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 svg-report-flag
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!
  • Showing 1-50 of 300+
Additional fees apply. Taxes may be added.
    avg/night
    • 3 BR
    • 2 BA
    • Sleeps 7
    House #908170vb
    1 Review
    Viewed 29 times in the last 48 hours
      • 5 BR
      • 3 BA
      • Sleeps 10
      House #425548vb
      14
        Excellent! 4.6/5
        (7 reviews)
        avg/night
        • 3 BR
        • 2 BA
        • 1 HF BA
        • Sleeps 8
        House #3621885
        7
        Viewed 14 times in the last 48 hours
          Wonderful! 4.9/5
          (14 reviews)
          avg/night
          • 3 BR
          • 2 BA
          • Sleeps 5
          House #3554393
          14
          Viewed 15 times in the last 48 hours
            • 5 BR
            • 4 BA
            • 1 HF BA
            • Sleeps 6
            House #159174
            2 Reviews
              $95
              avg/night
              • 3 BR
              • 2 BA
              • Sleeps 6
              House #321313vb
              1 Review
              Viewed 10 times in the last 48 hours
                Exceptional! 5.0/5
                (8 reviews)
                avg/night
                • 3 BR
                • 1 BA
                • Sleeps 6
                House #694738vb
                8
                Viewed 12 times in the last 48 hours
                  avg/night
                  • 4 BR
                  • 4 BA
                  • 1 HF BA
                  • Sleeps 7
                  House #3757374
                  3
                  Viewed 8 times in the last 48 hours
                    avg/night
                    • 3 BR
                    • 2 BA
                    • Sleeps 6
                    House #698921vb
                    1 Review
                    Viewed 6 times in the last 48 hours
                      • 3 BR
                      • 2 BA
                      • Sleeps 6
                      House #803084vb
                        avg/night
                        • 3 BR
                        • 3 BA
                        • Sleeps 7
                        House #326053
                        2 Reviews
                        Viewed 6 times in the last 48 hours
                          Exceptional! 5.0/5
                          (5 reviews)
                          avg/night
                          • 5 BR
                          • 4 BA
                          • Sleeps 12
                          House #344072vb
                          5
                          Viewed 9 times in the last 48 hours
                            Exceptional! 5.0/5
                            (13 reviews)
                            avg/night
                            • 4 BR
                            • 2 BA
                            • 1 HF BA
                            • Sleeps 9
                            House #602844vb
                            13
                            Viewed 21 times in the last 48 hours
                              Wonderful! 4.9/5
                              (9 reviews)
                              avg/night
                              • 4 BR
                              • 3 BA
                              • 2 HF BA
                              • Sleeps 8
                              House #746110vb
                              9
                              Viewed 28 times in the last 48 hours
                                Exceptional! 5.0/5
                                (26 reviews)
                                avg/night
                                • 2 BR
                                • 1 BA
                                • Sleeps 4
                                House #239698vb
                                26
                                Viewed 20 times in the last 48 hours
                                  Exceptional! 5.0/5
                                  (5 reviews)
                                  avg/night
                                  • 3 BR
                                  • 1 BA
                                  • Sleeps 8
                                  House #3925407
                                  5
                                  Viewed 46 times in the last 48 hours
                                    • 3 BR
                                    • 2 BA
                                    • Sleeps 6
                                    Cottage #702619vb
                                    7
                                      • 4 BR
                                      • 2 BA
                                      • Sleeps 8
                                      House #3931482
                                      2 Reviews
                                      Viewed 11 times in the last 48 hours
                                        Exceptional! 5.0/5
                                        (8 reviews)
                                        avg/night
                                        • 4 BR
                                        • 2 BA
                                        • Sleeps 10
                                        House #446286vb
                                        8
                                        Viewed 13 times in the last 48 hours
                                          • 3 BR
                                          • 2 BA
                                          • Sleeps 6
                                          House #891646vb
                                            • 2 BR
                                            • 2 BA
                                            • Sleeps 4
                                            House #3596889
                                              Excellent! 4.7/5
                                              (10 reviews)
                                              avg/night
                                              • 4 BR
                                              • 3 BA
                                              • Sleeps 10
                                              House #476247vb
                                              10
                                                Exceptional! 5.0/5
                                                (19 reviews)
                                                avg/night
                                                • 3 BR
                                                • 2 BA
                                                • Sleeps 8
                                                Bungalow #804815vb
                                                19
                                                Viewed 26 times in the last 48 hours
                                                  Exceptional! 5.0/5
                                                  (5 reviews)
                                                  avg/night
                                                  • 5 BR
                                                  • 2 BA
                                                  • Sleeps 12
                                                  House #628856vb
                                                  5
                                                  Viewed 12 times in the last 48 hours
                                                    • 3 BR
                                                    • Sleeps 8
                                                    House #470387vb
                                                    2 Reviews
                                                      Wonderful! 4.9/5
                                                      (8 reviews)
                                                      avg/night
                                                      • 3 BR
                                                      • 3 BA
                                                      • Sleeps 10
                                                      House #305998vb
                                                      8
                                                      Viewed 12 times in the last 48 hours
                                                        • 4 BR
                                                        • 3 BA
                                                        • Sleeps 8
                                                        House #989574
                                                        4
                                                          • 2 BR
                                                          • 1 BA
                                                          • Sleeps 6
                                                          Cottage #597850vb
                                                          9
                                                            • 3 BR
                                                            • 2 BA
                                                            • Sleeps 6
                                                            Apartment #830564vb
                                                            Viewed 9 times in the last 48 hours
                                                              • 3 BR
                                                              • 2 BA
                                                              • Sleeps 8
                                                              House #676220vb
                                                              1 Review
                                                                • 3 BR
                                                                • 3 BA
                                                                • Sleeps 7
                                                                House #611940vb
                                                                1 Review
                                                                  avg/night
                                                                  • 4 BR
                                                                  • 1 BA
                                                                  • Sleeps 8
                                                                  House #3942991
                                                                  4
                                                                  Viewed 9 times in the last 48 hours
                                                                    • 4 BR
                                                                    • 2 BA
                                                                    • Sleeps 5
                                                                    House #474895vb
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Sleeps 6
                                                                      House #450883vb
                                                                      2 Reviews
                                                                        • 4 BR
                                                                        • 2 BA
                                                                        • Sleeps 8
                                                                        Cottage #556885vb
                                                                        1 Review
                                                                          • 4 BR
                                                                          • 2 BA
                                                                          • Sleeps 8
                                                                          House #857206vb
                                                                            • 3 BR
                                                                            • 2 BA
                                                                            • 1 HF BA
                                                                            • Sleeps 6
                                                                            House #90560vb
                                                                            2 Reviews
                                                                              • 5 BR
                                                                              • 3 BA
                                                                              • Sleeps 10
                                                                              House #3781403
                                                                              2 Reviews
                                                                              Viewed 5 times in the last 48 hours
                                                                                • 4 BR
                                                                                • 3 BA
                                                                                • Sleeps 8
                                                                                House #829820vb
                                                                                  • 4 BR
                                                                                  • 3 BA
                                                                                  • Sleeps 7
                                                                                  Chateau / Country House #4202867
                                                                                  1 Review
                                                                                    • 3 BR
                                                                                    • 3 BA
                                                                                    • Sleeps 6
                                                                                    House #885475vb
                                                                                      • 4 BR
                                                                                      • 3 BA
                                                                                      • Sleeps 8
                                                                                      Chateau / Country House #817980vb
                                                                                        • 4 BR
                                                                                        • 4 BA
                                                                                        • 1 HF BA
                                                                                        • Sleeps 10
                                                                                        House #573696vb
                                                                                          • 2 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 4
                                                                                          Cottage #3808711
                                                                                            • 3 BR
                                                                                            • 4 BA
                                                                                            • Sleeps 6
                                                                                            House #470694vb
                                                                                              • 3 BR
                                                                                              • 2 BA
                                                                                              • 1 HF BA
                                                                                              • Sleeps 6
                                                                                              House #894525vb
                                                                                                • 3 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 6
                                                                                                House #965493vb
                                                                                                  • 4 BR
                                                                                                  • 4 BA
                                                                                                  • Sleeps 11
                                                                                                  House #872415vb
                                                                                                    Excellent! 4.6/5
                                                                                                    (44 reviews)
                                                                                                    avg/night
                                                                                                    • 2 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 6
                                                                                                    Cottage #135387
                                                                                                    44
                                                                                                    Viewed 24 times in the last 48 hours
                                                                                                      Wonderful! 4.9/5
                                                                                                      (16 reviews)
                                                                                                      avg/night
                                                                                                      • 3 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 9
                                                                                                      House #622236vb
                                                                                                      16
                                                                                                      Viewed 23 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Shelter Island: Vacation Rentals (1,376)

                                                                                                       

                                                                                                      Recent Shelter Island Reviews

                                                                                                      Lovely Victorian Home

                                                                                                      4 of 5
                                                                                                      We recently had the pleasure of staying at the Victorian house in Shelter Island for a wedding in September. After a brief orientation we settled in, choosing bedrooms and spreading out .The house is absolutely charming and right across from the street is the water. The house is spacious indoor as well as outdoors. The beds were very comfortable. The layout of the house was very accommodating for different activities such as watching TV, reading, playing games etc. The Kitchen was very functional and spacious. The house also has s wonderful porch to enjoy the scenery while having coffee. It also has a huge backyard with a patio and grill. It’s an excellent place for families with children because of the fenced in property. There is parking for approximately 5 vehicles. There are some restaurants within walking distance and it’s a wonderful place to go for walks. Convenient to everything we wanted to see and do-including walking distance to the ferry, which made for an easy day trip to Greenpoint, NY and venture out to more restaurants, antique shops, wineries etc. The Wineries were absolutely wonderful! Wifi service was excellent. We would definitely stay here again. THANK YOU!
                                                                                                      • Submitted: Nov 6, 2016
                                                                                                      • Stayed: Sep 2016

                                                                                                      Beautifully curated, relaxing home

                                                                                                      5 of 5
                                                                                                      We had a relaxing stay with our extended family at this beautiful house and property over the summer. We took advantage of the lovely dock everyday with the in-house kayaks, canoe and paddleboard. Preparing meals in the chef's kitchen was a dream. We loved picking books out of the stocked library and enjoying the fresh air from the many sliding glass doors circulating over the designed open floor plan. All in all a fantastic getaway!
                                                                                                      • Submitted: Oct 10, 2016
                                                                                                      • Stayed: Aug 2016

                                                                                                      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