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Shelter Island Vacation Rentals with Online Booking(24)

24 Results
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7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
    Book it Now!
    3 - 14 night minimum stay
    • 4 BR,
    • 4 BA,
    • 1 HF BA,
    • Sleeps 10
      Book it Now!
      14 - 30 night minimum stay
      • 3 BR,
      • 2 BA,
      • Sleeps 8
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        • 6 BR,
        • 4 BA,
        • Sleeps 14
          2 Reviews
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          2 - 3 night minimum stay
          • 6 BR,
          • 7 BA,
          • Sleeps 14
            (7)
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            • 5 BR,
            • 3 BA,
            • Sleeps 10
              $2,275 - $3,500
              per week
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              7 night minimum stay
              • 3 BR,
              • 2 BA,
              • Sleeps 6
                (3)
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                3 night minimum stay
                • 3 BR,
                • 2 BA,
                • 1 HF BA,
                • Sleeps 8
                  2 Reviews
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                  3 night minimum stay
                  • 2 BR,
                  • 2 BA,
                  • Sleeps 4
                    Book it Now!
                    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
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                        6 - 28 night minimum stay
                        • 3 BR,
                        • 2 BA,
                        • Sleeps 8
                          1 Review
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                          7 night minimum stay
                          • 3 BR,
                          • 3 BA,
                          • Sleeps 7
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                            • 2 BR,
                            • 2 BA,
                            • Sleeps 6
                              $3,500 - $3,850
                              per week
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                              14 - 30 night minimum stay
                              • 4 BR,
                              • 3 BA,
                              • Sleeps 8
                                9 more choices from the HomeAway Network
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                                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)
                                    Book it Now!
                                    4 night minimum stay
                                    • 3 BR,
                                    • 2 BA,
                                    • Sleeps 5
                                      (3)
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                                      1 - 5 night minimum stay
                                      • 4 BR,
                                      • 3 BA,
                                      • Sleeps 8
                                        1 Review
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                                        7 - 14 night minimum stay
                                        • 2 BR,
                                        • 1 BA,
                                        • Sleeps 6
                                          2 Reviews
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                                          • 4 BR,
                                          • 4 BA,
                                          • 1 HF BA,
                                          • Sleeps 10
                                            Book it Now!
                                            7 night minimum stay
                                            • 5 BR,
                                            • 3 BA,
                                            • 1 HF BA,
                                            • Sleeps 12
                                              Book it Now!
                                              2 - 7 night minimum stay
                                              • 3 BR,
                                              • Sleeps 5
                                                $1,700
                                                per week
                                                Book it Now!
                                                7 night minimum stay
                                                • 3 BR,
                                                • 2 BA,
                                                • Sleeps 6
                                                  1 Review
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                                                  Recent Shelter Island Reviews

                                                  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

                                                  Stunning, fabulous location, GREAT HOUSE

                                                  5 of 5
                                                  What can I say except I am VERY picky when it comes to rental homes and this property is even better in person than any picture would do it justice, and it hands down beat my high expectations. Each room has been decorated in stunning furnishings, lighting, the right balance of classic and modern. The screened in porch was a great place to start the day with coffee and baked goods purchased on the island, and NOTHING beats getting on the ferry for the short crossing, its like all the stress goes away. I will for sure be renting this property again!
                                                  • Submitted: May 6, 2014
                                                  • Stayed: May 2014