Houses in Shelter Island and Villas – Holiday Lettings - Holiday Rentals Shelter Island

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321 Holiday homes

    24

    Holiday cottage with swimming pool in Shelter Island Heights

    Shelter Island / Shelter Island Heights

    2 6 min stay varies

    • 2 bedrooms
    • sleeps 6
    • min stay varies
    • Swimming pool
    • Child friendly
    • Air conditioning

    from £342 / night

    £2,389 / week

    Book View

    Responds fast!
    avg. 3 hours 43 minutes

    from £342 / night

    (2) Excellent 

      30

      Shelter Island holiday home rental

      Hamptons / Shelter Island

      4 8 14 nights min

      • 4 bedrooms
      • sleeps 8
      • 14 nights min
      • Nearest beach 1 km
      • Child friendly
      • Air conditioning

      from £262 / night

      £1,148 - £4,433 / week

      Book View

      from £262 / night

        26

        Shelter Island holiday home let

        Hamptons / Shelter Island

        4 10 min stay varies

        • 4 bedrooms
        • sleeps 10
        • min stay varies
        • Swimming pool
        • Child friendly
        • Air conditioning

        from £439 / night

        £3,072 / week

        Book View

        Responds fast!
        avg. 37 minutes

        from £439 / night

          19

          Shelter Island holiday home rental

          Hamptons / Shelter Island

          3 8 14 nights min

          • 3 bedrooms
          • sleeps 8
          • 14 nights min
          • Child friendly
          • Air conditioning
          • Private garden

          from £824 / night

          £5,762 / week

          Book View

          from £824 / night

            49

            Holiday villa in Shelter Island Heights

            Shelter Island / Shelter Island Heights

            6 12 7 nights min

            • 6 bedrooms
            • sleeps 12
            • 7 nights min
            • Ask owner if suitable for children
            • Ask about pets

            from £3,097 / night

            £21,678 / week

            Book View

            Responds fast!
            avg. 1 hour 1 minutes

            from £3,097 / night

            Great rentals within 20 miles that match your search

            Distance approx 5.27 miles from Shelter Island

              29

              Holiday home in Sag Harbor

              Hamptons / Sag Harbor

              4 8 2 nights min

              • 4 bedrooms
              • sleeps 8
              • 2 nights min
              • Child friendly
              • Air conditioning

              from £665 / night

              £4,654 / week

              Book View

              Responds fast!
              avg. 18 minutes

              from £665 / night

              Distance approx 10.08 miles from Shelter Island

              (1) Excellent 

                6

                East Hampton holiday home rental

                Hamptons / East Hampton

                2 4 min stay varies

                • 2 bedrooms
                • sleeps 4
                • min stay varies
                • Nearest beach 4 km
                • Swimming pool
                • Air conditioning

                from £222 / night

                £1,552 - £4,433 / week

                Book View

                from £222 / night

                Distance approx 4.3 miles from Shelter Island

                (11) Excellent 

                Certificate of Excellence

                  14

                  Holiday apartment in Greenport

                  North Fork / Greenport

                  2 6 min stay varies

                  • 2 bedrooms
                  • sleeps 6
                  • min stay varies
                  • Beach / lakeside relaxation
                  • Nearest beach 0 km
                  • Swimming pool

                  Certificate of Excellence

                  from £222 / night

                  £1,884 - £2,482 / week

                  Book View

                  Responds fast!
                  avg. 3 hours 42 minutes

                  from £222 / night

                  Distance approx 6.95 miles from Shelter Island

                    24

                    Home accommodation in Orient

                    North Fork / Orient

                    5 14 14 nights min

                    • 5 bedrooms
                    • sleeps 14
                    • 14 nights min
                    • Child friendly
                    • Air conditioning
                    • Private garden

                    from £843 / night

                    £5,895 / week

                    Book View

                    Responds fast!
                    avg. 2 hours 40 minutes

                    from £843 / night

                    Distance approx 16.46 miles from Shelter Island

                    (3) Excellent 

                      25

                      Home letting in Hampton Bays with swimming pool

                      Southampton / Hampton Bays

                      4 9 14 nights min

                      • 4 bedrooms
                      • sleeps 9
                      • 14 nights min
                      • Nearest beach 3 km
                      • Swimming pool
                      • Child friendly

                      from £577 / night

                      £3,103 - £3,723 / week

                      Book View

                      Responds fast!
                      avg. 2 hours 57 minutes

                      from £577 / night

                      Distance approx 10.13 miles from Shelter Island

                        17

                        Holiday cottage with shared pool in East Hampton

                        Hamptons / East Hampton

                        1 4 1 night min

                        • 1 bedroom
                        • sleeps 4
                        • 1 night min
                        • Swimming pool
                        • Child friendly
                        • Air conditioning

                        from £133 / night

                        £931 / week

                        Book View

                        from £133 / night

                        Distance approx 10.86 miles from Shelter Island

                          26

                          Holiday home with golf nearby in East Hampton

                          Hamptons / East Hampton

                          3 6 1 night min

                          • 3 bedrooms
                          • sleeps 6
                          • 1 night min
                          • Beach / lakeside relaxation
                          • Swimming pool
                          • Child friendly

                          from £1,951 / night

                          £11,081 / week

                          Book View

                          Responds fast!
                          avg. 18 minutes

                          from £1,951 / night

                          Distance approx 5.04 miles from Shelter Island

                          (6) Excellent 

                            14

                            Home rental in East Marion

                            North Fork / East Marion

                            4 8 7 nights min

                            • 4 bedrooms
                            • sleeps 8
                            • 7 nights min
                            • Child friendly
                            • Air conditioning
                            • Pet friendly

                            from £221 / night

                            £1,330 - £2,571 / week

                            Book View

                            from £221 / night

                            Distance approx 13.85 miles from Shelter Island

                              18

                              Holiday home in Southampton

                              Hamptons / Southampton

                              4 8 14 nights min

                              • 4 bedrooms
                              • sleeps 8
                              • 14 nights min
                              • Beach / lakeside relaxation
                              • Air conditioning
                              • Private garden

                              from £1,583 / night

                              £11,081 / week

                              Book View

                              from £1,583 / night

                              Distance approx 6.6 miles from Shelter Island

                                20

                                Holiday home in East Hampton

                                Hamptons / East Hampton

                                3 7 15 nights min

                                • 3 bedrooms
                                • sleeps 7
                                • 15 nights min
                                • Swimming pool
                                • Child friendly
                                • Air conditioning

                                from £824 / night

                                £5,762 / week

                                Book View

                                from £824 / night

                                Distance approx 14.11 miles from Shelter Island

                                  13

                                  Holiday apartment in Mattituck

                                  North Fork / Mattituck

                                  5 14 2 nights min

                                  • 5 bedrooms
                                  • sleeps 14
                                  • 2 nights min
                                  • Beach / lakeside relaxation
                                  • Nearest beach 4 km
                                  • Ask owner if suitable for children

                                  from £794 / night

                                  £3,103 - £8,067 / week

                                  Book View

                                  from £794 / night

                                  Distance approx 4.62 miles from Shelter Island

                                  (3) Excellent 

                                    22

                                    Holiday cottage in East Marion

                                    North Fork / East Marion

                                    2 4 1 night min

                                    • 2 bedrooms
                                    • sleeps 4
                                    • 1 night min
                                    • Child friendly
                                    • Air conditioning
                                    • Private garden

                                    from £355 / night

                                    £2,039 / week

                                    Book View

                                    Responds fast!
                                    avg. 2 hours 41 minutes

                                    from £355 / night

                                    Distance approx 4.52 miles from Shelter Island

                                    (5) Excellent 

                                      23

                                      East Marion holiday cottage rental

                                      North Fork / East Marion

                                      2 4 1 night min

                                      • 2 bedrooms
                                      • sleeps 4
                                      • 1 night min
                                      • Child friendly
                                      • Air conditioning
                                      • Private garden

                                      from £355 / night

                                      £2,039 / week

                                      Book View

                                      Responds fast!
                                      avg. 2 hours 41 minutes

                                      from £355 / night

                                      Distance approx 19.14 miles from Shelter Island

                                        12

                                        Holiday home in Montauk

                                        Hamptons / Montauk

                                        4 8 14 nights min

                                        • 4 bedrooms
                                        • sleeps 8
                                        • 14 nights min
                                        • Beach / lakeside relaxation
                                        • Nearest beach 2 km
                                        • Child friendly

                                        from £887 / night

                                        £6,206 / week

                                        Book View

                                        from £887 / night

                                        Distance approx 4.43 miles from Shelter Island

                                          15

                                          Holiday home in Southold

                                          North Fork / Southold

                                          3 6 7 nights min

                                          • 3 bedrooms
                                          • sleeps 6
                                          • 7 nights min
                                          • Child friendly
                                          • Air conditioning
                                          • Private garden

                                          from £412 / night

                                          £2,881 / week

                                          Book View

                                          from £412 / night

                                          Distance approx 7.84 miles from Shelter Island

                                          (1) Excellent 

                                            14

                                            Peconic holiday cottage rental

                                            North Fork / Peconic

                                            3 6 14 nights min

                                            • 3 bedrooms
                                            • sleeps 6
                                            • 14 nights min
                                            • Beach / lakeside relaxation
                                            • Child friendly
                                            • Air conditioning

                                            from £380 / night

                                            £2,660 / week

                                            Book View

                                            from £380 / night

                                            Distance approx 7.26 miles from Shelter Island

                                            (6) Excellent 

                                              20

                                              Holiday home rental

                                              Hamptons / Southampton

                                              4 8 7 nights min

                                              • 4 bedrooms
                                              • sleeps 8
                                              • 7 nights min
                                              • Nearest beach 12 km
                                              • Swimming pool
                                              • Ask owner if suitable for children

                                              from £570 / night

                                              £3,989 / week

                                              Book View

                                              Responds fast!
                                              avg. 1 hour 10 minutes

                                              from £570 / night

                                              Distance approx 6.76 miles from Shelter Island

                                                24

                                                Holiday home with golf nearby in East Hampton

                                                Hamptons / East Hampton

                                                6 12 2 nights min

                                                • 6 bedrooms
                                                • sleeps 12
                                                • 2 nights min
                                                • Swimming pool
                                                • Child friendly
                                                • Air conditioning

                                                from £2,881 / night

                                                £20,167 / week

                                                Book View

                                                from £2,881 / night

                                                Distance approx 7.26 miles from Shelter Island

                                                (1) Excellent 

                                                  14

                                                  Holiday private room with shared pool in Southampton

                                                  Hamptons / Southampton

                                                  1 2 2 nights min

                                                  • 1 bedroom
                                                  • sleeps 2
                                                  • 2 nights min
                                                  • Nearest beach 12 km
                                                  • Swimming pool
                                                  • Air conditioning

                                                  from £222 / night

                                                  £1,552 / week

                                                  Book View

                                                  Responds fast!
                                                  avg. 1 hour 10 minutes

                                                  from £222 / night

                                                  Distance approx 8.25 miles from Shelter Island

                                                    29

                                                    East Hampton holiday home rental

                                                    Hamptons / East Hampton

                                                    3 6 14 nights min

                                                    • 3 bedrooms
                                                    • sleeps 6
                                                    • 14 nights min
                                                    • Swimming pool
                                                    • Air conditioning

                                                    from £339 / night

                                                    £2,371 / week

                                                    Book View

                                                    Responds fast!
                                                    avg. 18 minutes

                                                    from £339 / night

                                                    Distance approx 15.13 miles from Shelter Island

                                                      11

                                                      Holiday apartment in Hampton Bays

                                                      Southampton / Hampton Bays

                                                      1 4 13 nights min

                                                      • 1 bedroom
                                                      • sleeps 4
                                                      • 13 nights min
                                                      • Air conditioning
                                                      • Private garden

                                                      from £178 / night

                                                      £1,241 / week

                                                      Book View

                                                      from £178 / night

                                                      Distance approx 10.25 miles from Shelter Island

                                                        24

                                                        Holiday farmhouse in East Hampton

                                                        Hamptons / East Hampton

                                                        3 8 30 nights min

                                                        • 3 bedrooms
                                                        • sleeps 8
                                                        • 30 nights min
                                                        • Swimming pool
                                                        • Child friendly
                                                        • Air conditioning

                                                        from £577 / night

                                                        £4,034 / week

                                                        Book View

                                                        from £577 / night

                                                        Distance approx 4.56 miles from Shelter Island

                                                        (5) Excellent 

                                                          39

                                                          Holiday home in East Marion

                                                          North Fork / East Marion

                                                          5 9 1 night min

                                                          • 5 bedrooms
                                                          • sleeps 9
                                                          • 1 night min
                                                          • Child friendly
                                                          • Air conditioning
                                                          • Private garden

                                                          from £843 / night

                                                          £5,895 / week

                                                          Book View

                                                          Responds fast!
                                                          avg. 2 hours 41 minutes

                                                          from £843 / night

                                                          Distance approx 12.71 miles from Shelter Island

                                                            17

                                                            Holiday home in Southampton

                                                            Hamptons / Southampton

                                                            4 9 7 nights min

                                                            • 4 bedrooms
                                                            • sleeps 9
                                                            • 7 nights min
                                                            • Swimming pool
                                                            • Child friendly
                                                            • Air conditioning

                                                            from £1,330 / night

                                                            £9,308 / week

                                                            Book View

                                                            from £1,330 / night

                                                            Distance approx 9.98 miles from Shelter Island

                                                              17

                                                              Home rental in East Hampton

                                                              Hamptons / East Hampton

                                                              3 12 7 nights min

                                                              • 3 bedrooms
                                                              • sleeps 12
                                                              • 7 nights min
                                                              • Child friendly
                                                              • Air conditioning
                                                              • Pet friendly

                                                              from £317 / night

                                                              £2,217 / week

                                                              Book View

                                                              from £317 / night

                                                              Distance approx 5.21 miles from Shelter Island

                                                                33

                                                                Sag Harbor holiday home rental

                                                                Hamptons / Sag Harbor

                                                                4 10 min stay varies

                                                                • 4 bedrooms
                                                                • sleeps 10
                                                                • min stay varies
                                                                • Swimming pool
                                                                • Child friendly
                                                                • Air conditioning

                                                                from £732 / night

                                                                £5,120 / week

                                                                Book View

                                                                Responds fast!
                                                                avg. 18 minutes

                                                                from £732 / night

                                                                Distance approx 9.33 miles from Shelter Island

                                                                  22

                                                                  Holiday home in East Hampton

                                                                  Hamptons / East Hampton

                                                                  4 8 7 nights min

                                                                  • 4 bedrooms
                                                                  • sleeps 8
                                                                  • 7 nights min
                                                                  • Child friendly
                                                                  • Air conditioning
                                                                  • Private garden

                                                                  from £499 / night

                                                                  £3,192 / week

                                                                  Enquire View

                                                                  from £499 / night

                                                                  Distance approx 9.26 miles from Shelter Island

                                                                    11

                                                                    Home rental in East Hampton

                                                                    Hamptons / East Hampton

                                                                    8 16 7 nights min

                                                                    • 8 bedrooms
                                                                    • sleeps 16
                                                                    • 7 nights min
                                                                    • Swimming pool
                                                                    • Child friendly
                                                                    • Air conditioning

                                                                    from £6,649 / night

                                                                    £44,323 / week

                                                                    Book View

                                                                    from £6,649 / night

                                                                    Distance approx 16.31 miles from Shelter Island

                                                                      10

                                                                      Holiday home in Hampton Bays

                                                                      Southampton / Hampton Bays

                                                                      3 5 2 nights min

                                                                      • 3 bedrooms
                                                                      • sleeps 5
                                                                      • 2 nights min
                                                                      • Child friendly
                                                                      • Air conditioning
                                                                      • Pet friendly

                                                                      from £333 / night

                                                                      £1,951 / week

                                                                      Book View

                                                                      from £333 / night

                                                                      Distance approx 5.37 miles from Shelter Island

                                                                        18

                                                                        Holiday home letting

                                                                        Hamptons / Sag Harbor

                                                                        4 8 30 nights min

                                                                        • 4 bedrooms
                                                                        • sleeps 8
                                                                        • 30 nights min
                                                                        • Swimming pool
                                                                        • Child friendly
                                                                        • Car not necessary

                                                                        from £1,478 / night

                                                                        £10,342 / week

                                                                        Book View

                                                                        from £1,478 / night

                                                                        Distance approx 10.25 miles from Shelter Island

                                                                          24

                                                                          Holiday home in Springs

                                                                          Hamptons / Springs

                                                                          6 14 7 nights min

                                                                          • 6 bedrooms
                                                                          • sleeps 14
                                                                          • 7 nights min
                                                                          • Swimming pool
                                                                          • Child friendly
                                                                          • Air conditioning

                                                                          from £1,900 / night

                                                                          £13,297 / week

                                                                          Book View

                                                                          from £1,900 / night

                                                                          Distance approx 6.59 miles from Shelter Island

                                                                            13

                                                                            Home rental in East Hampton

                                                                            Hamptons / East Hampton

                                                                            4 8 90 nights min

                                                                            • 4 bedrooms
                                                                            • sleeps 8
                                                                            • 90 nights min
                                                                            • Beach / lakeside relaxation
                                                                            • Nearest beach 0.8 km
                                                                            • Swimming pool

                                                                            from £104 / night

                                                                            £724 / week

                                                                            Book View

                                                                            Responds fast!
                                                                            avg. 54 minutes

                                                                            from £104 / night

                                                                            Distance approx 8.23 miles from Shelter Island

                                                                              7

                                                                              Southampton holiday home rental

                                                                              Hamptons / Southampton

                                                                              4 10 14 nights min

                                                                              • 4 bedrooms
                                                                              • sleeps 10
                                                                              • 14 nights min
                                                                              • Swimming pool
                                                                              • Child friendly
                                                                              • Air conditioning

                                                                              from £710 / night

                                                                              £6,206 / week

                                                                              Book View

                                                                              from £710 / night

                                                                              Distance approx 13.94 miles from Shelter Island

                                                                                4

                                                                                Hotel apartment rental in Southampton

                                                                                Hamptons / Southampton

                                                                                1 4 1 night min

                                                                                • 1 bedroom
                                                                                • sleeps 4
                                                                                • 1 night min
                                                                                • Child friendly
                                                                                • Air conditioning

                                                                                from £186 / night

                                                                                £1,297 / week

                                                                                Book View

                                                                                from £186 / night

                                                                                Distance approx 4.67 miles from Shelter Island

                                                                                  41

                                                                                  East Marion holiday home rental

                                                                                  North Fork / East Marion

                                                                                  4 8 2 nights min

                                                                                  • 4 bedrooms
                                                                                  • sleeps 8
                                                                                  • 2 nights min
                                                                                  • Child friendly
                                                                                  • Air conditioning
                                                                                  • Private garden

                                                                                  from £577 / night

                                                                                  £3,546 / week

                                                                                  Book View

                                                                                  Responds fast!
                                                                                  avg. 2 hours 1 minutes

                                                                                  from £577 / night

                                                                                  Also consider