Verified Review icon check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag pet-dog svg-multiunit
  • Showing 1-50 of 300+
Additional fees apply. Taxes may be added.
  View map Map
    $95
    avg/night
    House #321313vb
    • 3 BR
    • 2 BA
    • Sleeps 6
    4
    Viewed 86 times in the last 48 hours

    Confirmation within 24 hours

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

      House #746110vb
      • 4 BR
      • 3 BA
      • 2 HF BA
      • Sleeps 8
      9
      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 #425548vb
        • 5 BR
        • 3 BA
        • Sleeps 10
        14
        Viewed 23 times in the last 48 hours

        Confirmation within 24 hours

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

          avg/night
          House #602844vb
          • 4 BR
          • 2 BA
          • 1 HF BA
          • Sleeps 9
          13
          Viewed 58 times in the last 48 hours

          Confirmation within 24 hours

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

            Farmhouse #3767828
            • 4 BR
            • 2 BA
            • Sleeps 8
            9
            Viewed 34 times in the last 48 hours

            Confirmation within 24 hours

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

              avg/night
              House #3925407
              • 3 BR
              • 2 BA
              • Sleeps 8
              6
              Viewed 41 times in the last 48 hours

              Confirmation within 24 hours

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

                House #722961vb
                • 4 BR
                • 3 BA
                • 1 HF BA
                • Sleeps 10
                  House #694738vb
                  • 3 BR
                  • 1 BA
                  • Sleeps 6
                  8
                  Viewed 24 times in the last 48 hours

                  Confirmation within 24 hours

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

                    House #352116vb
                    • 4 BR
                    • 3 BA
                    • Sleeps 7
                    10
                    Viewed 9 times in the last 48 hours
                      avg/night
                      House #115762
                      • 5 BR
                      • 3 BA
                      • Sleeps 12
                      1
                      Viewed 6 times in the last 48 hours
                        House #3554393
                        • 3 BR
                        • 2 BA
                        • Sleeps 6
                        14
                        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
                          Bungalow #804815vb
                          • 3 BR
                          • 2 BA
                          • Sleeps 8
                          19
                          Viewed 69 times in the last 48 hours

                          Confirmation within 24 hours

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

                            avg/night
                            House #3621885
                            • 3 BR
                            • 2 BA
                            • 1 HF BA
                            • Sleeps 8
                            7
                            Viewed 13 times in the last 48 hours

                            Confirmation within 24 hours

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

                              avg/night
                              House #3942991
                              • 4 BR
                              • 1 BA
                              • Sleeps 8
                              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
                                House #803084vb
                                • 3 BR
                                • 2 BA
                                • Sleeps 6
                                1
                                Viewed 20 times in the last 48 hours

                                Confirmation within 24 hours

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

                                  avg/night
                                  House #305998vb
                                  • 3 BR
                                  • 3 BA
                                  • Sleeps 10
                                  8
                                  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 #485451vb
                                    • 4 BR
                                    • 3 BA
                                    • Sleeps 8
                                    1
                                    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
                                      House #446286vb
                                      • 4 BR
                                      • 2 BA
                                      • Sleeps 10
                                      8
                                      Viewed 38 times in the last 48 hours

                                      Confirmation within 24 hours

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

                                        House #628856vb
                                        • 5 BR
                                        • 2 BA
                                        • Sleeps 12
                                        5
                                        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 #891646vb
                                          • 3 BR
                                          • 2 BA
                                          • Sleeps 6
                                          Viewed 13 times in the last 48 hours

                                          Confirmation within 24 hours

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

                                            avg/night
                                            Cottage #360888vb
                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 6
                                            17
                                            Viewed 10 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 34 times in the last 48 hours

                                              Confirmation within 24 hours

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

                                                Apartment #830564vb
                                                • 3 BR
                                                • 2 BA
                                                • Sleeps 6
                                                Viewed 44 times in the last 48 hours

                                                Confirmation within 24 hours

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

                                                  House #90560vb
                                                  • 3 BR
                                                  • 2 BA
                                                  • 1 HF BA
                                                  • Sleeps 6
                                                  2
                                                  Viewed 12 times in the last 48 hours

                                                  Confirmation within 24 hours

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

                                                    avg/night
                                                    House #411447vb
                                                    • 4 BR
                                                    • 3 BA
                                                    • Sleeps 8
                                                    6
                                                    Viewed 14 times in the last 48 hours

                                                    Confirmation within 24 hours

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

                                                      House #470387vb
                                                      • 3 BR
                                                      • Sleeps 8
                                                      2
                                                      Viewed 24 times in the last 48 hours

                                                      Confirmation within 24 hours

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

                                                        Cottage #597850vb
                                                        • 2 BR
                                                        • 1 BA
                                                        • Sleeps 6
                                                        9

                                                        Confirmation within 24 hours

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

                                                          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.

                                                            House #3931482
                                                            • 4 BR
                                                            • 2 BA
                                                            • Sleeps 8
                                                            2
                                                            Viewed 42 times in the last 48 hours

                                                            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
                                                              8
                                                              Viewed 13 times in the last 48 hours

                                                              Confirmation within 24 hours

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

                                                                avg/night
                                                                House #344072vb
                                                                • 5 BR
                                                                • 4 BA
                                                                • Sleeps 12
                                                                5
                                                                Viewed 13 times in the last 48 hours

                                                                Confirmation within 24 hours

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

                                                                  avg/night
                                                                  House #676220vb
                                                                  • 3 BR
                                                                  • 2 BA
                                                                  • Sleeps 8
                                                                  1
                                                                  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
                                                                    House #698921vb
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 6
                                                                    1
                                                                    Viewed 12 times in the last 48 hours

                                                                    Confirmation within 24 hours

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

                                                                      House #476247vb
                                                                      • 4 BR
                                                                      • 3 BA
                                                                      • Sleeps 10
                                                                      10

                                                                      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 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 7 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.

                                                                              avg/night
                                                                              House #894525vb
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • 1 HF BA
                                                                              • Sleeps 6
                                                                              Viewed 27 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
                                                                                3
                                                                                Viewed 8 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
                                                                                  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 #908170vb
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 7
                                                                                    1
                                                                                    Viewed 13 times in the last 48 hours

                                                                                    Confirmation within 24 hours

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

                                                                                      avg/night
                                                                                      House #137734vb
                                                                                      • 4 BR
                                                                                      • 3 BA
                                                                                      • 1 HF BA
                                                                                      • Sleeps 8
                                                                                      7
                                                                                      Viewed 22 times in the last 48 hours

                                                                                      Confirmation within 24 hours

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

                                                                                        House #989574
                                                                                        • 4 BR
                                                                                        • 3 BA
                                                                                        • Sleeps 8
                                                                                        4

                                                                                        Confirmation within 24 hours

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

                                                                                          Chateau / Country House #817980vb
                                                                                          • 4 BR
                                                                                          • 3 BA
                                                                                          • Sleeps 8
                                                                                          3
                                                                                          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 #672071vb
                                                                                            • 7 BR
                                                                                            • 4 BA
                                                                                            • Sleeps 15
                                                                                            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 #363251vb
                                                                                              • 4 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 6
                                                                                              6
                                                                                              Viewed 20 times in the last 48 hours

                                                                                              Confirmation within 24 hours

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

                                                                                                avg/night
                                                                                                House #4327666
                                                                                                • 3 BR
                                                                                                • 3 BA
                                                                                                • 2 HF 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 #474895vb
                                                                                                  • 4 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 5

                                                                                                  Confirmation within 24 hours

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

                                                                                                    House #965493vb
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 6
                                                                                                    Viewed 11 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
                                                                                                      Viewed 8 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+)