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Additional fees apply. Taxes may be added.
    Exceptional! 5/5
    (4 reviews)
    avg/night
    • 3 BR
    • 2 BA
    • Sleeps 6
    House #321313vb
    4
    Viewed 97 times in the last 48 hours
      Exceptional! 5/5
      (14 reviews)
      avg/night
      • 5 BR
      • 3 BA
      • Sleeps 10
      House #425548vb
      14
      Viewed 25 times in the last 48 hours
        Wonderful! 4.9/5
        (9 reviews)
        avg/night
        • 4 BR
        • 3 BA
        • 2 HF BA
        • Sleeps 8
        House #746110vb
        9
        Viewed 34 times in the last 48 hours
          Exceptional! 5/5
          (13 reviews)
          avg/night
          • 4 BR
          • 2 BA
          • 1 HF BA
          • Sleeps 9
          House #602844vb
          13
          Viewed 28 times in the last 48 hours
            Exceptional! 5/5
            (19 reviews)
            avg/night
            • 3 BR
            • 2 BA
            • Sleeps 6
            Bungalow #804815vb
            19
            Viewed 25 times in the last 48 hours
              • 5 BR
              • 4 BA
              • 1 HF BA
              • Sleeps 6
              House #159174
              2
                Wonderful! 4.9/5
                (14 reviews)
                avg/night
                • 3 BR
                • 2 BA
                • Sleeps 6
                House #3554393
                14
                Viewed 13 times in the last 48 hours
                  Exceptional! 5/5
                  (8 reviews)
                  avg/night
                  • 3 BR
                  • 1 BA
                  • Sleeps 6
                  House #694738vb
                  8
                  Viewed 41 times in the last 48 hours
                    avg/night
                    • 4 BR
                    • 4 BA
                    • 1 HF BA
                    • Sleeps 7
                    House #3757374
                    3
                    Viewed 14 times in the last 48 hours
                      Exceptional! 5/5
                      (6 reviews)
                      avg/night
                      • 3 BR
                      • 2 BA
                      • Sleeps 8
                      House #3925407
                      6
                      Viewed 29 times in the last 48 hours
                        avg/night
                        • 3 BR
                        • 2 BA
                        • Sleeps 6
                        House #803084vb
                        1
                        Viewed 15 times in the last 48 hours
                          Excellent! 4.6/5
                          (7 reviews)
                          avg/night
                          • 3 BR
                          • 2 BA
                          • 1 HF BA
                          • Sleeps 8
                          House #3621885
                          7
                          Viewed 18 times in the last 48 hours
                            avg/night
                            • 3 BR
                            • 2 BA
                            • Sleeps 6
                            House #891646vb
                            Viewed 8 times in the last 48 hours
                              Exceptional! 5/5
                              (9 reviews)
                              avg/night
                              • 4 BR
                              • 2 BA
                              • Sleeps 8
                              Farmhouse #3767828
                              9
                              Viewed 24 times in the last 48 hours
                                Exceptional! 5/5
                                (4 reviews)
                                avg/night
                                • 4 BR
                                • 1 BA
                                • Sleeps 8
                                House #3942991
                                4
                                Viewed 10 times in the last 48 hours
                                  avg/night
                                  • 4 BR
                                  • 3 BA
                                  • Sleeps 8
                                  House #485451vb
                                  1
                                  Viewed 19 times in the last 48 hours
                                    Wonderful! 4.9/5
                                    (8 reviews)
                                    avg/night
                                    • 3 BR
                                    • 3 BA
                                    • Sleeps 10
                                    House #305998vb
                                    8
                                    Viewed 17 times in the last 48 hours
                                      Exceptional! 5/5
                                      (5 reviews)
                                      avg/night
                                      • 5 BR
                                      • 2 BA
                                      • Sleeps 12
                                      House #628856vb
                                      5
                                      Viewed 24 times in the last 48 hours
                                        avg/night
                                        • 3 BR
                                        • 2 BA
                                        • 1 HF BA
                                        • Sleeps 6
                                        House #894525vb
                                        Viewed 8 times in the last 48 hours
                                          Exceptional! 5/5
                                          (5 reviews)
                                          avg/night
                                          • 5 BR
                                          • 4 BA
                                          • Sleeps 12
                                          House #344072vb
                                          5
                                          Viewed 12 times in the last 48 hours
                                            • 5 BR
                                            • 3 BA
                                            • Sleeps 10
                                            House #3781403
                                            2
                                            Viewed 36 times in the last 48 hours
                                              Exceptional! 5/5
                                              (8 reviews)
                                              avg/night
                                              • 4 BR
                                              • 2 BA
                                              • Sleeps 10
                                              House #446286vb
                                              8
                                              Viewed 47 times in the last 48 hours
                                                • 3 BR
                                                • 2 BA
                                                • 1 HF BA
                                                • Sleeps 6
                                                House #90560vb
                                                2
                                                Viewed 22 times in the last 48 hours
                                                  Wonderful! 4.8/5
                                                  (6 reviews)
                                                  avg/night
                                                  • 4 BR
                                                  • 2 BA
                                                  • Sleeps 6
                                                  House #363251vb
                                                  6
                                                  Viewed 24 times in the last 48 hours
                                                    Exceptional! 5/5
                                                    (6 reviews)
                                                    avg/night
                                                    • 4 BR
                                                    • 3 BA
                                                    • Sleeps 8
                                                    House #411447vb
                                                    6
                                                    Viewed 18 times in the last 48 hours
                                                      • 3 BR
                                                      • Sleeps 8
                                                      House #470387vb
                                                      2
                                                      Viewed 8 times in the last 48 hours
                                                        Excellent! 4.7/5
                                                        (7 reviews)
                                                        avg/night
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 6
                                                        Cottage #702619vb
                                                        7
                                                        Viewed 8 times in the last 48 hours
                                                          Exceptional! 5/5
                                                          (8 reviews)
                                                          avg/night
                                                          • 5 BR
                                                          • 3 BA
                                                          • 1 HF BA
                                                          • Sleeps 10
                                                          House #716643vb
                                                          8
                                                          Viewed 6 times in the last 48 hours
                                                            avg/night
                                                            • 2 BR
                                                            • 2 BA
                                                            • Sleeps 4
                                                            House #3596889
                                                            Viewed 10 times in the last 48 hours
                                                              • 4 BR
                                                              • 2 BA
                                                              • Sleeps 8
                                                              Cottage #556885vb
                                                              1
                                                                Wonderful! 4.9/5
                                                                (17 reviews)
                                                                avg/night
                                                                • 2 BR
                                                                • 1 BA
                                                                • Sleeps 6
                                                                Cottage #360888vb
                                                                17
                                                                Viewed 10 times in the last 48 hours
                                                                  avg/night
                                                                  • 4 BR
                                                                  • 2 BA
                                                                  • Sleeps 8
                                                                  Cottage #4062137
                                                                  2
                                                                  Viewed 18 times in the last 48 hours
                                                                    avg/night
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 7
                                                                    House #908170vb
                                                                    1
                                                                    Viewed 27 times in the last 48 hours
                                                                      Excellent! 4.7/5
                                                                      (10 reviews)
                                                                      avg/night
                                                                      • 4 BR
                                                                      • 3 BA
                                                                      • Sleeps 10
                                                                      House #476247vb
                                                                      10
                                                                        • 3 BR
                                                                        • 3 BA
                                                                        • Sleeps 6
                                                                        House #885475vb
                                                                          Exceptional! 5/5
                                                                          (4 reviews)
                                                                          avg/night
                                                                          • 4 BR
                                                                          • 3 BA
                                                                          • Sleeps 8
                                                                          House #989574
                                                                          4
                                                                          Viewed 9 times in the last 48 hours
                                                                            • 2 BR
                                                                            • 1 BA
                                                                            • Sleeps 6
                                                                            Cottage #597850vb
                                                                            9
                                                                              • 4 BR
                                                                              • 2 BA
                                                                              • Sleeps 8
                                                                              House #3931482
                                                                              2
                                                                              Viewed 108 times in the last 48 hours
                                                                                • 4 BR
                                                                                • 3 BA
                                                                                • Sleeps 8
                                                                                Chateau / Country House #817980vb
                                                                                3
                                                                                Viewed 16 times in the last 48 hours
                                                                                  • 7 BR
                                                                                  • 4 BA
                                                                                  • Sleeps 15
                                                                                  House #672071vb
                                                                                    • 4 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 5
                                                                                    House #474895vb
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 6
                                                                                      House #965493vb
                                                                                      Viewed 9 times in the last 48 hours
                                                                                        avg/night
                                                                                        • 3 BR
                                                                                        • 3 BA
                                                                                        • Sleeps 7
                                                                                        House #326053
                                                                                        2
                                                                                        Viewed 5 times in the last 48 hours
                                                                                          • 4 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 8
                                                                                          House #857206vb
                                                                                          Viewed 7 times in the last 48 hours
                                                                                            Exceptional! 5/5
                                                                                            (4 reviews)
                                                                                            avg/night
                                                                                            • 3 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 6
                                                                                            House #250830
                                                                                            4
                                                                                            Viewed 9 times in the last 48 hours
                                                                                              • 2 BR
                                                                                              • Sleeps 4
                                                                                              House #593484vb
                                                                                              2
                                                                                              Viewed 12 times in the last 48 hours
                                                                                                • 4 BR
                                                                                                • 3 BA
                                                                                                • Sleeps 6
                                                                                                Chateau / Country House #472283vb
                                                                                                2
                                                                                                  Exceptional! 5/5
                                                                                                  (4 reviews)
                                                                                                  avg/night
                                                                                                  • 3 BR
                                                                                                  • 1 BA
                                                                                                  • 1 HF BA
                                                                                                  • Sleeps 8
                                                                                                  House #292262vb
                                                                                                  4
                                                                                                    Exceptional! 5/5
                                                                                                    (4 reviews)
                                                                                                    avg/night
                                                                                                    • 4 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 10
                                                                                                    House #422449vb
                                                                                                    4
                                                                                                    Viewed 6 times in the last 48 hours
                                                                                                      View details for price
                                                                                                      • 4 BR
                                                                                                      • 3 BA
                                                                                                      • Sleeps 8
                                                                                                      House #829820vb
                                                                                                      • 1 - 50 of 300+

                                                                                                      Shelter Island: Vacation Rentals (1,935)

                                                                                                       

                                                                                                      Recent Shelter Island Reviews

                                                                                                      Incredible summer home

                                                                                                      5 of 5
                                                                                                      This house has it all!! It is on a beautiful, quiet property and has every amenity needed for an incredibly relaxing weekend. I didn't want to leave!! Hosts were so nice and even left us a cute note and a delicious bottle of wine. Would love to come back next summer!!
                                                                                                      • Submitted: Jan 4, 2017
                                                                                                      • Stayed: Jun 2016

                                                                                                      Lovely Victorian Home

                                                                                                      4 of 5
                                                                                                      We recently had the pleasure of staying at the Victorian house in Shelter Island for a wedding in September. After a brief orientation we settled in, choosing bedrooms and spreading out .The house is absolutely charming and right across from the street is the water. The house is spacious indoor as well as outdoors. The beds were very comfortable. The layout of the house was very accommodating for different activities such as watching TV, reading, playing games etc. The Kitchen was very functional and spacious. The house also has s wonderful porch to enjoy the scenery while having coffee. It also has a huge backyard with a patio and grill. It’s an excellent place for families with children because of the fenced in property. There is parking for approximately 5 vehicles. There are some restaurants within walking distance and it’s a wonderful place to go for walks. Convenient to everything we wanted to see and do-including walking distance to the ferry, which made for an easy day trip to Greenpoint, NY and venture out to more restaurants, antique shops, wineries etc. The Wineries were absolutely wonderful! Wifi service was excellent. We would definitely stay here again. THANK YOU!
                                                                                                      • Submitted: Nov 6, 2016
                                                                                                      • Stayed: Sep 2016

                                                                                                      Beautifully curated, relaxing home

                                                                                                      5 of 5
                                                                                                      We had a relaxing stay with our extended family at this beautiful house and property over the summer. We took advantage of the lovely dock everyday with the in-house kayaks, canoe and paddleboard. Preparing meals in the chef's kitchen was a dream. We loved picking books out of the stocked library and enjoying the fresh air from the many sliding glass doors circulating over the designed open floor plan. All in all a fantastic getaway!
                                                                                                      • Submitted: Oct 10, 2016
                                                                                                      • Stayed: Aug 2016