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Shelter Island: Houses, Condos & More (262)

  • 1 - 50 of 262
    • 2 BR
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              13
                $407
                avg/night
                • 3 BR
                • 2 BA
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                19
                  • 2 BR
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                    • 3 BR
                    • 1 BA
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                      • 2 BR
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                      6
                        $350
                        avg/night
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                        • 1 BA
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                        6
                          • 2 BR
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                            • 1 BA
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                              1 Review
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                                3
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                                  • 1 BA
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                                  11
                                    • 2 BR
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                                      • 1 BA
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                                      1 Review
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                                        18
                                          • 3 BR
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                                          4
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                                                  3
                                                    • 3 BR
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                                                    • 1 HF BA
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                                                    1 Review
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                                                      • 1 BA
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                                                      6
                                                        • 2 BR
                                                        • 1 BA
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                                                        10
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                                                          • 2 BA
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                                                          3
                                                            • 1 BR
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                                                              • 1 BR
                                                              • 1 BA
                                                              • Sleeps 4
                                                              19
                                                                • 1 BR
                                                                • 1 BA
                                                                • Sleeps 3
                                                                7
                                                                  • 2 BR
                                                                  • 1 BA
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                                                                    • 2 BA
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                                                                      • 2 BR
                                                                      • 1 BA
                                                                      • Sleeps 4
                                                                      19
                                                                        • 4 BR
                                                                        • 2 BA
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                                                                          • 2 BR
                                                                          • 1 BA
                                                                          • 1 HF BA
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                                                                            • 3 BR
                                                                            • 1 BA
                                                                            • 1 HF BA
                                                                            • Sleeps 6
                                                                              • 2 BR
                                                                              • 1 BA
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                                                                              35
                                                                                • 3 BR
                                                                                • 1 BA
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                                                                                17
                                                                                  • 2 BR
                                                                                  • 2 BA
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                                                                                  14
                                                                                    • 4 BR
                                                                                    • 2 BA
                                                                                    • 1 HF BA
                                                                                    • Sleeps 8
                                                                                      • 2 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 4
                                                                                        • 3 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 6
                                                                                          • 3 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 6
                                                                                            • 4 BR
                                                                                            • 2 BA
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                                                                                            10
                                                                                              • 3 BR
                                                                                              • 2 BA
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                                                                                              13
                                                                                                • 2 BR
                                                                                                • 1 BA
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                                                                                                  • 5 BR
                                                                                                  • Sleeps 8
                                                                                                    • 2 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 5
                                                                                                      • 2 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 5
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                                                                                                      Recent Shelter Island Reviews

                                                                                                      Incredible Beach Front Cottage

                                                                                                      5 of 5
                                                                                                      The Clam Rake Cottage is a jewel of a place to stay if you want to experience the ultimate beach getaway. It's an adorable cottage perfectly furnished with the essentials for everything you will need at the beach. Complete with Kayacks, a sunfish sailboat, hammock and tons of lounge chairs and beach umbrellas. There is even a hot tub! Susan couldn't have been nicer with all the correspondence and answering questions about her home and the village of Orient. She was extremely accommodating and quick with any emails. The village of Orient is a serene dreamy town that is like no place on earth- you essentially are stepped back to a time when life slows down. Highlights of living life in Orient include - walks on the beach - kayacking - sailing - and enjoying this jewel like village that has the most adorable general store where you can enjoy gourmet sandwiches - specially desserts and a friendliness you won't find elsewhere - also Brooklyn's 4 and 20 Pies has an outpost here where you can enjoy delicious pies and very good stumptown coffee. There are no restaurants in town which add to the simplicity of the slowness and being not in a touristy place. If I could give the Clam Rake Cottage 10 stars - it would be hands down !!! If you are looking for the perfect beach getaway - then look no further at this adorable Cottage for your next holiday- I can't wait to return !
                                                                                                      • Submitted: Aug 20, 2016
                                                                                                      • Stayed: Aug 2016

                                                                                                      Sunny and stylish - great location

                                                                                                      5 of 5
                                                                                                      We had a lovely 4 day weekend at this stylish little cottage within walking distance of the village of Sag Harbor, tennis courts, a playground etc. The back yard was spacious enough for the kids to play and provided ample sun and shade. The kitchen was small but well stocked with anything you need to cook. We know the area very well and this was the perfect spot to take advantage of all!
                                                                                                      • Submitted: Aug 5, 2016
                                                                                                      • Stayed: Jul 2016

                                                                                                      All good. All as advertised.

                                                                                                      5 of 5
                                                                                                      No problem. Central air key during our warm summer stay. Excellent bikes & kayaks a really nice bonus. We're goin back. 👍🏻
                                                                                                      • Submitted: Jul 31, 2016
                                                                                                      • Stayed: Jul 2016