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    • 3 BR
    • 2 BA
    • Sleeps 6
    House #321313
    4
      • 4 BR
      • 2 BA
      • Sleeps 10
      House #446286
      8
        • 3 BR
        • 1 BA
        • Sleeps 6
        House #694738
        13
          • 3 BR
          • 2 BA
          • Sleeps 6
          Bungalow #804815
          22
            • 3 BR
            • 2 BA
            • Sleeps 6
            House #3554393ha
            17
              Excellent! 4.6/5
              (7 reviews)
              avg/night
              • 3 BR
              • 2 BA
              • 1 HF BA
              • Sleeps 6
              House #3621885ha
              7
                • 3 BR
                • 2 BA
                • Sleeps 6
                House #803084
                2
                  • 4 BR
                  • 3 BA
                  • 2 HF BA
                  • Sleeps 8
                  House #746110
                  13
                    • 3 BR
                    • 2 BA
                    • Sleeps 6
                    House #891646
                    1
                      • 4 BR
                      • 3 BA
                      • Sleeps 10
                      House #476247
                      11
                        Exceptional! 5/5
                        (6 reviews)
                        avg/night
                        • 3 BR
                        • 2 BA
                        • Sleeps 8
                        House #3925407ha
                        6
                          • 3 BR
                          • 2 BA
                          • 1 HF BA
                          • Sleeps 6
                          House #894525
                            • 4 BR
                            • 2 BA
                            • Sleeps 10
                            Farmhouse #3767828ha
                            12
                              Exceptional! 5/5
                              (7 reviews)
                              View details for price
                              • 3 BR
                              • 3 BA
                              • Sleeps 6
                              House #3594708ha
                              7
                                • 3 BR
                                • 2 BA
                                • Sleeps 7
                                House #908170
                                2
                                  • 5 BR
                                  • 3 BA
                                  • Sleeps 10
                                  House #3781403ha
                                  2
                                    • 3 BR
                                    • 2 BA
                                    • Sleeps 6
                                    Cottage #702619
                                    7
                                      Exceptional! 5/5
                                      (13 reviews)
                                      avg/night
                                      • 3 BR
                                      • 3 BA
                                      • 1 HF BA
                                      • Sleeps 6
                                      House #304851
                                      13
                                        Exceptional! 5/5
                                        (6 reviews)
                                        avg/night
                                        • 4 BR
                                        • 3 BA
                                        • Sleeps 8
                                        House #411447
                                        6
                                          • 4 BR
                                          • 3 BA
                                          • Sleeps 10
                                          House #425548
                                          14
                                            • 5 BR
                                            • 4 BA
                                            • Sleeps 12
                                            House #344072
                                            6
                                              • 2 BR
                                              • 1 BA
                                              • Sleeps 6
                                              Cottage #360888
                                              18
                                                • 3 BR
                                                • 2 BA
                                                • Sleeps 6
                                                House #4522864ha
                                                  • 4 BR
                                                  • 2 BA
                                                  • Sleeps 8
                                                  Cottage #556885
                                                  1
                                                    • 4 BR
                                                    • 3 BA
                                                    • 1 HF BA
                                                    • Sleeps 10
                                                    House #1050826
                                                    1
                                                      • 5 BR
                                                      • 2 BA
                                                      • Sleeps 12
                                                      House #628856
                                                      5
                                                        Wonderful! 4.9/5
                                                        (8 reviews)
                                                        avg/night
                                                        • 3 BR
                                                        • 3 BA
                                                        • Sleeps 10
                                                        House #305998
                                                        8
                                                          • 2 BR
                                                          • 2 BA
                                                          • Sleeps 4
                                                          House #3596889ha
                                                            • 3 BR
                                                            • 2 BA
                                                            • Sleeps 5
                                                            House #1073110
                                                              • 5 BR
                                                              • 3 BA
                                                              • Sleeps 9
                                                              House #412629
                                                              4
                                                                • 5 BR
                                                                • 3 BA
                                                                • 1 HF BA
                                                                • Sleeps 9
                                                                Farmhouse #683544
                                                                2
                                                                  • 5 BR
                                                                  • 4 BA
                                                                  • Sleeps 10
                                                                  House #1015933
                                                                    • 4 BR
                                                                    • 4 BA
                                                                    • 1 HF BA
                                                                    • Sleeps 7
                                                                    House #3757374ha
                                                                    4
                                                                      • 1 BR
                                                                      • 1 BA
                                                                      • Sleeps 4
                                                                      Cottage #4479416ha
                                                                      1
                                                                        • 3 BR
                                                                        • 3 BA
                                                                        • Sleeps 6
                                                                        House #885475
                                                                          • 3 BR
                                                                          • 1 BA
                                                                          • Sleeps 6
                                                                          Cottage #4499810ha
                                                                            • 4 BR
                                                                            • 3 BA
                                                                            • Sleeps 7
                                                                            House #352116
                                                                            10
                                                                              • 5 BR
                                                                              • 3 BA
                                                                              • Sleeps 12
                                                                              House #480215
                                                                              6
                                                                                • 2 BR
                                                                                • 1 BA
                                                                                • Sleeps 6
                                                                                House #4269044ha
                                                                                1
                                                                                  • 3 BR
                                                                                  • 1 HF BA
                                                                                  • Sleeps 6
                                                                                  House #4570385ha
                                                                                    • 5 BR
                                                                                    • 4 BA
                                                                                    • Sleeps 8
                                                                                    House #4515640ha
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 6
                                                                                      House #250830ha
                                                                                      4
                                                                                        • 5 BR
                                                                                        • 3 BA
                                                                                        • 1 HF BA
                                                                                        • Sleeps 10
                                                                                        House #716643
                                                                                        10
                                                                                          • 4 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 8
                                                                                          House #857206
                                                                                          1
                                                                                            • 3 BR
                                                                                            • 3 BA
                                                                                            • Sleeps 7
                                                                                            House #326053ha
                                                                                            3
                                                                                              • 3 BR
                                                                                              • 4 BA
                                                                                              • Sleeps 8
                                                                                              House #631622
                                                                                              3
                                                                                                • 4 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 8
                                                                                                House #3931482ha
                                                                                                2
                                                                                                  • 4 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 8
                                                                                                  Cottage #4062137ha
                                                                                                  2
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 6
                                                                                                    House #965493
                                                                                                      • 3 BR
                                                                                                      • 1 BA
                                                                                                      • 1 HF BA
                                                                                                      • Sleeps 6
                                                                                                      House #292262
                                                                                                      4
                                                                                                      • 1 - 50 of 300+
                                                                                                       

                                                                                                      Recent Shelter Island Reviews

                                                                                                      A beautiful home, naturalistic inspired.

                                                                                                      5 of 5
                                                                                                      We had great family time re-connecting and enjoying the best nature has to give. Love the beaches, combing and collecting.
                                                                                                      • Submitted: Jul 16, 2017
                                                                                                      • Stayed: Jul 2017

                                                                                                      Just a wonderful, wonderful spot

                                                                                                      5 of 5
                                                                                                      We stayed at the cottage on Westmoreland Farm for six days in June. The cottage itself is modest but completely charming and well-maintained. It reminds me of a time when vacations in New England were more about modesty and getting away, not about ostentation. I can't say enough about the friendliness and welcoming spirit of the owners, Margaret and Karl, who made sure that we found our way, greeted us upon arrival, and helped with anything we needed during our stay. They even stocked the refrigerator with some eggs from their chickens. Note that when you do stay at this cottage you are participating in a little bit of history. Westmoreland Farm was a sprawling Victorian project, which has now been in the same family since the 1930s. It is a blessed piece of land with lots of family history. A perfect setting for enjoying the calm and quiet of Shelter Island. After a day out, there's nothing better to returning to the cottage and enjoying the sun setting over the lake.
                                                                                                      • Submitted: Jun 29, 2017
                                                                                                      • Stayed: Jun 2017