check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar
Cancel Clear Filters Apply Filters

Property Type

Booking Options

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Shelter Island: Houses, Cottages & More

  • 1 - 50
Additional fees apply. Taxes may be added.
    Exceptional! 5.0/5
    (14 reviews)
    avg/night
    • 5 BR
    • 3 BA
    • Sleeps 10
    14
      • 4 BR
      • 4 BA
      • 1 HF BA
      • Sleeps 10
      3
        • 4 BR
        • 2 BA
        • Sleeps 10
        8
          • 5 BR
          • 4 BA
          • 1 HF BA
          • Sleeps 6
          2 Reviews
            • 4 BR
            • 3 BA
            • 1 HF BA
            • Sleeps 10
              • 6 BR
              • 4 BA
              • 2 HF BA
              • Sleeps 12
                • 4 BR
                • 4 BA
                • 1 HF BA
                • Sleeps 7
                2 Reviews
                  • 4 BR
                  • 3 BA
                  • Sleeps 7
                  10
                    • 5 BR
                    • 3 BA
                    • Sleeps 12
                    1 Review
                      Exceptional! 5.0/5
                      (25 reviews)
                      avg/night
                      • 2 BR
                      • 1 BA
                      • Sleeps 4
                      25
                        • 3 BR
                        • 3 BA
                        • Sleeps 7
                        2 Reviews
                          • 2 BR
                          • 2 BA
                          • Sleeps 6
                          3
                            • 4 BR
                            • 2 BA
                            • Sleeps 8
                            8
                              NEW!
                              • 3 BR
                              • 2 BA
                              • Sleeps 6
                                • 3 BR
                                • 2 BA
                                • Sleeps 6
                                  • 3 BR
                                  • 2 BA
                                  • Sleeps 5
                                  14
                                    • 4 BR
                                    • 2 BA
                                    • Sleeps 8
                                    2 Reviews
                                      • 4 BR
                                      • 3 BA
                                      • 2 HF BA
                                      • Sleeps 8
                                      8
                                        Exceptional! 5.0/5
                                        (11 reviews)
                                        avg/night
                                        • 4 BR
                                        • 2 BA
                                        • 1 HF BA
                                        • Sleeps 9
                                        11
                                          • 2 BR
                                          • 1 BA
                                          • Sleeps 6
                                          9
                                            Wonderful! 4.8/5
                                            (5 reviews)
                                            View details for price
                                            • 3 BR
                                            • 2 BA
                                            • 1 HF BA
                                            • Sleeps 8
                                            5
                                              • 3 BR
                                              • 1 BA
                                              • Sleeps 8
                                              5
                                                Exceptional! 5.0/5
                                                (17 reviews)
                                                avg/night
                                                • 3 BR
                                                • 2 BA
                                                • Sleeps 8
                                                17
                                                  • 4 BR
                                                  • 1 BA
                                                  • Sleeps 8
                                                  4
                                                    • 3 BR
                                                    • 1 BA
                                                    • Sleeps 6
                                                    7
                                                      • 3 BR
                                                      • 2 BA
                                                      • Sleeps 6
                                                      7
                                                        • 4 BR
                                                        • 3 BA
                                                        • Sleeps 8
                                                        4
                                                          • 3 BR
                                                          • Sleeps 8
                                                          2 Reviews
                                                            • 3 BR
                                                            • 2 BA
                                                            • Sleeps 6
                                                            1 Review
                                                              Excellent! 4.7/5
                                                              (9 reviews)
                                                              avg/night
                                                              • 4 BR
                                                              • 3 BA
                                                              • Sleeps 10
                                                              9
                                                                • 4 BR
                                                                • 2 BA
                                                                • Sleeps 5
                                                                  • 3 BR
                                                                  • 2 BA
                                                                  • Sleeps 6
                                                                  1 Review
                                                                    Wonderful! 4.9/5
                                                                    (8 reviews)
                                                                    avg/night
                                                                    • 3 BR
                                                                    • 3 BA
                                                                    • Sleeps 10
                                                                    8
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Sleeps 6
                                                                      2 Reviews
                                                                        • 5 BR
                                                                        • 2 BA
                                                                        • Sleeps 12
                                                                        5
                                                                          • 4 BR
                                                                          • 2 BA
                                                                          • Sleeps 8
                                                                            Exceptional! 5.0/5
                                                                            (5 reviews)
                                                                            avg/night
                                                                            • 2 BR
                                                                            • 1 BA
                                                                            • Sleeps 4
                                                                            5
                                                                              • 5 BR
                                                                              • 4 BA
                                                                              • Sleeps 12
                                                                              4
                                                                                • 2 BR
                                                                                • 2 BA
                                                                                • Sleeps 4
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • 1 HF BA
                                                                                  • Sleeps 6
                                                                                  2 Reviews
                                                                                    • 4 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 8
                                                                                      Exceptional! 5.0/5
                                                                                      (9 reviews)
                                                                                      avg/night
                                                                                      • 4 BR
                                                                                      • 3 BA
                                                                                      • Sleeps 12
                                                                                      9
                                                                                        • 4 BR
                                                                                        • 4 BA
                                                                                        • Sleeps 5
                                                                                          • 3 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 6
                                                                                          4
                                                                                            Excellent! 4.5/5
                                                                                            (6 reviews)
                                                                                            avg/night
                                                                                            • 4 BR
                                                                                            • 3 BA
                                                                                            • 1 HF BA
                                                                                            • Sleeps 8
                                                                                            6
                                                                                              • 4 BR
                                                                                              • 2 BA
                                                                                              • 1 HF BA
                                                                                              • Sleeps 7
                                                                                                View details for price
                                                                                                • 4 BR
                                                                                                • 3 BA
                                                                                                • Sleeps 8
                                                                                                  • 3 BR
                                                                                                  • 1 BA
                                                                                                  • 1 HF BA
                                                                                                  • Sleeps 8
                                                                                                  4
                                                                                                    Excellent! 4.6/5
                                                                                                    (5 reviews)
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 7
                                                                                                    5
                                                                                                      • 4 BR
                                                                                                      • 3 BA
                                                                                                      • Sleeps 6
                                                                                                      2 Reviews
                                                                                                      • 1 - 50
                                                                                                       

                                                                                                      Recent Shelter Island Reviews

                                                                                                      The house is lovely, we found it very clean and comfortable.

                                                                                                      5 of 5
                                                                                                      This is a great place for an easy vacation. The house was very well stocked and immaculately clean. The best part was the close proximity to the beach.
                                                                                                      • Submitted: Sep 17, 2016
                                                                                                      • Stayed: Sep 2016

                                                                                                      Great location - very open

                                                                                                      5 of 5
                                                                                                      Great location- open - decks for outdoor eating and relaxing
                                                                                                      • Submitted: Aug 29, 2016
                                                                                                      • Stayed: Aug 2016

                                                                                                      Wonderful vacation

                                                                                                      5 of 5
                                                                                                      Eden Roc is a magical house. We all loved sitting on the beautiful porch looking at the water and the osprey. The decor is perfect and it's location in the heart of the village allowed us to walk to restaurants and shops. One of the best vacation houses ever!
                                                                                                      • Submitted: Aug 11, 2016
                                                                                                      • Stayed: Aug 2016