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

Close

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

317 Holiday homes

    24

    Holiday cottage with swimming pool in Shelter Island Heights

    Shelter Island / Shelter Island Heights

    1 6 min stay varies

    • 1 bedroom
    • sleeps 6
    • min stay varies
    • Swimming pool
    • Child friendly
    • Air conditioning

    from £338 / night

    £2,366 / week

    Book View

    Responds fast!
    avg. 33 minutes

    from £338 / 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 £259 / night

      £1,137 - £4,389 / week

      Book View

      from £259 / 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 £435 / night

        £3,042 / week

        Book View

        Responds fast!
        avg. 33 minutes

        from £435 / 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 £815 / night

          £5,705 / week

          Book View

          from £815 / night

            49

            Holiday villa in Shelter Island Heights

            Shelter Island / Shelter Island Heights

            6 12 min stay varies

            • 6 bedrooms
            • sleeps 12
            • min stay varies
            • Ask owner if suitable for children
            • Ask about pets

            from £3,067 / night

            £21,463 / week

            Book View

            Responds fast!
            avg. 48 minutes

            from £3,067 / night

            Great rentals within 20 miles that match your search

            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 £570 / night

              £3,986 / week

              Book View

              from £570 / night

              Distance approx 10.18 miles from Shelter Island

                11

                Holiday home in East Hampton

                Hamptons / East Hampton

                3 6 2 nights min

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

                from £784 / night

                £3,417 / week

                Book View

                Responds fast!
                avg. 27 minutes

                from £784 / night

                Distance approx 5.06 miles from Shelter Island

                  16

                  Holiday home in East Hampton

                  Hamptons / East Hampton

                  5 10 7 nights min

                  • 5 bedrooms
                  • sleeps 10
                  • 7 nights min
                  • Swimming pool
                  • Child friendly
                  • Air conditioning

                  from £1,227 / night

                  £8,585 / week

                  Book View

                  Responds fast!
                  avg. 2 hours 20 minutes

                  from £1,227 / 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 £219 / night

                    £1,314 - £2,541 / week

                    Book View

                    Responds fast!
                    avg. 2 hours 57 minutes

                    from £219 / night

                    Distance approx 8.65 miles from Shelter Island

                      14

                      Water Mill holiday home let

                      Hamptons / Water Mill

                      2 6 14 nights min

                      • 2 bedrooms
                      • sleeps 6
                      • 14 nights min
                      • Child friendly
                      • Pet friendly

                      from £701 / night

                      £4,906 / week

                      Book View

                      from £701 / night

                      Distance approx 11.05 miles from Shelter Island

                        28

                        Water Mill holiday home rental

                        Hamptons / Water Mill

                        6 12 30 nights min

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

                        from £729 / night

                        £5,099 / week

                        Book View

                        from £729 / night

                        Distance approx 16.79 miles from Shelter Island

                        (2) Very Good 

                          38

                          Holiday cottage in Clinton

                          Connecticut / Clinton

                          6 10 min stay varies

                          • 6 bedrooms
                          • sleeps 10
                          • min stay varies
                          • Beach / lakeside relaxation
                          • Child friendly
                          • Private garden

                          from £328 / night

                          £1,224 - £2,361 / week

                          Book View

                          Responds fast!
                          avg. 49 minutes

                          from £328 / night

                          Distance approx 8.96 miles from Shelter Island

                            11

                            Home rental in East Hampton with swimming pool

                            Hamptons / East Hampton

                            5 12 min stay varies

                            • 5 bedrooms
                            • sleeps 12
                            • min stay varies
                            • Swimming pool
                            • Child friendly
                            • Private garden

                            from £656 / night

                            £4,590 / week

                            Book View

                            from £656 / night

                            Distance approx 15.56 miles from Shelter Island

                              46

                              Holiday home in Hampton Bays

                              Southampton / Hampton Bays

                              4 10 14 nights min

                              • 4 bedrooms
                              • sleeps 10
                              • 14 nights min
                              • Swimming pool
                              • Ask owner if suitable for children
                              • Car not necessary

                              from £599 / night

                              £4,192 / week

                              Book View

                              from £599 / 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 £783 / night

                                £3,060 - £7,955 / week

                                Book View

                                from £783 / night

                                Distance approx 10.73 miles from Shelter Island

                                (1) Very Good 

                                  10

                                  Holiday home in Water Mill

                                  Hamptons / Water Mill

                                  3 6 30 nights min

                                  • 3 bedrooms
                                  • sleeps 6
                                  • 30 nights min
                                  • Beach / lakeside relaxation
                                  • Nearest beach 2 km
                                  • Child friendly

                                  from £595 / night

                                  £4,371 / week

                                  Book View

                                  from £595 / night

                                  Distance approx 14.86 miles from Shelter Island

                                    25

                                    Holiday home rental

                                    Southampton / Hampton Bays

                                    4 8 30 nights min

                                    • 4 bedrooms
                                    • sleeps 8
                                    • 30 nights min
                                    • Swimming pool
                                    • Air conditioning
                                    • Private garden

                                    from £437 / night

                                    £3,060 / week

                                    Book View

                                    from £437 / night

                                    Distance approx 12.54 miles from Shelter Island

                                      25

                                      Holiday home in Mattituck

                                      North Fork / Mattituck

                                      4 14 30 nights min

                                      • 4 bedrooms
                                      • sleeps 14
                                      • 30 nights min
                                      • Child friendly
                                      • Pet friendly

                                      from £1,312 / night

                                      £9,179 / week

                                      Book View

                                      from £1,312 / night

                                      Distance approx 13.22 miles from Shelter Island

                                      (1) Excellent 

                                        20

                                        Amagansett holiday home rental

                                        Hamptons / Amagansett

                                        4 8 30 nights min

                                        • 4 bedrooms
                                        • sleeps 8
                                        • 30 nights min
                                        • Beach / lakeside relaxation
                                        • Child friendly

                                        from £1,894 / night

                                        £13,258 / week

                                        Book View

                                        from £1,894 / night

                                        Distance approx 13.94 miles from Shelter Island

                                          6

                                          Holiday hotel apartment in Southampton

                                          Hamptons / Southampton

                                          1 4 1 night min

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

                                          from £201 / night

                                          £1,402 / week

                                          Book View

                                          from £201 / night

                                          Distance approx 13.94 miles from Shelter Island

                                            8

                                            Hotel apartment rental in Southampton

                                            Hamptons / Southampton

                                            1 2 1 night min

                                            • 1 bedroom
                                            • sleeps 2
                                            • 1 night min
                                            • Child friendly
                                            • Air conditioning

                                            from £262 / night

                                            £1,830 / week

                                            Book View

                                            from £262 / night

                                            Distance approx 8.93 miles from Shelter Island

                                              6

                                              Holiday home in East Hampton

                                              Hamptons / East Hampton

                                              3 10 7 nights min

                                              • 3 bedrooms
                                              • sleeps 10
                                              • 7 nights min
                                              • Beach / lakeside relaxation
                                              • Child friendly
                                              • Ask about pets

                                              from £500 / night

                                              £3,497 - £4,721 / week

                                              Book View

                                              from £500 / night

                                              Distance approx 3.81 miles from Shelter Island

                                                16

                                                Holiday farmhouse in Greenport

                                                North Fork / Greenport

                                                3 8 30 nights min

                                                • 3 bedrooms
                                                • sleeps 8
                                                • 30 nights min
                                                • Beach / lakeside relaxation
                                                • Child friendly
                                                • Car not necessary

                                                from £452 / night

                                                £3,162 / week

                                                Book View

                                                from £452 / night

                                                Distance approx 11.39 miles from Shelter Island

                                                  23

                                                  Holiday home in Amagansett

                                                  Hamptons / Amagansett

                                                  3 6 3 nights min

                                                  • 3 bedrooms
                                                  • sleeps 6
                                                  • 3 nights min
                                                  • Nearest beach 8 km
                                                  • Swimming pool
                                                  • Child friendly

                                                  from £787 / night

                                                  £5,507 / week

                                                  Book View

                                                  from £787 / night

                                                  Distance approx 9 miles from Shelter Island

                                                  (2) Excellent 

                                                    59

                                                    Holiday home with golf nearby in New Suffolk

                                                    North Fork / New Suffolk

                                                    4 8 14 nights min

                                                    • 4 bedrooms
                                                    • sleeps 8
                                                    • 14 nights min
                                                    • Child friendly

                                                    from £844 / night

                                                    £5,905 / week

                                                    Book View

                                                    from £844 / night

                                                    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 £657 / night

                                                      £4,599 / week

                                                      Book View

                                                      Responds fast!
                                                      avg. 24 minutes

                                                      from £657 / night

                                                      Distance approx 8.9 miles from Shelter Island

                                                      (1) Excellent 

                                                        36

                                                        Home rental in East Hampton

                                                        Hamptons / East Hampton

                                                        5 11 7 nights min

                                                        • 5 bedrooms
                                                        • sleeps 11
                                                        • 7 nights min
                                                        • Beach / lakeside relaxation
                                                        • Swimming pool
                                                        • Child friendly

                                                        from £1,249 / night

                                                        £8,742 / week

                                                        Book View

                                                        from £1,249 / night

                                                        Distance approx 15.35 miles from Shelter Island

                                                          7

                                                          Holiday villa rental

                                                          Connecticut / Old Saybrook

                                                          2 4 1 night min

                                                          • 2 bedrooms
                                                          • sleeps 4
                                                          • 1 night min
                                                          • Child friendly

                                                          from £700 / night

                                                          £4,900 / week

                                                          Book View

                                                          from £700 / 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 £564 / night

                                                            £3,942 / week

                                                            Book View

                                                            Responds fast!
                                                            avg. 1 hour 10 minutes

                                                            from £564 / night

                                                            Distance approx 13.94 miles from Shelter Island

                                                              8

                                                              Southampton holiday hotel apartment rental

                                                              Hamptons / Southampton

                                                              1 4 1 night min

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

                                                              from £183 / night

                                                              £1,282 / week

                                                              Book View

                                                              from £183 / night

                                                              Distance approx 9.99 miles from Shelter Island

                                                                11

                                                                Holiday home in Amagansett

                                                                Hamptons / Amagansett

                                                                4 10 2 nights min

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

                                                                from £2,190 / night

                                                                £8,760 / week

                                                                Book View

                                                                Responds fast!
                                                                avg. 3 hours 18 minutes

                                                                from £2,190 / night

                                                                Distance approx 7.28 miles from Shelter Island

                                                                  24

                                                                  Holiday cottage in Southampton

                                                                  Hamptons / Southampton

                                                                  3 8 3 nights min

                                                                  • 3 bedrooms
                                                                  • sleeps 8
                                                                  • 3 nights min
                                                                  • Beach / lakeside relaxation
                                                                  • Child friendly
                                                                  • Air conditioning

                                                                  from £828 / night

                                                                  £5,795 / week

                                                                  Book View

                                                                  from £828 / night

                                                                  Distance approx 13.94 miles from Shelter Island

                                                                  (1) Excellent 

                                                                    4

                                                                    Holiday hotel apartment in Southampton

                                                                    Hamptons / Southampton

                                                                    1 4 1 night min

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

                                                                    from £175 / night

                                                                    £1,221 / week

                                                                    Book View

                                                                    from £175 / 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 £117 / night

                                                                      £818 / week

                                                                      Book View

                                                                      from £117 / night

                                                                      Distance approx 9.3 miles from Shelter Island

                                                                        12

                                                                        Home rental in East Hampton

                                                                        Hamptons / East Hampton

                                                                        8 18 7 nights min

                                                                        • 8 bedrooms
                                                                        • sleeps 18
                                                                        • 7 nights min
                                                                        • Child friendly

                                                                        from £6,570 / night

                                                                        £45,987 / week

                                                                        Book View

                                                                        from £6,570 / night

                                                                        Distance approx 19.6 miles from Shelter Island

                                                                        (1) Excellent 

                                                                          10

                                                                          Holiday home rental

                                                                          Hamptons / Montauk

                                                                          5 9 7 nights min

                                                                          • 5 bedrooms
                                                                          • sleeps 9
                                                                          • 7 nights min
                                                                          • Child friendly
                                                                          • Air conditioning
                                                                          • Private garden

                                                                          from £657 / night

                                                                          £4,730 / week

                                                                          Book View

                                                                          from £657 / night

                                                                          Distance approx 4.93 miles from Shelter Island

                                                                          (2) Excellent 

                                                                            14

                                                                            Holiday home rental

                                                                            Hamptons / Sag Harbor

                                                                            5 10 1 night min

                                                                            • 5 bedrooms
                                                                            • sleeps 10
                                                                            • 1 night min
                                                                            • Swimming pool
                                                                            • Child friendly
                                                                            • Air conditioning

                                                                            from £1,446 / night

                                                                            £7,884 / week

                                                                            Book View

                                                                            Responds fast!
                                                                            avg. 3 hours 24 minutes

                                                                            from £1,446 / night

                                                                            Distance approx 4.56 miles from Shelter Island

                                                                            (1) Excellent 

                                                                              35

                                                                              East Marion holiday cottage rental

                                                                              North Fork / East Marion

                                                                              3 5 1 night min

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

                                                                              from £438 / night

                                                                              £3,066 / week

                                                                              Book View

                                                                              from £438 / night

                                                                              Distance approx 14.45 miles from Shelter Island

                                                                              (8) Excellent 

                                                                                6

                                                                                Holiday home in Amagansett

                                                                                Hamptons / Amagansett

                                                                                2 8 7 nights min

                                                                                • 2 bedrooms
                                                                                • sleeps 8
                                                                                • 7 nights min
                                                                                • Child friendly
                                                                                • Pet friendly

                                                                                from £526 / night

                                                                                £3,679 / week

                                                                                Book View

                                                                                from £526 / night

                                                                                Distance approx 7.83 miles from Shelter Island

                                                                                  8

                                                                                  Holiday home rental

                                                                                  Hamptons / East Hampton

                                                                                  4 7 14 nights min

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

                                                                                  from £876 / night

                                                                                  £6,132 / week

                                                                                  Book View

                                                                                  from £876 / night

                                                                                  Also consider