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Shelter Island Vacation Rentals(63)

63 Results
7 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 10
    (9)
    7 night minimum stay
    • 3 BR,
    • 2 BA,
    • Sleeps 6
      (3)
      7 night minimum stay
      • 3 BR,
      • 2 BA,
      • 1 HF BA,
      • Sleeps 4
        2 Reviews
        • 4 BR,
        • 2 BA,
        • Sleeps 9
          1 Review
          7 - 31 night minimum stay
          • 5 BR,
          • 3 BA,
          • Sleeps 12
            1 Review
            Book it Now!
            2 - 3 night minimum stay
            • 6 BR,
            • 7 BA,
            • Sleeps 14
              (7)
              30 night minimum stay
              • 2 BR,
              • 2 BA,
              • Sleeps 6
                2 Reviews
                2 - 9 night minimum stay
                • 4 BR,
                • 3 BA,
                • 2 HF BA,
                • Sleeps 12
                  (5)
                  14 night minimum stay
                  • 3 BR,
                  • 3 BA,
                  • Sleeps 7
                    (4)
                    4 - 14 night minimum stay
                    • 4 BR,
                    • 3 BA,
                    • Sleeps 7
                      (3)
                      $2,275 - $3,500
                      per week
                      Book it Now!
                      7 night minimum stay
                      • 3 BR,
                      • 2 BA,
                      • Sleeps 6
                        (3)
                        Book it Now!
                        3 night minimum stay
                        • 3 BR,
                        • 2 BA,
                        • 1 HF BA,
                        • Sleeps 8
                          1 Review
                          Book it Now!
                          7 night minimum stay
                          • 6 BR,
                          • 4 BA,
                          • Sleeps 14
                            2 Reviews
                            Book it Now!
                            2 night minimum stay
                            • 4 BR,
                            • 2 BA,
                            • 1 HF BA,
                            • Sleeps 8
                              2 Reviews
                              Book it Now!
                              3 - 14 night minimum stay
                              • 5 BR,
                              • 2 BA,
                              • 1 HF BA,
                              • Sleeps 9
                                1 Review
                                Book it Now!
                                6 - 28 night minimum stay
                                • 3 BR,
                                • 2 BA,
                                • Sleeps 8
                                  1 Review
                                  3 - 30 night minimum stay
                                  • 3 BR,
                                  • 2 BA,
                                  • Sleeps 6
                                    (3)
                                    3 - 14 night minimum stay
                                    • 3 BR,
                                    • 2 BA,
                                    • 1 HF BA,
                                    • Sleeps 6
                                      (7)
                                      7 - 30 night minimum stay
                                      • 3 BR,
                                      • 2 BA,
                                      • Sleeps 6
                                        2 Reviews
                                        7 night minimum stay
                                        • 2 BR,
                                        • 1 BA,
                                        • Sleeps 4
                                          (4)
                                          27 - 30 night minimum stay
                                          • 4 BR,
                                          • 3 BA,
                                          • Sleeps 8
                                            7 night minimum stay
                                            • 2 BR,
                                            • 1 BA,
                                            • Sleeps 6
                                              (6)
                                              30 - 31 night minimum stay
                                              • 5 BR,
                                              • 4 BA,
                                              • 1 HF BA,
                                              • Sleeps 6
                                                1 Review
                                                14 night minimum stay
                                                • 3 BR,
                                                • 3 BA,
                                                • Sleeps 8
                                                  3 - 31 night minimum stay
                                                  • 4 BR,
                                                  • 3 BA,
                                                  • Sleeps 9
                                                    1 Review
                                                    3 - 7 night minimum stay
                                                    • 5 BR,
                                                    • 4 BA,
                                                    • Sleeps 10
                                                      (4)
                                                      • 3 BR,
                                                      • 1 BA,
                                                      • 1 HF BA,
                                                      • Sleeps 6
                                                        1 Review
                                                        36 more choices from the HomeAway Network
                                                        3 night minimum stay
                                                        • 2 BR,
                                                        • 2 BA,
                                                        • 1 HF BA,
                                                        • Sleeps 4
                                                          (10)
                                                          Book it Now!
                                                          3 - 7 night minimum stay
                                                          • 3 BR,
                                                          • 3 BA,
                                                          • Sleeps 10
                                                            (5)
                                                            $2,002 - $4,004
                                                            per week
                                                            Book it Now!
                                                            7 night minimum stay
                                                            • 4 BR,
                                                            • 3 BA,
                                                            • Sleeps 10
                                                              (3)
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                                                              Recent Shelter Island Reviews

                                                              Gorgeous refuge

                                                              5 of 5
                                                              This place is a gem. The rooms are cozy and clean, but the best places to savor the property are the screened porch, the hammock, the Adirondack chairs facing the water, and dining in the converted garage with a view of the creek. We loved having access to the kayak and the grill, our kids loved the swing, and we rented bikes practically next door. Birders will love seeing ospreys that nest all over the island, the egrets gracing the creek, and all variety of smaller birds congregating at the feeders. The owner was gracious and exceedingly helpful; during our stay he responded promptly to our Qs about the property and places to visit on the island. I would definitely look into staying here again on our next visit to Shelter Island.
                                                              • Submitted: Aug 19, 2014
                                                              • Stayed: Jul 2014

                                                              Fantastic, Family Friendly, Well-Equipped Dream

                                                              5 of 5
                                                              This house was wonderful. The kitchen was fully equipped with spices, paper goods, sunscreen, bug spray -- everything you need but don't necessarily want to pack. The pool and hot tub were the focal attraction for our clan, but the screened in porch and ample supply of board games were very much appreciated. My girls loved the family of deer who visited twice daily, and the close proximity to town and beaches was also a hit. The owners are incredibly responsive and helpful. I cannot say enough good things about this place! I would only add: the Clam Chowder at SALT is the best on the island!
                                                              • Submitted: Aug 18, 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