                                                • 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.

                                                  avg/night
                                                  Cottage #556885vb
                                                  • 4 BR
                                                  • 2 BA
                                                  • Sleeps 8
                                                  1
                                                  Viewed 18 times in the last 48 hours

                                                  Confirmation within 24 hours

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

                                                    House #1050826vb
                                                    • 4 BR
                                                    • 3 BA
                                                    • 1 HF BA
                                                    • Sleeps 10
                                                    1
                                                    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
                                                      (5 reviews)
                                                      avg/night
                                                      House #628856vb
                                                      • 5 BR
                                                      • 2 BA
                                                      • Sleeps 12
                                                      5
                                                      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
                                                        (8 reviews)
                                                        avg/night
                                                        House #305998vb
                                                        • 3 BR
                                                        • 3 BA
                                                        • Sleeps 10
                                                        8
                                                        Viewed 22 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 28 times in the last 48 hours

                                                          Confirmation within 24 hours

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

                                                            House #1073110vb
                                                            • 3 BR
                                                            • 2 BA
                                                            • Sleeps 5

                                                            Confirmation within 24 hours

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

                                                              avg/night
                                                              House #412629vb
                                                              • 5 BR
                                                              • 3 BA
                                                              • Sleeps 9
                                                              4
                                                              Viewed 17 times in the last 48 hours

                                                              Confirmation within 24 hours

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

                                                                avg/night
                                                                Farmhouse #683544vb
                                                                • 5 BR
                                                                • 3 BA
                                                                • 1 HF BA
                                                                • Sleeps 9
                                                                2
                                                                Viewed 5 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 6 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.

                                                                      $66
                                                                      avg/night
                                                                      Cottage #4479416
                                                                      • 1 BR
                                                                      • 1 BA
                                                                      • Sleeps 4
                                                                      1
                                                                      Viewed 9 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.

                                                                          avg/night
                                                                          Cottage #4499810
                                                                          • 3 BR
                                                                          • 1 BA
                                                                          • Sleeps 6
                                                                          Viewed 7 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 #352116vb
                                                                            • 4 BR
                                                                            • 3 BA
                                                                            • Sleeps 7
                                                                            10
                                                                            Viewed 55 times in the last 48 hours

                                                                            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 7 times in the last 48 hours

                                                                              Instant confirmation

                                                                              Your booking request will be confirmed immediately.

                                                                                avg/night
                                                                                House #4269044
                                                                                • 2 BR
                                                                                • 1 BA
                                                                                • Sleeps 6
                                                                                1
                                                                                Viewed 18 times in the last 48 hours

                                                                                Confirmation within 24 hours

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

                                                                                  House #4570385
                                                                                  • 3 BR
                                                                                  • 1 HF BA
                                                                                  • Sleeps 6

                                                                                  Confirmation within 24 hours

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

                                                                                    House #4515640
                                                                                    • 5 BR
                                                                                    • 4 BA
                                                                                    • Sleeps 8

                                                                                    Confirmation within 24 hours

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

                                                                                      House #250830
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 6
                                                                                      4

                                                                                      Confirmation within 24 hours

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

                                                                                        House #716643vb
                                                                                        • 5 BR
                                                                                        • 3 BA
                                                                                        • 1 HF BA
                                                                                        • Sleeps 10
                                                                                        10

                                                                                        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.

                                                                                            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 39 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

                                                                                                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 9 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.

                                                                                                      House #292262vb
                                                                                                      • 3 BR
                                                                                                      • 1 BA
                                                                                                      • 1 HF BA
                                                                                                      • Sleeps 6
                                                                                                      4

                                                                                                      Confirmation within 24 hours

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

                                                                                                      • 1 - 50 of 300+

                                                                                                      Shelter Island Vacation Rentals (300+)