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Shelter Island: Houses, Cottages & More (28)

  • 1 - 28 of 28
Additional fees apply. Taxes may be added.
    • 3 BR
    • 1 BA
    • Sleeps 5
    4
      • 3 BR
      • 2 BA
      • Sleeps 6
      3
        • 3 BR
        • 2 BA
        • Sleeps 8
          • 3 BR
          • 2 BA
          • Sleeps 8
          2 Reviews
            • 4 BR
            • 3 BA
            • Sleeps 8
              • 3 BR
              • 1 BA
              • Sleeps 8
                • 2 BR
                • 1 BA
                • Sleeps 4
                  • 2 BR
                  • 1 BA
                  • Sleeps 6
                  4
                    • 1 BR
                    • 1 BA
                    • Sleeps 2
                    10
                      • 3 BR
                      • 3 BA
                      • Sleeps 6
                        • 3 BR
                        • 2 BA
                        • Sleeps 6
                        8
                          • 3 BR
                          • 2 BA
                          • 1 HF BA
                          • Sleeps 7
                          3
                            • 2 BR
                            • 1 BA
                            • Sleeps 6
                            43
                              • 3 BR
                              • 3 BA
                              • Sleeps 10
                                • 4 BR
                                • 2 BA
                                • Sleeps 8
                                15
                                  • 3 BR
                                  • 1 BA
                                  • Sleeps 6
                                  4
                                    • 4 BR
                                    • 4 BA
                                    • Sleeps 8
                                    6
                                      • 2 BR
                                      • 1 BA
                                      • Sleeps 4
                                      14
                                        • 2 BR
                                        • 1 BA
                                        • Sleeps 6
                                        6
                                          • 3 BR
                                          • 3 BA
                                          • Sleeps 8
                                            • 3 BR
                                            • 1 BA
                                            • 1 HF BA
                                            • Sleeps 6
                                            2 Reviews
                                              • 4 BR
                                              • 3 BA
                                              • Sleeps 7
                                                • 5 BR
                                                • 3 BA
                                                • Sleeps 13
                                                  • 3 BR
                                                  • 2 BA
                                                  • 1 HF BA
                                                  • Sleeps 10
                                                  4
                                                    • 2 BR
                                                    • 1 BA
                                                    • Sleeps 4
                                                    12
                                                      • 3 BR
                                                      • 3 BA
                                                      • Sleeps 6
                                                      3
                                                        • 5 BR
                                                        • 4 BA
                                                        • Sleeps 12
                                                        2 Reviews
                                                          • 2 BR
                                                          • 1 BA
                                                          • Sleeps 6
                                                          4
                                                          • 1 - 28 of 28
                                                           

                                                          Recent Shelter Island Reviews

                                                          Perfect Getaway

                                                          5 of 5
                                                          We LOVE this house! It's perfect for our family getaway and this is the third time we've rented it. Everything is beautifully kept and the kitchen has every appliance you could dream of. Between the pool, the kayaks, and even smart TV with Netflix for the occasional rainy day, this house has it all. A 1 min walk to a beautiful bay beach and quick drive to all the others. Great location, great house, great owners! Can you tell how much we love it!? :)
                                                          • Submitted: Aug 18, 2016
                                                          • Stayed: Aug 2016

                                                          A delightful stay at The Little Grey Cottage!

                                                          5 of 5
                                                          The little grey cottage is an amazing find. Our family of four had a most delightful time and wished we had stayed longer! The home itself is adorable, well decorated with everything a vacationer could possibly need. The front closet was a treasure trove of beach accessories- blankets, chairs, toys, boogie boards- amazing. The backyard was charming; we enjoyed napping on the daybed underneath the pergola, eating meals at the outdoor dining table, and having adult beverages under the stars after the kids went to sleep. The ACs really cooled the place down making it nice for sleeping and we were thankful for Netflix when the boys (and me!) needed a little downtime. Giants Neck Beach was amazing for our little boys (6 & 3). Being on the Long Island Sound, the water was warm, the waves were small and it was shallow for a long way out. Such a special beach! We also enjoyed day trips to Mystic harbour, Mystic Aquarium and The Dinosaur Place. Great location, easy to get to and Donna & Ray thought of everything to make it an enjoyable stay!
                                                          • Submitted: Aug 16, 2016
                                                          • Stayed: Aug 2016

                                                          lovely cottage

                                                          5 of 5
                                                          My girlfriends and I stayed here in July and had a great time. The house is exactly as advertised and is very comfortable. The deck in particular was lovely in the evening! The owners were available to answer all of our questions and left great instructions for restaurants and things to do in the area. I would definitely go back!
                                                          • Submitted: Aug 5, 2016
                                                          • Stayed: Jul 2016