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Shelter Island: Houses, Cottages & More | Page 2 (1,898)

  • 51 - 100 of 1,898
Additional fees apply. Taxes may be added.
    • 4 BR
    • 2 BA
    • Sleeps 8
      • 2 BR
      • 2 BA
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        • 3 BR
        • 2 BA
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          • 4 BR
          • 3 BA
          • 1 HF BA
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          6
            • 4 BR
            • 4 BA
            • Sleeps 11
              • 4 BR
              • 3 BA
              • Sleeps 8
              1 Review
                • 3 BR
                • 1 BA
                • 1 HF BA
                • Sleeps 8
                4
                  • 4 BR
                  • 3 BA
                  • Sleeps 8
                    • 3 BR
                    • 2 BA
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                    2 Reviews
                      • 3 BR
                      • 2 BA
                      • 1 HF BA
                      • Sleeps 10
                        • 4 BR
                        • 3 BA
                        • Sleeps 10
                          View details for price
                          • 3 BR
                          • 3 BA
                          • 1 HF BA
                          • Sleeps 8
                          1 Review
                            • 5 BR
                            • 1 BA
                            • Sleeps 8
                              • 3 BR
                              • 2 BA
                              • Sleeps 7
                              5
                                • 4 BR
                                • 2 BA
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                                6
                                  • 4 BR
                                  • 3 BA
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                                  2 Reviews
                                    • 2 BR
                                    • 1 BA
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                                      • 4 BR
                                      • 2 BA
                                      • Sleeps 10
                                        • 4 BR
                                        • 4 BA
                                        • Sleeps 5
                                          • 3 BR
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                                          4
                                            • 5 BR
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                                            • 1 HF BA
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                                            2 Reviews
                                              • 3 BR
                                              • 1 BA
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                                              • Sleeps 6
                                              1 Review
                                                • 4 BR
                                                • 4 BA
                                                • Sleeps 8
                                                9
                                                  • 7 BR
                                                  • 4 BA
                                                  • Sleeps 15
                                                    • 4 BR
                                                    • 3 BA
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                                                      • 3 BR
                                                      • 3 BA
                                                      • Sleeps 8
                                                        • 2 BR
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                                                          • 4 BR
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                                                          • Sleeps 12
                                                          8
                                                            • 5 BR
                                                            • 3 BA
                                                            • Sleeps 9
                                                            4
                                                              • 5 BR
                                                              • 2 BA
                                                              • 1 HF BA
                                                              • Sleeps 8
                                                              2 Reviews
                                                                • 3 BR
                                                                • 4 BA
                                                                • Sleeps 8
                                                                1 Review
                                                                  • 4 BR
                                                                  • 2 BA
                                                                  • 1 HF BA
                                                                  • Sleeps 8
                                                                  1 Review
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • 1 HF BA
                                                                    • Sleeps 8
                                                                    1 Review
                                                                      • 4 BR
                                                                      • 2 BA
                                                                      • Sleeps 6
                                                                      2 Reviews
                                                                        • 4 BR
                                                                        • 2 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 5
                                                                          • 5 BR
                                                                          • 4 BA
                                                                          • Sleeps 8
                                                                            • 3 BR
                                                                            • 2 BA
                                                                            • 1 HF BA
                                                                            • Sleeps 6
                                                                              • 4 BR
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                                                                              4
                                                                                • 5 BR
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                                                                                • 2 HF BA
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                                                                                8
                                                                                  • 5 BR
                                                                                  • 5 BA
                                                                                  • 1 HF BA
                                                                                  • Sleeps 12
                                                                                    View details for price
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 6
                                                                                    13
                                                                                      • 2 BR
                                                                                      • 1 BA
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                                                                                      54
                                                                                        • 5 BR
                                                                                        • 4 BA
                                                                                        • Sleeps 6
                                                                                          • 4 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 8
                                                                                          2 Reviews
                                                                                            • 1 BR
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                                                                                            23
                                                                                              • 3 BR
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                                                                                              • Sleeps 8
                                                                                                • 4 BR
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                                                                                                3
                                                                                                  • 2 BR
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                                                                                                  2 Reviews
                                                                                                    • 4 BR
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                                                                                                      • 2 BR
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                                                                                                      • 51 - 100 of 1,898
                                                                                                       

                                                                                                      Recent Shelter Island Reviews

                                                                                                      Can't improve on perfection

                                                                                                      5 of 5
                                                                                                      This was truly the most charming home I have stayed in from Florida to Maine. There were four of us women, but we plan to come back with our families, because there was plenty of room, and lots of fun for the children we left at home...a charming playhouse in the large backyard, and the pool...what a treat. The sun warmed it up so there was no need for the heater. Our favorite spot was under the pergola with a bottle of wine. The kitchen was supplied with the best of cooking, baking, and serving ware. Add to this luxurious bedding, open windows, morning birdsong, and new flowers blooming in the beds each day (oh those roses!), and you'll understand why we sometimes opted to stay "home" rather than explore the delights of the area. Thanks, Pom, for sharing your bit of paradise with us.
                                                                                                      • Submitted: Jul 2, 2016
                                                                                                      • Stayed: Jun 2016

                                                                                                      Fantasy Oasis

                                                                                                      5 of 5
                                                                                                      This charming cottage is a perfect retreat for people ready to leave it all behind. The location couldn't be more perfect–it's right in the middle of the island, which means easy access to the grocery, a funky fish market, numerous farmstands, yoga at the chapel just down the street, some of the nicer restaurants on the island, and hiking in Mashomack preserve. A 5 min drive to Crescent Beach (free parking) or other quieter ones too. (It's worth getting a temporary parking pass from the town hall if you're staying for longer than the weekend). You could also totally make do with the cute bikes that come with the house. The yard is shady and big and the street is quiet, making the whole experience super chill. The owner has amazing taste—the house is decorated in a very light, airy, and thoughtful way, perfect for the island. We feel in love with this place and can't wait to come back. The owner is very sweet and accommodating. My wife and I can't wait to go back.
                                                                                                      • Submitted: Sep 18, 2015
                                                                                                      • Stayed: Aug 2015

                                                                                                      AMAZING

                                                                                                      5 of 5
                                                                                                      had an amazing 2 week stay :D
                                                                                                      • Submitted: Jul 7, 2014
                                                                                                      • Stayed: Jun 2014