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  • Showing 1-50 of 300+
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    Exceptional! 5.0/5
    (14 reviews)
    avg/night
    • 5 BR
    • 3 BA
    • Sleeps 10
    House #425548vb
    14
    Viewed 20 times in the last 48 hours
      • 4 BR
      • 4 BA
      • 1 HF BA
      • Sleeps 10
      House #4154990
      3
      Viewed 11 times in the last 48 hours
        $95
        avg/night
        • 3 BR
        • 2 BA
        • Sleeps 6
        House #321313vb
        2
        Viewed 43 times in the last 48 hours
          • 5 BR
          • 4 BA
          • 1 HF BA
          • Sleeps 6
          House #159174
          2
            • 4 BR
            • 3 BA
            • 1 HF BA
            • Sleeps 10
            House #722961vb
            0
            Viewed 5 times in the last 48 hours
              • 6 BR
              • 4 BA
              • 2 HF BA
              • Sleeps 12
              House #3674314
              0
                • 4 BR
                • 4 BA
                • 1 HF BA
                • Sleeps 7
                House #3757374
                3
                  Exceptional! 5.0/5
                  (10 reviews)
                  avg/night
                  • 4 BR
                  • 3 BA
                  • Sleeps 7
                  House #352116vb
                  10
                  Viewed 5 times in the last 48 hours
                    • 5 BR
                    • 3 BA
                    • Sleeps 12
                    House #115762
                    1
                      Exceptional! 5.0/5
                      (8 reviews)
                      avg/night
                      • 3 BR
                      • 1 BA
                      • Sleeps 6
                      House #694738vb
                      8
                      Viewed 43 times in the last 48 hours
                        Wonderful! 4.9/5
                        (14 reviews)
                        avg/night
                        • 3 BR
                        • 2 BA
                        • Sleeps 5
                        House #3554393
                        14
                        Viewed 15 times in the last 48 hours
                          avg/night
                          • 3 BR
                          • 3 BA
                          • Sleeps 7
                          House #326053
                          2
                          Viewed 7 times in the last 48 hours
                            Exceptional! 5.0/5
                            (13 reviews)
                            avg/night
                            • 4 BR
                            • 2 BA
                            • 1 HF BA
                            • Sleeps 9
                            House #602844vb
                            13
                            Viewed 48 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 43 times in the last 48 hours
                                avg/night
                                • 3 BR
                                • 2 BA
                                • Sleeps 6
                                House #891646vb
                                0
                                Viewed 6 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 25 times in the last 48 hours
                                    • 4 BR
                                    • 2 BA
                                    • Sleeps 8
                                    House #3931482
                                    2
                                    Viewed 20 times in the last 48 hours
                                      Exceptional! 5.0/5
                                      (6 reviews)
                                      avg/night
                                      • 3 BR
                                      • 1 BA
                                      • Sleeps 8
                                      House #3925407
                                      6
                                      Viewed 63 times in the last 48 hours
                                        avg/night
                                        • 4 BR
                                        • 1 BA
                                        • Sleeps 8
                                        House #3942991
                                        4
                                        Viewed 24 times in the last 48 hours
                                          avg/night
                                          • 3 BR
                                          • 2 BA
                                          • Sleeps 7
                                          House #908170vb
                                          1
                                          Viewed 9 times in the last 48 hours
                                            • 4 BR
                                            • 3 BA
                                            • Sleeps 8
                                            House #989574
                                            4
                                              • 3 BR
                                              • Sleeps 8
                                              House #470387vb
                                              2
                                              Viewed 20 times in the last 48 hours
                                                Exceptional! 5.0/5
                                                (5 reviews)
                                                avg/night
                                                • 5 BR
                                                • 4 BA
                                                • Sleeps 12
                                                House #344072vb
                                                5
                                                Viewed 20 times in the last 48 hours
                                                  avg/night
                                                  • 3 BR
                                                  • 2 BA
                                                  • Sleeps 6
                                                  House #803084vb
                                                  1
                                                  Viewed 19 times in the last 48 hours
                                                    avg/night
                                                    • 3 BR
                                                    • 2 BA
                                                    • Sleeps 6
                                                    House #698921vb
                                                    1
                                                    Viewed 9 times in the last 48 hours
                                                      • 4 BR
                                                      • 2 BA
                                                      • Sleeps 5
                                                      House #474895vb
                                                      0
                                                        Exceptional! 5.0/5
                                                        (5 reviews)
                                                        avg/night
                                                        • 5 BR
                                                        • 2 BA
                                                        • Sleeps 12
                                                        House #628856vb
                                                        5
                                                        Viewed 30 times in the last 48 hours
                                                          Excellent! 4.7/5
                                                          (10 reviews)
                                                          avg/night
                                                          • 4 BR
                                                          • 3 BA
                                                          • Sleeps 10
                                                          House #476247vb
                                                          10
                                                            Exceptional! 5.0/5
                                                            (5 reviews)
                                                            avg/night
                                                            • 2 BR
                                                            • 1 BA
                                                            • Sleeps 4
                                                            House #3684564
                                                            5
                                                              Exceptional! 5.0/5
                                                              (6 reviews)
                                                              avg/night
                                                              • 4 BR
                                                              • 3 BA
                                                              • Sleeps 8
                                                              House #411447vb
                                                              6
                                                              Viewed 19 times in the last 48 hours
                                                                Exceptional! 5.0/5
                                                                (8 reviews)
                                                                avg/night
                                                                • 5 BR
                                                                • 3 BA
                                                                • 1 HF BA
                                                                • Sleeps 10
                                                                House #716643vb
                                                                8
                                                                Viewed 15 times in the last 48 hours
                                                                  avg/night
                                                                  • 3 BR
                                                                  • 3 BA
                                                                  • 2 HF BA
                                                                  • Sleeps 8
                                                                  House #4327666
                                                                  0
                                                                  Viewed 7 times in the last 48 hours
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 8
                                                                    House #676220vb
                                                                    1
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • 1 HF BA
                                                                      • Sleeps 6
                                                                      House #90560vb
                                                                      2
                                                                        Wonderful! 4.9/5
                                                                        (8 reviews)
                                                                        avg/night
                                                                        • 3 BR
                                                                        • 3 BA
                                                                        • Sleeps 10
                                                                        House #305998vb
                                                                        8
                                                                        Viewed 26 times in the last 48 hours
                                                                          avg/night
                                                                          • 2 BR
                                                                          • 2 BA
                                                                          • Sleeps 4
                                                                          House #3596889
                                                                          0
                                                                          Viewed 10 times in the last 48 hours
                                                                            Excellent! 4.6/5
                                                                            (7 reviews)
                                                                            avg/night
                                                                            • 4 BR
                                                                            • 3 BA
                                                                            • 1 HF BA
                                                                            • Sleeps 8
                                                                            House #137734vb
                                                                            7
                                                                            Viewed 11 times in the last 48 hours
                                                                              • 4 BR
                                                                              • 2 BA
                                                                              • Sleeps 8
                                                                              House #857206vb
                                                                              0
                                                                              Viewed 10 times in the last 48 hours
                                                                                Excellent! 4.6/5
                                                                                (5 reviews)
                                                                                avg/night
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Sleeps 7
                                                                                House #338964vb
                                                                                5
                                                                                Viewed 12 times in the last 48 hours
                                                                                  Wonderful! 4.8/5
                                                                                  (6 reviews)
                                                                                  avg/night
                                                                                  • 4 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                  House #363251vb
                                                                                  6
                                                                                  Viewed 36 times in the last 48 hours
                                                                                    • 4 BR
                                                                                    • 3 BA
                                                                                    • Sleeps 10
                                                                                    House #422449vb
                                                                                    4
                                                                                      Exceptional! 5.0/5
                                                                                      (8 reviews)
                                                                                      avg/night
                                                                                      • 4 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 10
                                                                                      House #446286vb
                                                                                      8
                                                                                      Viewed 87 times in the last 48 hours
                                                                                        View details for price
                                                                                        • 4 BR
                                                                                        • 3 BA
                                                                                        • Sleeps 8
                                                                                        House #829820vb
                                                                                        0
                                                                                          • 5 BR
                                                                                          • 3 BA
                                                                                          • Sleeps 10
                                                                                          House #3781403
                                                                                          2
                                                                                          Viewed 22 times in the last 48 hours
                                                                                            • 3 BR
                                                                                            • 3 BA
                                                                                            • Sleeps 6
                                                                                            House #885475vb
                                                                                            0
                                                                                              • 3 BR
                                                                                              • 2 BA
                                                                                              • 1 HF BA
                                                                                              • Sleeps 10
                                                                                              House #725584vb
                                                                                              0
                                                                                                $93
                                                                                                avg/night
                                                                                                • 3 BR
                                                                                                • 2 BA
                                                                                                • 1 HF BA
                                                                                                • Sleeps 6
                                                                                                House #894525vb
                                                                                                0
                                                                                                Viewed 11 times in the last 48 hours
                                                                                                  • 3 BR
                                                                                                  • 3 BA
                                                                                                  • Sleeps 7
                                                                                                  House #611940vb
                                                                                                  1
                                                                                                    • 3 BR
                                                                                                    • 4 BA
                                                                                                    • Sleeps 6
                                                                                                    House #470694vb
                                                                                                    0
                                                                                                      • 3 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 8
                                                                                                      House #3783208
                                                                                                      0
                                                                                                      • 1 - 50 of 300+

                                                                                                      Shelter Island: House Rentals (1,888)

                                                                                                       

                                                                                                      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