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 Default Owner Icon
  • Showing 1-50 of 300+
  View map Map
Additional fees apply. Taxes may be added.
    Exceptional! 5/5
    (4 reviews)
    avg/night
    House #321313vb
    • 3 BR
    • 2 BA
    • Sleeps 6
    4
    Viewed 95 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
      (9 reviews)
      avg/night
      House #746110vb
      • 4 BR
      • 3 BA
      • 2 HF 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.

        Exceptional! 5/5
        (14 reviews)
        avg/night
        House #425548vb
        • 5 BR
        • 3 BA
        • Sleeps 10
        14
        Viewed 27 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 #602844vb
          • 4 BR
          • 2 BA
          • 1 HF BA
          • Sleeps 9
          13
          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
            (19 reviews)
            avg/night
            Bungalow #804815vb
            • 3 BR
            • 2 BA
            • Sleeps 6
            19
            Viewed 22 times in the last 48 hours

            Confirmation within 24 hours

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

              House #3554393
              • 3 BR
              • 2 BA
              • Sleeps 6
              14

              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
                Viewed 8 times in the last 48 hours
                  Exceptional! 5/5
                  (8 reviews)
                  avg/night
                  House #694738vb
                  • 3 BR
                  • 1 BA
                  • Sleeps 6
                  8
                  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
                    (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.

                      Exceptional! 5/5
                      (10 reviews)
                      avg/night
                      House #352116vb
                      • 4 BR
                      • 3 BA
                      • Sleeps 7
                      10
                      Viewed 28 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.

                          Excellent! 4.6/5
                          (7 reviews)
                          avg/night
                          House #3621885
                          • 3 BR
                          • 2 BA
                          • 1 HF BA
                          • Sleeps 8
                          7
                          Viewed 18 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 8 times in the last 48 hours

                            Confirmation within 24 hours

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

                              Exceptional! 5/5
                              (9 reviews)
                              avg/night
                              Farmhouse #3767828
                              • 4 BR
                              • 2 BA
                              • Sleeps 8
                              9
                              Viewed 26 times in the last 48 hours

                              Confirmation within 24 hours

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

                                Exceptional! 5/5
                                (4 reviews)
                                avg/night
                                House #3942991
                                • 4 BR
                                • 1 BA
                                • Sleeps 8
                                4
                                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 #485451vb
                                  • 4 BR
                                  • 3 BA
                                  • Sleeps 8
                                  1
                                  Viewed 15 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 17 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 15 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 15 times in the last 48 hours

                                        Confirmation within 24 hours

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

                                          Exceptional! 5/5
                                          (5 reviews)
                                          avg/night
                                          House #344072vb
                                          • 5 BR
                                          • 4 BA
                                          • Sleeps 12
                                          5
                                          Viewed 18 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 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
                                              (8 reviews)
                                              avg/night
                                              House #446286vb
                                              • 4 BR
                                              • 2 BA
                                              • Sleeps 10
                                              8
                                              Viewed 78 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 23 times in the last 48 hours

                                                Confirmation within 24 hours

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

                                                  Wonderful! 4.8/5
                                                  (6 reviews)
                                                  avg/night
                                                  House #363251vb
                                                  • 4 BR
                                                  • 2 BA
                                                  • Sleeps 6
                                                  6
                                                  Viewed 27 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 28 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 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
                                                        (7 reviews)
                                                        avg/night
                                                        Cottage #702619vb
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 6
                                                        7
                                                        Viewed 11 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 #716643vb
                                                          • 5 BR
                                                          • 3 BA
                                                          • 1 HF BA
                                                          • Sleeps 10
                                                          8
                                                          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 #3596889
                                                            • 2 BR
                                                            • 2 BA
                                                            • Sleeps 4
                                                            Viewed 19 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 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 #3757374
                                                                • 4 BR
                                                                • 4 BA
                                                                • 1 HF BA
                                                                • Sleeps 7
                                                                3
                                                                Viewed 15 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
                                                                  Cottage #360888vb
                                                                  • 2 BR
                                                                  • 1 BA
                                                                  • Sleeps 6
                                                                  17
                                                                  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 #4062137
                                                                    • 4 BR
                                                                    • 2 BA
                                                                    • Sleeps 8
                                                                    2
                                                                    Viewed 19 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 19 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

                                                                        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 #4479416
                                                                            • 1 BR
                                                                            • 1 BA
                                                                            • Sleeps 4
                                                                            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 #137734vb
                                                                              • 4 BR
                                                                              • 3 BA
                                                                              • 1 HF BA
                                                                              • Sleeps 8
                                                                              7
                                                                              Viewed 26 times in the last 48 hours

                                                                              Confirmation within 24 hours

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

                                                                                Exceptional! 5/5
                                                                                (4 reviews)
                                                                                avg/night
                                                                                House #989574
                                                                                • 4 BR
                                                                                • 3 BA
                                                                                • Sleeps 8
                                                                                4
                                                                                Viewed 16 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.

                                                                                    House #3931482
                                                                                    • 4 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 8
                                                                                    2
                                                                                    Viewed 83 times in the last 48 hours

                                                                                    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 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 #672071vb
                                                                                        • 7 BR
                                                                                        • 4 BA
                                                                                        • Sleeps 15
                                                                                        Viewed 6 times in the last 48 hours

                                                                                        Confirmation within 24 hours

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

                                                                                          House #4327666
                                                                                          • 3 BR
                                                                                          • 3 BA
                                                                                          • 2 HF BA
                                                                                          • Sleeps 8

                                                                                          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 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 #326053
                                                                                                • 3 BR
                                                                                                • 3 BA
                                                                                                • Sleeps 7
                                                                                                2
                                                                                                Viewed 8 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 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
                                                                                                    (4 reviews)
                                                                                                    avg/night
                                                                                                    House #250830
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 6
                                                                                                    4
                                                                                                    Viewed 15 times in the last 48 hours

                                                                                                    Confirmation within 24 hours

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

                                                                                                      Chateau / Country House #472283vb
                                                                                                      • 4 BR
                                                                                                      • 3 BA
                                                                                                      • Sleeps 6
                                                                                                      2

                                                                                                      Confirmation within 24 hours

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

                                                                                                      • 1 - 50 of 300+

                                                                                                      Shelter Island Vacation Rentals (300+)