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Shelter Island: Houses, Cottages & More (171)

  • 1 - 30 of 171
    • 1 BR
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      10
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        • 4 BR
        • 4 BA
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          • 6 BR
          • 6 BA
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          • Sleeps 10
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            • 2 BR
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            12
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              • 2 BR
              • 1 BA
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              46
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                • 5 BR
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                6
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                  • 4 BR
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                  11
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                    • 4 BR
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                    7
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                      • 6 BR
                      • 4 BA
                      • 2 HF BA
                      • Sleeps 10
                      8
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                        • 3 BR
                        • 3 BA
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                        • Sleeps 10
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                          • 5 BR
                          • 4 BA
                          • 1 HF BA
                          • Sleeps 6
                          1 Review
                            • 4 BR
                            • 3 BA
                            • 1 HF BA
                            • Sleeps 10
                              • 3 BR
                              • 3 BA
                              • Sleeps 6
                                • 6 BR
                                • 4 BA
                                • 2 HF BA
                                • Sleeps 12
                                  • 4 BR
                                  • 4 BA
                                  • 1 HF BA
                                  • Sleeps 7
                                  2 Reviews
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                                    • 5 BR
                                    • 3 BA
                                    • 1 HF BA
                                    • Sleeps 10
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                                      • 7 BR
                                      • 7 BA
                                      • 1 HF BA
                                      • Sleeps 14
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                                      Special Offer! SPECIAL PRICING FOR ENTIRE SUMMER ! MEMORIAL TO LABOR DAY May 30 - September 5
                                        • 4 BR
                                        • 3 BA
                                        • Sleeps 7
                                        7
                                          • 5 BR
                                          • 3 BA
                                          • Sleeps 12
                                          1 Review
                                            • 3 BR
                                            • 2 BA
                                            • Sleeps 8
                                            2 Reviews
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                                              • 3 BR
                                              • 3 BA
                                              • Sleeps 7
                                              2 Reviews
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                                                • 3 BR
                                                • 2 BA
                                                • Sleeps 10
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                                                  • 6 BR
                                                  • 7 BA
                                                  • Sleeps 14
                                                  10
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                                                    • 2 BR
                                                    • 2 BA
                                                    • Sleeps 6
                                                    3
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                                                      • 4 BR
                                                      • 2 BA
                                                      • 2 HF BA
                                                      • Sleeps 10
                                                      6
                                                        • 1 BR
                                                        • 1 BA
                                                        • Sleeps 2
                                                        16
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                                                          • 4 BR
                                                          • 2 BA
                                                          • Sleeps 8
                                                          6
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                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 2
                                                            12
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                                                              • 1 BR
                                                              • 1 BA
                                                              • Sleeps 4
                                                              20
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                                                              • 1 - 30 of 171
                                                               

                                                              Recent Shelter Island Reviews

                                                              Quiet & Serene Escape

                                                              5 of 5
                                                              My family and I had an amazing time staying at the house last Fall (one of our favorite seasons to visit the North Fork). The house is in the perfect location for taking advantage of all that the area has to offer, but at the same time has a secluded feel that makes you feel like you're actually getting away from it all. Less than a 10 minute drive and your in Greenport where there is more "action" (restaurants, shops, bars, etc.) or there are fantastic wineries to explore in an even shorter drive from the house. The house and location has an in-the-woods feel, but with a views of the Shelter Island in the mere distance. Everything was clean and well organized with all the amenities we could ever need for a care free vacation. The beautiful pool area was icing on the cake. We can't wait to come back!
                                                              • Submitted: Apr 14, 2016
                                                              • Stayed: Oct 2015

                                                              Great stay in Greenport!

                                                              5 of 5
                                                              The house could not have been more perfect for our vacation, it was absolutely gorgeous and very spacious. We were a few blocks from town and close to the LIRR and Jitney stops which was great for those of us traveling from the city. The host was very responsive and accommodating. They didn't miss a beat, the kitchen was fully stocked with pots, pans, plates, etc. and there were plenty of fresh towels for the long weekend. We will definitely be back for our next trip out east. Thanks so much!
                                                              • Submitted: Apr 8, 2016
                                                              • Stayed: Apr 2016

                                                              Beautiful home

                                                              5 of 5
                                                              My husband and I rented this property with friends last fall and had a great time. The house was comfortable, spotless and generously appointed with anything you could possible need. A lovely secluded location close to the village. Highly recommended.
                                                              • Submitted: Mar 10, 2016
                                                              • Stayed: Sep 2015