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Shelter Island Waterfront Vacation Rentals Vacation Rentals(31)

31 Results
7 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 10
    (9)
    Book it Now!
    3 - 14 night minimum stay
    • 4 BR,
    • 4 BA,
    • 1 HF BA,
    • Sleeps 10
      1 Review
      Book it Now!
      14 - 30 night minimum stay
      • 3 BR,
      • 2 BA,
      • Sleeps 8
        • 4 BR,
        • 3 BA,
        • Sleeps 7
          (4)
          Book it Now!
          3 night minimum stay
          • 2 BR,
          • 2 BA,
          • Sleeps 4
            $500 - $600
            per night
            Book it Now!
            3 night minimum stay
            • 2 BR,
            • 2 BA,
            • Sleeps 4
              7 night minimum stay
              • 2 BR,
              • 1 BA,
              • Sleeps 4
                (4)
                3 - 7 night minimum stay
                • 5 BR,
                • 4 BA,
                • Sleeps 10
                  (4)
                  7 night minimum stay
                  • 2 BR,
                  • 1 BA,
                  • Sleeps 6
                    (6)
                    30 - 31 night minimum stay
                    • 5 BR,
                    • 4 BA,
                    • 1 HF BA,
                    • Sleeps 6
                      1 Review
                      3 - 31 night minimum stay
                      • 4 BR,
                      • 3 BA,
                      • Sleeps 9
                        1 Review
                        30 night minimum stay
                        • 3 BR,
                        • 3 BA,
                        • Sleeps 8
                          2 - 7 night minimum stay
                          • 2 BR,
                          • 1 BA,
                          • 1 HF BA,
                          • Sleeps 6
                            • 3 BR,
                            • 3 BA,
                            • Sleeps 6
                              3 night minimum stay
                              • 2 BR,
                              • 2 BA,
                              • 1 HF BA,
                              • Sleeps 4
                                (11)
                                3 - 7 night minimum stay
                                • 3 BR,
                                • Sleeps 8
                                  2 Reviews
                                  $500
                                  per night
                                  3 - 31 night minimum stay
                                  • 5 BR,
                                  • 2 BA,
                                  • Sleeps 9
                                    1 Review
                                    6 night minimum stay
                                    • 4 BR,
                                    • 3 BA,
                                    • Sleeps 10
                                      1 Review
                                      7 night minimum stay
                                      • 5 BR,
                                      • 2 BA,
                                      • Sleeps 9
                                        (3)
                                        3 night minimum stay
                                        • 3 BR,
                                        • 2 BA,
                                        • Sleeps 7
                                          1 Review
                                          • 7 BR,
                                          • 6 BA,
                                          • 1 HF BA,
                                          • Sleeps 16
                                            2 Reviews
                                            7 - 14 night minimum stay
                                            • 1 BR,
                                            • 1 BA,
                                            • Sleeps 4
                                              1 Review
                                              • Studio,
                                              • 1 BA,
                                              • Sleeps 14
                                                7 night minimum stay
                                                • 3 BR,
                                                • 2 BA,
                                                • 1 HF BA,
                                                • Sleeps 5
                                                  • 4 BR,
                                                  • 3 BA,
                                                  • 1 HF BA,
                                                  • Sleeps 8
                                                    (6)
                                                    • 4 BR,
                                                    • 3 BA,
                                                    • Sleeps 12
                                                      (4)
                                                      30 night minimum stay
                                                      • 4 BR,
                                                      • 4 BA,
                                                      • Sleeps 10
                                                        (3)
                                                        2 - 7 night minimum stay
                                                        • 3 BR,
                                                        • 2 BA,
                                                        • 1 HF BA,
                                                        • Sleeps 8
                                                          7 night minimum stay
                                                          • 3 BR,
                                                          • 4 BA,
                                                          • Sleeps 4
                                                            • 2 BR,
                                                            • 2 BA,
                                                            • Sleeps 6
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                                                              Recent Shelter Island Reviews

                                                              Beautiful Serene Retreat

                                                              5 of 5
                                                              The pictures don't capture what a lovely and surprising home this is nor how spectacular its setting. The landscaping, the views of the creek, the subtle winningness of the architecture...a great experience. We found the house warm and artfully arranged with stylish and comfortable furniture and good artwork. The overall effect is clean and organized but in an unfussy way, plus a great kitchen that would please a serious chef, all perfect for an enlightened beach house. It was such a treat to wake up to the dreamy views of the creek after a night of restful sleep on the exceptionally comfortable king-size bed. Though the weather during our stay was great - and there is plenty to do on Shelter Island/Hamptons - at times we enjoyed just lounging around the house and deck, reading, cooking, paddling around in the canoe & kayaks...we had to motivate ourselves to leave. On the one rainy day, we were happily occupied with various fun activities in the house - playing games, exercising in the basement workout room and browsing through the wonderful selection of movies on the Roku TV system. We can only imagine how cozy it would be to huddle around the fireplace in the winter months! Meanwhile, the location - minutes from ferry, beaches, shops and restaurants - could not be more convenient. The house is an easy 5-minute drive from the famed Vine Street Café and a short ferry ride away from wineries on the North Fork and the lovely, low-key town of Sag Harbor on the South Fork. The owners are super pleasant and accommodating. They left well-written notes detailing their home and Shelter Island attractions which certainly made our lives a lot easier. This is a dream of a vacation home. We look forward to our return.
                                                              • Submitted: Sep 9, 2014
                                                              • Stayed: Aug 2014

                                                              Charming Cottage and Terrific Owners

                                                              5 of 5
                                                              We had a wonderful multi-week stay here. The house is as charming as advertised. We swam off the dock every day. Also kept my 20' sailboat at the dock and had great fun sailing in Gardner's bay. Topping it all off, the owners were a delight to deal with as we settled in and got our bearings. If you're considering this property give it a go, you'll be glad you did!
                                                              • Submitted: Aug 24, 2014
                                                              • Stayed: Jun 2014

                                                              Gorgeous refuge

                                                              5 of 5
                                                              This place is a gem. The rooms are cozy and clean, but the best places to savor the property are the screened porch, the hammock, the Adirondack chairs facing the water, and dining in the converted garage with a view of the creek. We loved having access to the kayak and the grill, our kids loved the swing, and we rented bikes practically next door. Birders will love seeing ospreys that nest all over the island, the egrets gracing the creek, and all variety of smaller birds congregating at the feeders. The owner was gracious and exceedingly helpful; during our stay he responded promptly to our Qs about the property and places to visit on the island. I would definitely look into staying here again on our next visit to Shelter Island.
                                                              • Submitted: Aug 19, 2014
                                                              • Stayed: Jul 2014