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  • Showing 1-50 of 300+
Additional fees apply. Taxes may be added.
    avg/night
    • 3 BR
    • 2 BA
    • Sleeps 6
    House #321313vb
    4
    Viewed 63 times in the last 48 hours
      Exceptional! 5.0/5
      (14 reviews)
      avg/night
      • 5 BR
      • 3 BA
      • Sleeps 10
      House #425548vb
      14
      Viewed 38 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 37 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 14 times in the last 48 hours
            • 5 BR
            • 4 BA
            • 1 HF BA
            • Sleeps 6
            House #159174
            2
              Exceptional! 5.0/5
              (19 reviews)
              avg/night
              • 3 BR
              • 2 BA
              • Sleeps 8
              Bungalow #804815vb
              19
              Viewed 38 times in the last 48 hours
                Exceptional! 5.0/5
                (6 reviews)
                avg/night
                • 3 BR
                • 1 BA
                • Sleeps 8
                House #3925407
                6
                Viewed 91 times in the last 48 hours
                  avg/night
                  • 4 BR
                  • 4 BA
                  • 1 HF BA
                  • Sleeps 7
                  House #3757374
                  3
                  Viewed 11 times in the last 48 hours
                    Exceptional! 5.0/5
                    (8 reviews)
                    avg/night
                    • 3 BR
                    • 1 BA
                    • Sleeps 6
                    House #694738vb
                    8
                    Viewed 37 times in the last 48 hours
                      Wonderful! 4.9/5
                      (14 reviews)
                      avg/night
                      • 3 BR
                      • 2 BA
                      • Sleeps 5
                      House #3554393
                      14
                      Viewed 7 times in the last 48 hours
                        • 3 BR
                        • 3 BA
                        • Sleeps 7
                        House #326053
                        2
                          Excellent! 4.6/5
                          (7 reviews)
                          avg/night
                          • 3 BR
                          • 2 BA
                          • 1 HF BA
                          • Sleeps 8
                          House #3621885
                          7
                          Viewed 12 times in the last 48 hours
                            avg/night
                            • 3 BR
                            • 2 BA
                            • Sleeps 6
                            House #803084vb
                            1
                            Viewed 22 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! 5.0/5
                                (8 reviews)
                                avg/night
                                • 4 BR
                                • 2 BA
                                • Sleeps 10
                                House #446286vb
                                8
                                Viewed 33 times in the last 48 hours
                                  avg/night
                                  • 3 BR
                                  • 2 BA
                                  • Sleeps 6
                                  House #891646vb
                                  Viewed 13 times in the last 48 hours
                                    • 5 BR
                                    • 3 BA
                                    • Sleeps 10
                                    House #3781403
                                    2
                                    Viewed 17 times in the last 48 hours
                                      • 3 BR
                                      • 2 BA
                                      • Sleeps 6
                                      Apartment #830564vb
                                      Viewed 16 times in the last 48 hours
                                        • 3 BR
                                        • 2 BA
                                        • 1 HF BA
                                        • Sleeps 6
                                        House #90560vb
                                        2
                                        Viewed 5 times in the last 48 hours
                                          • 3 BR
                                          • Sleeps 8
                                          House #470387vb
                                          2
                                          Viewed 7 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 17 times in the last 48 hours
                                                avg/night
                                                • 4 BR
                                                • 1 BA
                                                • Sleeps 8
                                                House #3942991
                                                4
                                                Viewed 23 times in the last 48 hours
                                                  Exceptional! 5.0/5
                                                  (5 reviews)
                                                  avg/night
                                                  • 5 BR
                                                  • 4 BA
                                                  • Sleeps 12
                                                  House #344072vb
                                                  5
                                                  Viewed 22 times in the last 48 hours
                                                    • 3 BR
                                                    • 2 BA
                                                    • Sleeps 8
                                                    House #676220vb
                                                    1
                                                      avg/night
                                                      • 3 BR
                                                      • 2 BA
                                                      • Sleeps 6
                                                      House #698921vb
                                                      1
                                                      Viewed 9 times in the last 48 hours
                                                        Excellent! 4.7/5
                                                        (7 reviews)
                                                        avg/night
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 6
                                                        Cottage #702619vb
                                                        7
                                                        Viewed 7 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 6 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
                                                              • 5 BR
                                                              • 2 BA
                                                              • Sleeps 12
                                                              House #628856vb
                                                              5
                                                              Viewed 10 times in the last 48 hours
                                                                avg/night
                                                                • 2 BR
                                                                • 2 BA
                                                                • Sleeps 4
                                                                House #3596889
                                                                Viewed 15 times in the last 48 hours
                                                                  • 3 BR
                                                                  • 3 BA
                                                                  • Sleeps 6
                                                                  House #885475vb
                                                                    avg/night
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 7
                                                                    House #908170vb
                                                                    1
                                                                    Viewed 9 times in the last 48 hours
                                                                      Exceptional! 5.0/5
                                                                      (6 reviews)
                                                                      avg/night
                                                                      • 4 BR
                                                                      • 3 BA
                                                                      • Sleeps 8
                                                                      House #411447vb
                                                                      6
                                                                      Viewed 18 times in the last 48 hours
                                                                        • 4 BR
                                                                        • 3 BA
                                                                        • Sleeps 8
                                                                        House #989574
                                                                        4
                                                                          avg/night
                                                                          • 4 BR
                                                                          • 2 BA
                                                                          • Sleeps 8
                                                                          Cottage #4062137
                                                                          2
                                                                          Viewed 19 times in the last 48 hours
                                                                            avg/night
                                                                            • 7 BR
                                                                            • 4 BA
                                                                            • Sleeps 15
                                                                            House #672071vb
                                                                            Viewed 14 times in the last 48 hours
                                                                              Wonderful! 4.8/5
                                                                              (6 reviews)
                                                                              avg/night
                                                                              • 4 BR
                                                                              • 2 BA
                                                                              • Sleeps 6
                                                                              House #363251vb
                                                                              6
                                                                              Viewed 32 times in the last 48 hours
                                                                                avg/night
                                                                                • 4 BR
                                                                                • 2 BA
                                                                                • Sleeps 8
                                                                                Cottage #556885vb
                                                                                1
                                                                                Viewed 7 times in the last 48 hours
                                                                                  • 4 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 5
                                                                                  House #474895vb
                                                                                    Exceptional! 5.0/5
                                                                                    (5 reviews)
                                                                                    avg/night
                                                                                    • 2 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 4
                                                                                    House #3684564
                                                                                    5
                                                                                      • 4 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 8
                                                                                      House #857206vb
                                                                                        Excellent! 4.6/5
                                                                                        (5 reviews)
                                                                                        avg/night
                                                                                        • 3 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 7
                                                                                        House #338964vb
                                                                                        5
                                                                                        Viewed 13 times in the last 48 hours
                                                                                          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
                                                                                              • 4 BR
                                                                                              • 3 BA
                                                                                              • Sleeps 7
                                                                                              Chateau / Country House #4202867
                                                                                              1
                                                                                                avg/night
                                                                                                • 4 BR
                                                                                                • 3 BA
                                                                                                • Sleeps 6
                                                                                                Chateau / Country House #472283vb
                                                                                                2
                                                                                                Viewed 5 times in the last 48 hours
                                                                                                  • 4 BR
                                                                                                  • 3 BA
                                                                                                  • Sleeps 8
                                                                                                  Chateau / Country House #817980vb
                                                                                                    $93
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • 1 HF BA
                                                                                                    • Sleeps 6
                                                                                                    House #894525vb
                                                                                                    Viewed 24 times in the last 48 hours
                                                                                                      • 3 BR
                                                                                                      • 2 BA
                                                                                                      • 1 HF BA
                                                                                                      • Sleeps 10
                                                                                                      House #725584vb
                                                                                                      • 1 - 50 of 300+

                                                                                                      Shelter Island: Vacation Rentals (1,765)

                                                                                                       

                                                                                                      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