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Shelter Island Long Term Vacation Rentals(26)

26 Results
Book it Now!
3 - 14 night minimum stay
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
    1 Review
    Book it Now!
    2 - 3 night minimum stay
    • 6 BR,
    • 7 BA,
    • Sleeps 14
      (7)
      14 night minimum stay
      • 3 BR,
      • 3 BA,
      • Sleeps 7
        (4)
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        • 3 BR,
        • 2 BA,
        • 1 HF BA,
        • Sleeps 8
          2 Reviews
          Book it Now!
          3 night minimum stay
          • 2 BR,
          • 2 BA,
          • Sleeps 4
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            2 night minimum stay
            • 4 BR,
            • 2 BA,
            • 1 HF BA,
            • Sleeps 8
              2 Reviews
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              3 - 14 night minimum stay
              • 5 BR,
              • 2 BA,
              • 1 HF BA,
              • Sleeps 9
                1 Review
                3 - 14 night minimum stay
                • 3 BR,
                • 2 BA,
                • 1 HF BA,
                • Sleeps 6
                  (7)
                  3 - 30 night minimum stay
                  • 3 BR,
                  • 2 BA,
                  • Sleeps 6
                    (3)
                    3 - 7 night minimum stay
                    • 5 BR,
                    • 4 BA,
                    • Sleeps 10
                      (4)
                      30 night minimum stay
                      • 3 BR,
                      • 3 BA,
                      • Sleeps 8
                        3 night minimum stay
                        • 3 BR,
                        • 3 BA,
                        • Sleeps 6
                          14 night minimum stay
                          • 3 BR,
                          • 1 BA,
                          • Sleeps 3
                            7 - 30 night minimum stay
                            • 5 BR,
                            • 3 BA,
                            • 1 HF BA,
                            • Sleeps 10
                              2 - 7 night minimum stay
                              • 2 BR,
                              • 1 BA,
                              • 1 HF BA,
                              • Sleeps 6
                                • 3 BR,
                                • 3 BA,
                                • Sleeps 6
                                  10 more choices from the HomeAway Network
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                                  3 - 7 night minimum stay
                                  • 3 BR,
                                  • 3 BA,
                                  • Sleeps 10
                                    (5)
                                    Book it Now!
                                    1 - 5 night minimum stay
                                    • 4 BR,
                                    • 3 BA,
                                    • Sleeps 8
                                      1 Review
                                      Book it Now!
                                      7 - 14 night minimum stay
                                      • 2 BR,
                                      • 1 BA,
                                      • Sleeps 6
                                        2 Reviews
                                        7 night minimum stay
                                        • 4 BR,
                                        • 3 BA,
                                        • 1 HF BA,
                                        • Sleeps 10
                                          (5)
                                          $4,250 - $4,950
                                          per week
                                          7 night minimum stay
                                          • 3 BR,
                                          • 2 BA,
                                          • Sleeps 6
                                            (3)
                                            2 - 3 night minimum stay
                                            • 1 BR,
                                            • 1 BA,
                                            • Sleeps 15
                                              2 Reviews
                                              7 night minimum stay
                                              • 4 BR,
                                              • 3 BA,
                                              • Sleeps 8
                                                (4)
                                                • 7 BR,
                                                • 6 BA,
                                                • 1 HF BA,
                                                • Sleeps 16
                                                  2 Reviews
                                                  7 - 14 night minimum stay
                                                  • 1 BR,
                                                  • 1 BA,
                                                  • Sleeps 4
                                                    1 Review
                                                    7 night minimum stay
                                                    • 3 BR,
                                                    • 2 BA,
                                                    • 1 HF BA,
                                                    • Sleeps 5
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                                                      Recent Shelter Island Reviews

                                                      Beautiful Serene Retreat

                                                      5 of 5
                                                      The pictures don't capture what a lovely and surprising home this is nor how spectacular its setting. The landscaping, the views of the creek, the subtle winningness of the architecture...a great experience. We found the house warm and artfully arranged with stylish and comfortable furniture and good artwork. The overall effect is clean and organized but in an unfussy way, plus a great kitchen that would please a serious chef, all perfect for an enlightened beach house. It was such a treat to wake up to the dreamy views of the creek after a night of restful sleep on the exceptionally comfortable king-size bed. Though the weather during our stay was great - and there is plenty to do on Shelter Island/Hamptons - at times we enjoyed just lounging around the house and deck, reading, cooking, paddling around in the canoe & kayaks...we had to motivate ourselves to leave. On the one rainy day, we were happily occupied with various fun activities in the house - playing games, exercising in the basement workout room and browsing through the wonderful selection of movies on the Roku TV system. We can only imagine how cozy it would be to huddle around the fireplace in the winter months! Meanwhile, the location - minutes from ferry, beaches, shops and restaurants - could not be more convenient. The house is an easy 5-minute drive from the famed Vine Street Café and a short ferry ride away from wineries on the North Fork and the lovely, low-key town of Sag Harbor on the South Fork. The owners are super pleasant and accommodating. They left well-written notes detailing their home and Shelter Island attractions which certainly made our lives a lot easier. This is a dream of a vacation home. We look forward to our return.
                                                      • Submitted: Sep 9, 2014
                                                      • Stayed: Aug 2014

                                                      Recommend!

                                                      5 of 5
                                                      We stayed here with a group of friends and family to relax before my sister's wedding. From the outside, it looks like a historical Victorian home, but from the inside everything is completely up to date and decorated tastefully, even a bit trendy. There are plenty of areas to lounge, but we spent most of our time on the front porch facing the water and doing a little people watching. One of the best features of the house is the location. You can walk to the beach, restaurants, the North ferry, etc. I would stay here again next summer.
                                                      • Submitted: Aug 26, 2014
                                                      • Stayed: Aug 2014

                                                      Beautiful, charming home

                                                      5 of 5
                                                      We had the pleasure of spending 10 wonderful days at this fully updated, charming farmhouse. The house was extremely well maintained and the English gardens are spectacular. The beds were extremely comfortable, with crisp white bedding and the kitchen was well stocked. The children spent hours in the large, private pool. The home is extremely well located to walk to sunset (crescent) beach and Shelter Island Heights and is also close to the central part of town. There are so many great things to do in Shelter Island: beach, hiking, biking, kayaking, mini-golf, farmer's market, great restaurants and all of it was just minutes away. The owner was very responsive and helpful and made us feel at home. We would love to rent this house again.
                                                      • Submitted: Jul 9, 2014
                                                      • Stayed: Jun 2014