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  • Showing 101-150 of 300+
Additional fees apply. Taxes may be added.
    Wonderful! 4.8/5
    (6 reviews)
    avg/night
    • 3 BR
    • 1 BA
    • Sleeps 5
    Cottage #3783352
    6
      • 3 BR
      • 1 BA
      • Sleeps 7
      House #3800514
      1
        Exceptional! 5.0/5
        (15 reviews)
        avg/night
        • 2 BR
        • 2 BA
        • Sleeps 5
        Cottage #3903339
        15
        Viewed 9 times in the last 48 hours
          • 3 BR
          • 2 BA
          • Sleeps 6
          House #4216807
          1
            • 3 BR
            • 2 BA
            • Sleeps 6
            House #913403vb
              avg/night
              • 3 BR
              • 2 BA
              • 1 HF BA
              • Sleeps 4
              Cottage #450240vb
              1
              Viewed 15 times in the last 48 hours
                Exceptional! 5.0/5
                (9 reviews)
                $79
                avg/night
                • 1 BR
                • 1 BA
                • Sleeps 2
                Cottage #602111vb
                9
                Viewed 11 times in the last 48 hours
                  • 4 BR
                  • 5 BA
                  • Sleeps 10
                  House #3730764
                  2
                  Viewed 8 times in the last 48 hours
                    Wonderful! 4.8/5
                    (6 reviews)
                    avg/night
                    • 3 BR
                    • 2 BA
                    • Sleeps 8
                    House #482861vb
                    6
                      avg/night
                      • 4 BR
                      • 4 BA
                      • Sleeps 8
                      House #913835vb
                      3
                      Viewed 16 times in the last 48 hours
                        • 4 BR
                        • 2 BA
                        • Sleeps 9
                        Chateau / Country House #426081vb
                        4
                          • 3 BR
                          • 1 BA
                          • Sleeps 6
                          Cottage #4247665
                            Exceptional! 5.0/5
                            (19 reviews)
                            avg/night
                            • 2 BR
                            • 1 BA
                            • Sleeps 4
                            Cottage #466174vb
                            19
                              Exceptional! 5.0/5
                              (35 reviews)
                              avg/night
                              • 2 BR
                              • 1 BA
                              • Sleeps 4
                              Cottage #966043
                              35
                              Viewed 9 times in the last 48 hours
                                • 3 BR
                                • 1 BA
                                • Sleeps 6
                                Cottage #365948vb
                                11
                                  Excellent! 4.3/5
                                  (6 reviews)
                                  avg/night
                                  • 5 BR
                                  • 3 BA
                                  • Sleeps 10
                                  House #3807604
                                  6
                                  Viewed 8 times in the last 48 hours
                                    • 4 BR
                                    • 4 BA
                                    • Sleeps 8
                                    House #4104501
                                    6
                                      • 4 BR
                                      • 4 BA
                                      • 1 HF BA
                                      • Sleeps 8
                                      House #868490vb
                                      3
                                        • 4 BR
                                        • 2 BA
                                        • Sleeps 6
                                        House #596959vb
                                        1
                                          Exceptional! 5.0/5
                                          (8 reviews)
                                          avg/night
                                          • 2 BR
                                          • 2 BA
                                          • Sleeps 4
                                          Cottage #727404vb
                                          8
                                          Viewed 5 times in the last 48 hours
                                            • 5 BR
                                            • 5 BA
                                            • Sleeps 14
                                            House #823485vb
                                            8
                                              • 5 BR
                                              • 4 BA
                                              • 2 HF BA
                                              • Sleeps 10
                                              House #802183vb
                                              4
                                                • 3 BR
                                                • 3 BA
                                                • Sleeps 6
                                                House #4154502
                                                1
                                                  Excellent! 4.7/5
                                                  (6 reviews)
                                                  avg/night
                                                  • 5 BR
                                                  • 4 BA
                                                  • Sleeps 8
                                                  House #719782vb
                                                  6
                                                  Viewed 17 times in the last 48 hours
                                                    • 3 BR
                                                    • 3 BA
                                                    • 1 HF BA
                                                    • Sleeps 6
                                                    House #724679vb
                                                    1
                                                      • 4 BR
                                                      • 3 BA
                                                      • 1 HF BA
                                                      • Sleeps 8
                                                      House #231392
                                                      14
                                                        Exceptional! 5.0/5
                                                        (5 reviews)
                                                        avg/night
                                                        • 4 BR
                                                        • 3 BA
                                                        • 1 HF BA
                                                        • Sleeps 10
                                                        House #35297vb
                                                        5
                                                        Viewed 7 times in the last 48 hours
                                                          Wonderful! 4.8/5
                                                          (8 reviews)
                                                          avg/night
                                                          • 7 BR
                                                          • 7 BA
                                                          • Sleeps 20
                                                          House #262053vb
                                                          8
                                                          Viewed 42 times in the last 48 hours
                                                            • 2 BR
                                                            • 1 BA
                                                            • 1 HF BA
                                                            • Sleeps 6
                                                            House #3013094
                                                            4
                                                              avg/night
                                                              • 5 BR
                                                              • 6 BA
                                                              • Sleeps 10
                                                              House #4170965
                                                              1
                                                              Viewed 15 times in the last 48 hours
                                                                Exceptional! 5.0/5
                                                                (11 reviews)
                                                                avg/night
                                                                • 4 BR
                                                                • 2 BA
                                                                • Sleeps 8
                                                                Cottage #365830vb
                                                                11
                                                                Viewed 16 times in the last 48 hours
                                                                  • 3 BR
                                                                  • 2 BA
                                                                  • Sleeps 9
                                                                  House #145634vb
                                                                  14
                                                                    Wonderful! 4.9/5
                                                                    (15 reviews)
                                                                    avg/night
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 7
                                                                    House #460785vb
                                                                    15
                                                                      Exceptional! 5.0/5
                                                                      (11 reviews)
                                                                      avg/night
                                                                      • 4 BR
                                                                      • 3 BA
                                                                      • 2 HF BA
                                                                      • Sleeps 8
                                                                      House #3813450
                                                                      11
                                                                      Viewed 6 times in the last 48 hours
                                                                        • 4 BR
                                                                        • 3 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 10
                                                                        House #557475vb
                                                                        1
                                                                          Exceptional! 5.0/5
                                                                          (5 reviews)
                                                                          avg/night
                                                                          • 4 BR
                                                                          • 4 BA
                                                                          • Sleeps 12
                                                                          House #602286vb
                                                                          5
                                                                            • 3 BR
                                                                            • 2 BA
                                                                            • Sleeps 3
                                                                            Cottage #860888vb
                                                                              • 4 BR
                                                                              • 3 BA
                                                                              • 2 HF BA
                                                                              • Sleeps 10
                                                                              House #847418vb
                                                                              2
                                                                                • 3 BR
                                                                                • 3 BA
                                                                                • Sleeps 7
                                                                                House #911699
                                                                                  • 4 BR
                                                                                  • 3 BA
                                                                                  • 1 HF BA
                                                                                  • Sleeps 10
                                                                                  House #891044vb
                                                                                  1
                                                                                    Exceptional! 5.0/5
                                                                                    (8 reviews)
                                                                                    avg/night
                                                                                    • 4 BR
                                                                                    • 3 BA
                                                                                    • Sleeps 8
                                                                                    House #585265vb
                                                                                    8
                                                                                    Viewed 9 times in the last 48 hours
                                                                                      • 3 BR
                                                                                      • 3 BA
                                                                                      • Sleeps 6
                                                                                      House #739960vb
                                                                                        • 4 BR
                                                                                        • 4 BA
                                                                                        • Sleeps 9
                                                                                        House #890149vb
                                                                                        1
                                                                                          • 5 BR
                                                                                          • 4 BA
                                                                                          • Sleeps 12
                                                                                          House #887824vb
                                                                                          Viewed 6 times in the last 48 hours
                                                                                            Wonderful! 4.9/5
                                                                                            (17 reviews)
                                                                                            avg/night
                                                                                            • 3 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 6
                                                                                            House #296870
                                                                                            17
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • 1 HF BA
                                                                                              • Sleeps 4
                                                                                              House #4219247
                                                                                                Exceptional! 5.0/5
                                                                                                (5 reviews)
                                                                                                avg/night
                                                                                                • 2 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 5
                                                                                                Cottage #4086603
                                                                                                5
                                                                                                Viewed 10 times in the last 48 hours
                                                                                                  • 4 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 9
                                                                                                  House #739564vb
                                                                                                    • 3 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 6
                                                                                                    House #878785vb
                                                                                                    Viewed 5 times in the last 48 hours
                                                                                                      • 4 BR
                                                                                                      • 4 BA
                                                                                                      • Sleeps 10
                                                                                                      House #738181vb
                                                                                                      2
                                                                                                      • 101 - 150 of 300+

                                                                                                      Shelter Island: Houses, Cottages & More | Page 3 (300+)

                                                                                                       

                                                                                                      Recent Shelter Island Reviews

                                                                                                      Fun, cozy cottage.

                                                                                                      5 of 5
                                                                                                      We enjoyed our stay at the cottage to attend an October wedding in East Hampton. The cottage was accurately reflected in the pictures and was clean and well maintained. The owner contacted us to make sure everything was satisfactory while we were there. We had no trouble finding the cottage, which is short drive from downtown East Hampton.
                                                                                                      • Submitted: Nov 20, 2016
                                                                                                      • Stayed: Oct 2016

                                                                                                      Beautiful beach-front getaway

                                                                                                      5 of 5
                                                                                                      We had a great fall weekend getaway here. The house was perfect for relaxing and enjoying the water view, and it was easy to buy some fresh seafood and of course a bottle of wine nearby for a homecooked dinner. The enclosed porch in the back is the perfect place to enjoy a cup of tea in the morning looking out at the waves, and the couch and chairs inside are incredibly comfortable for curling up with a book. The house is well-kept and tastefully decorated. Highly recommended!
                                                                                                      • Submitted: Nov 7, 2016
                                                                                                      • Stayed: Nov 2016

                                                                                                      Great for a Weekend Away

                                                                                                      4 of 5
                                                                                                      I recently booked this property for a girls' weekend. It's in a great location, making it easy to get to Downtown Sag Harbor and to the nearby vineyards. There's a lot of open space to sit and talk, and the kitchen is fantastic, if you want to cook. (We particularly liked the wine fridge.) Sadly, it was a rainy and cold weekend, so we were unable to take advantage of the pool and outdoor area.
                                                                                                      • Submitted: Oct 3, 2016
                                                                                                      • Stayed: Sep 2016