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Use filters to find your perfect holiday home.
Favorite
    Viewed 9 times in the last 48 hours
    avg/night
    (7 nights minimum)
    House #321313vb
    4
    Favorite
      Viewed 10 times in the last 48 hours
      Exceptional! 5/5
      (29 reviews)
      avg/night
      (2 nights minimum)
      Bungalow #804815vb
      29
      Favorite
        Viewed 6 times in the last 48 hours
        Wonderful! 4.9/5
        (18 reviews)
        avg/night
        (2 nights minimum)
        House #694738vb
        18
        Favorite
          Excellent! 4.6/5
          (8 reviews)
          avg/night
          (14 nights minimum)
          House #3621885
          8
          Favorite
            Viewed 22 times in the last 48 hours
            Wonderful! 4.8/5
            (17 reviews)
            avg/night
            (2 nights minimum)
            House #602844vb
            17
            Favorite
              Viewed 14 times in the last 48 hours
              Exceptional! 5/5
              (12 reviews)
              avg/night
              House #352116vb
              12
              Favorite
                avg/night
                (6 - 14 nights minimum)
                House #803084vb
                2
                Favorite
                  Viewed 15 times in the last 48 hours
                  Exceptional! 5/5
                  (9 reviews)
                  avg/night
                  (3 nights minimum)
                  House #446286vb
                  9
                  Favorite
                    Viewed 10 times in the last 48 hours
                    Wonderful! 4.9/5
                    (18 reviews)
                    avg/night
                    (2 nights minimum)
                    House #746110vb
                    18
                    Favorite
                      Viewed 10 times in the last 48 hours
                      svg-lightning
                      avg/night
                      (7 nights minimum)
                      House #894525vb
                      1
                      Favorite
                        Viewed 26 times in the last 48 hours
                        Wonderful! 4.9/5
                        (8 reviews)
                        avg/night
                        (2 nights minimum)
                        House #3925407
                        8
                        Favorite
                          Wonderful! 4.9/5
                          (19 reviews)
                          avg/night
                          (2 - 30 nights minimum)
                          House #3554393
                          19
                          Favorite
                            Viewed 10 times in the last 48 hours
                            avg/night
                            (3 - 7 nights minimum)
                            House #1050826vb
                            2
                            Favorite
                              avg/night
                              (7 nights minimum)
                              House #4522864
                              1
                              Favorite
                                Viewed 20 times in the last 48 hours
                                Exceptional! 5/5
                                (7 reviews)
                                avg/night
                                (2 - 4 nights minimum)
                                House #1116587vb
                                7
                                Favorite
                                  Viewed 6 times in the last 48 hours
                                  avg/night
                                  (7 nights minimum)
                                  House #1015933vb
                                  2
                                  Favorite
                                    Viewed 24 times in the last 48 hours
                                    Exceptional! 5/5
                                    (14 reviews)
                                    avg/night
                                    (3 nights minimum)
                                    House #304851vb
                                    14
                                    Favorite
                                      Wonderful! 4.9/5
                                      (18 reviews)
                                      avg/night
                                      (3 - 14 nights minimum)
                                      Cottage #360888vb
                                      18
                                      Favorite
                                        Viewed 7 times in the last 48 hours
                                        Exceptional! 5/5
                                        (18 reviews)
                                        avg/night
                                        (14 nights minimum)
                                        House #425548vb
                                        18
                                        Favorite
                                          avg/night
                                          (3 - 7 nights minimum)
                                          Cottage #556885vb
                                          2
                                          Favorite
                                            Excellent! 4.7/5
                                            (7 reviews)
                                            avg/night
                                            (14 nights minimum)
                                            Cottage #702619vb
                                            7
                                            Favorite
                                              Viewed 13 times in the last 48 hours
                                              Wonderful! 4.9/5
                                              (8 reviews)
                                              avg/night
                                              (4 - 14 nights minimum)
                                              House #305998vb
                                              8
                                              Favorite
                                                Viewed 5 times in the last 48 hours
                                                Exceptional! 5/5
                                                (6 reviews)
                                                avg/night
                                                (7 nights minimum)
                                                House #628856vb
                                                6
                                                Favorite
                                                  Viewed 19 times in the last 48 hours
                                                  avg/night
                                                  House #4327666
                                                  3
                                                  Favorite
                                                    Viewed 5 times in the last 48 hours
                                                    Exceptional! 5/5
                                                    (7 reviews)
                                                    avg/night
                                                    (4 - 5 nights minimum)
                                                    House #344072vb
                                                    7
                                                    Favorite
                                                      Viewed 9 times in the last 48 hours
                                                      avg/night
                                                      (14 nights minimum)
                                                      House #1073110vb
                                                      2
                                                      Favorite
                                                        avg/night
                                                        (14 nights minimum)
                                                        House #891646vb
                                                        1
                                                        Favorite
                                                          Viewed 5 times in the last 48 hours
                                                          Exceptional! 5/5
                                                          (5 reviews)
                                                          avg/night
                                                          (7 - 14 nights minimum)
                                                          House #412629vb
                                                          5
                                                          Favorite
                                                            Viewed 6 times in the last 48 hours
                                                            avg/night
                                                            (2 - 7 nights minimum)
                                                            House #4154562
                                                            Favorite
                                                              avg/night
                                                              (3 - 30 nights minimum)
                                                              House #1062144vb
                                                              4
                                                              Favorite
                                                                Viewed 22 times in the last 48 hours
                                                                Premier Partner
                                                                Exceptional! 5/5
                                                                (10 reviews)
                                                                svg-lightning
                                                                avg/night
                                                                (2 nights minimum)
                                                                House #4677401
                                                                10
                                                                Favorite
                                                                  Exceptional! 5/5
                                                                  (10 reviews)
                                                                  avg/night
                                                                  (4 nights minimum)
                                                                  House #716643vb
                                                                  10
                                                                  Favorite
                                                                    Exceptional! 5/5
                                                                    (5 reviews)
                                                                    avg/night
                                                                    (7 - 31 nights minimum)
                                                                    House #989574
                                                                    5
                                                                    Favorite
                                                                      Viewed 6 times in the last 48 hours
                                                                      Excellent! 4.6/5
                                                                      (7 reviews)
                                                                      svg-lightning
                                                                      avg/night
                                                                      (6 - 7 nights minimum)
                                                                      House #480215vb
                                                                      7
                                                                      Favorite
                                                                        avg/night
                                                                        (7 nights minimum)
                                                                        House #672071vb
                                                                        Favorite
                                                                          Viewed 9 times in the last 48 hours
                                                                          avg/night
                                                                          (2 nights minimum)
                                                                          House #4269044
                                                                          2
                                                                          Favorite
                                                                            Exceptional! 5/5
                                                                            (5 reviews)
                                                                            avg/night
                                                                            (3 - 7 nights minimum)
                                                                            House #738669vb
                                                                            5
                                                                            Favorite
                                                                              avg/night
                                                                              (6 nights minimum)
                                                                              House #4515640
                                                                              Favorite
                                                                                avg/night
                                                                                (15 nights minimum)
                                                                                House #857206vb
                                                                                1
                                                                                Favorite
                                                                                  avg/night
                                                                                  (4 nights minimum)
                                                                                  Cottage #4499810
                                                                                  1
                                                                                  Favorite
                                                                                    Viewed 6 times in the last 48 hours
                                                                                    avg/night
                                                                                    (2 - 3 nights minimum)
                                                                                    House #631622vb
                                                                                    3
                                                                                    Favorite
                                                                                      Exceptional! 5/5
                                                                                      (10 reviews)
                                                                                      avg/night
                                                                                      (2 - 7 nights minimum)
                                                                                      House #313937vb
                                                                                      10
                                                                                      Favorite
                                                                                        Wonderful! 4.8/5
                                                                                        (6 reviews)
                                                                                        avg/night
                                                                                        (3 nights minimum)
                                                                                        House #118075vb
                                                                                        6
                                                                                        Favorite
                                                                                          avg/night
                                                                                          (30 nights minimum)
                                                                                          House #159174
                                                                                          2
                                                                                          Favorite
                                                                                            avg/night
                                                                                            (7 nights minimum)
                                                                                            House #286069vb
                                                                                            Favorite
                                                                                              avg/night
                                                                                              (14 nights minimum)
                                                                                              House #292262vb
                                                                                              4
                                                                                              Favorite
                                                                                                avg/night
                                                                                                (14 nights minimum)
                                                                                                House #305667vb
                                                                                                Favorite
                                                                                                  avg/night
                                                                                                  (13 nights minimum)
                                                                                                  House #363552
                                                                                                  Favorite
                                                                                                    Exceptional! 5/5
                                                                                                    (1 reviews)
                                                                                                    avg/night
                                                                                                    (13 - 18 nights minimum)
                                                                                                    House #364166
                                                                                                    1
                                                                                                    Favorite
                                                                                                      avg/night
                                                                                                      (14 nights minimum)
                                                                                                      House #348482vb
                                                                                                      1

                                                                                                      Shelter Island Holiday Homes & Cottages (300+)