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Shelter Island Vacation Rentals(92)

92 Results
7 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 10
    (9)
    • 6 BR,
    • 4 BA,
    • 2 HF BA,
    • Sleeps 12
      Book it Now!
      • 6 BR,
      • 4 BA,
      • Sleeps 14
        2 Reviews
        • 7 BR,
        • 8 BA,
        • Sleeps 20
          Book it Now!
          3 - 14 night minimum stay
          • 4 BR,
          • 4 BA,
          • 1 HF BA,
          • Sleeps 10
            1 Review
            7 - 31 night minimum stay
            • 5 BR,
            • 3 BA,
            • Sleeps 12
              1 Review
              Book it Now!
              • 3 BR,
              • 3 BA,
              • Sleeps 7
                Book it Now!
                2 - 3 night minimum stay
                • 6 BR,
                • 7 BA,
                • Sleeps 14
                  (7)
                  30 night minimum stay
                  • 2 BR,
                  • 2 BA,
                  • Sleeps 6
                    (3)
                    4 night minimum stay
                    • 4 BR,
                    • 3 BA,
                    • 2 HF BA,
                    • Sleeps 12
                      (5)
                      • 4 BR,
                      • 3 BA,
                      • Sleeps 7
                        (4)
                        14 night minimum stay
                        • 3 BR,
                        • 3 BA,
                        • Sleeps 7
                          (4)
                          7 night minimum stay
                          • 3 BR,
                          • 2 BA,
                          • Sleeps 6
                            (3)
                            $2,275 - $2,450
                            per week
                            Book it Now!
                            7 night minimum stay
                            • 3 BR,
                            • 2 BA,
                            • Sleeps 6
                              (3)
                              Book it Now!
                              • 3 BR,
                              • 2 BA,
                              • 1 HF BA,
                              • Sleeps 8
                                2 Reviews
                                Book it Now!
                                3 night minimum stay
                                • 2 BR,
                                • 2 BA,
                                • Sleeps 4
                                  Book it Now!
                                  2 night minimum stay
                                  • 4 BR,
                                  • 2 BA,
                                  • 1 HF BA,
                                  • Sleeps 8
                                    2 Reviews
                                    Book it Now!
                                    3 - 14 night minimum stay
                                    • 5 BR,
                                    • 2 BA,
                                    • 1 HF BA,
                                    • Sleeps 9
                                      1 Review
                                      Book it Now!
                                      6 - 28 night minimum stay
                                      • 3 BR,
                                      • 2 BA,
                                      • Sleeps 8
                                        1 Review
                                        3 - 30 night minimum stay
                                        • 3 BR,
                                        • 2 BA,
                                        • Sleeps 6
                                          (3)
                                          Book it Now!
                                          • 2 BR,
                                          • 2 BA,
                                          • Sleeps 6
                                            $3,500 - $3,850
                                            per week
                                            Book it Now!
                                            14 - 30 night minimum stay
                                            • 4 BR,
                                            • 3 BA,
                                            • Sleeps 8
                                              7 - 30 night minimum stay
                                              • 3 BR,
                                              • 2 BA,
                                              • Sleeps 6
                                                (3)
                                                3 - 31 night minimum stay
                                                • 4 BR,
                                                • 3 BA,
                                                • Sleeps 9
                                                  1 Review
                                                  7 night minimum stay
                                                  • 2 BR,
                                                  • 1 BA,
                                                  • Sleeps 4
                                                    (4)
                                                    27 - 30 night minimum stay
                                                    • 4 BR,
                                                    • 3 BA,
                                                    • Sleeps 8
                                                      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
                                                            30 night minimum stay
                                                            • 3 BR,
                                                            • 3 BA,
                                                            • Sleeps 8
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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

                                                              Beautiful home, perfect vacation

                                                              5 of 5
                                                              My wife and I were lucky enough to find this home and spend our July out there. Could not have been a more perfect stay. Home is meticulously designed and decorated, an open sunny home during the day and a warm retreat at night. The garden and pool is a perfect oasis and a great place to forget about day to day life and relax. Shelter Island itself is serene and has everything you could want from a summer vacation. Beaches and boating and barbecues or a short trip to the hamptons and the ocean. Hoping to make it back again next summer!
                                                              • Submitted: Sep 9, 2014
                                                              • Stayed: Jul 2014

                                                              Heavenly!

                                                              5 of 5
                                                              This place is a true treasure. Incredibly comfortable home with everything we could need on hand. Ceiling fans in every room make the place so cool and breezy that we barely needed the a/c despite the heat. I've never rented a house before and went with very low expectations- brought my own towels, sheets, utensils, plates, and needed none of it as everything was clean and comfortable and lovely. The screened-in porch was a delight. My kids had a blast watching the deer in the early morning and early evening, and the tire swing was a HUGE bonus and total surprise! My daughter lost her mind with joy to discover that. and us grownups relished the hammock and the plentiful and very comfy chairs and sofas. The pool was perfect- my crew has little tolerance for cold water so the heater was fantastic and the hot tub another treat. The views of the massive and gorgeous property were spectacular and there were wonderful views from every room. I can't stop raving about this house and the property and the location was fantastic as well. Nothing was more than 5 minutes away. We fell in love with Whale's Tale for mini golf and I am still dreaming about Commander Cody's fried scallops. I grew up going to the Hamptons and had never been to Shelter Island and was thrilled to experience this treasure- beautiful and even on Labor Day weekend not a crowd or single incident of traffic to be found. Celina was extremely helpful, very responsive to questions and returned my security deposit within one day! Only thing to note is that the laundry and second bathroom are in the basement, and that was a bit tricky to find- it's the door in the screened in porch! I can't recommend this property enough and am already plotting my next stay here. Thank you so much, Celina and Tom for making our stay just glorious!
                                                              • Submitted: Sep 3, 2014
                                                              • Stayed: Aug 2014