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344 Houses

    24

    Romantic Shelter Island Cottage w/2 Pools & a Pond

    Shelter Island / Shelter Island Heights

    Shelter Island Heights cottage

    1 6 min stay varies

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

    Price per night from

    $441

    Responds fast!
    avg. 8 minutes

    Price per night from

    $441

      26

      Luxurious ‘Shelter Island Hideaway’ w/ Pool!

      Hamptons / Shelter Island

      Shelter Island house

      4 10 min stay varies

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

      Price per night from

      $567

      Responds fast!
      avg. 12 minutes

      Price per night from

      $567

      (2) Excellent 

        30

        WATERFRONT Estate on Shelter Island. Fully Renovated. 100 Ft DOCK

        Hamptons / Shelter Island

        Shelter Island house

        4 8 14 nights min

        • 4 bedrooms
        • sleeps 8
        • 14 nights min
        • Nearest beach 1 mi
        • Child Friendly
        • Air conditioning

        Price per night from

        $286

        Price per night from

        $286

          19

          Waterfront Charmer on idyllic Shelter Island

          Hamptons / Shelter Island

          Shelter Island house

          3 8 14 nights min

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

          Price per night from

          $1,063

          Price per night from

          $1,063

            49

            55 Shore

            Shelter Island / Shelter Island Heights

            Shelter Island Heights villa

            6 12 7 nights min

            • 6 bedrooms
            • sleeps 12
            • 7 nights min
            • Ask about children
            • Ask about pets

            Price per night from

            $3,996

            Responds fast!
            avg. 1 hour 49 minutes

            Price per night from

            $3,996

              24

              Fabulous Beach Getaway

              Hamptons / Shelter Island

              Shelter Island house

              3 6 min stay varies

              • 3 bedrooms
              • sleeps 6
              • min stay varies
              • Swimming pool
              • Ask about children
              • Air conditioning

              Price per night from

              $650

              Price per night from

              $650

              Great rentals within 20 miles that match your search

              Distance approx 11.43 km from Shelter Island

                24

                Spacious Amagansett Home w/ Pool - Walk to Beach!

                Hamptons / Amagansett

                Amagansett house

                6 12 7 nights min

                • 6 bedrooms
                • sleeps 12
                • 7 nights min
                • Swimming pool
                • Child Friendly
                • Air conditioning

                Price per night from

                $847

                Responds fast!
                avg. 58 minutes

                Price per night from

                $847

                Distance approx 5.27 km from Shelter Island

                  29

                  Sag Harbor Home w/Backyard-Access to Private Beach

                  Hamptons / Sag Harbor

                  Sag Harbor house

                  4 8 2 nights min

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

                  Price per night from

                  $858

                  Responds fast!
                  avg. 58 minutes

                  Price per night from

                  $858

                  Distance approx 12.41 km from Shelter Island

                  (1) Excellent 

                    26

                    North Fork cottage getaway with private beach

                    North Fork / Mattituck

                    Mattituck cottage

                    4 9 14 nights min

                    • 4 bedrooms
                    • sleeps 9
                    • 14 nights min
                    • Child Friendly
                    • Air conditioning

                    Price per night from

                    $311

                    Responds fast!
                    avg. 55 minutes

                    Price per night from

                    $311

                    Distance approx 10.13 km from Shelter Island

                      17

                      Charming Cottage

                      Hamptons / East Hampton

                      East Hampton cottage

                      1 4 1 night min

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

                      Price per night from

                      $173

                      Price per night from

                      $173

                      Distance approx 4.65 km from Shelter Island

                        34

                        Beach Cottage, Bring The Dog, Founders Landing Beach, Southold, North Fork, NY

                        North Fork / Southold

                        Southold house

                        2 4 5 nights min

                        • 2 bedrooms
                        • sleeps 4
                        • 5 nights min
                        • Nearest beach 1 mi
                        • Child Friendly
                        • Air conditioning

                        Price per night from

                        $400

                        Price per night from

                        $400

                        Distance approx 19.14 km from Shelter Island

                          12

                          Montauk Ocean View Retreat-Rental Registry #16-950

                          Hamptons / Montauk

                          Montauk house

                          4 8 14 nights min

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

                          Price per night from

                          $1,150

                          Price per night from

                          $1,150

                          Distance approx 11.39 km from Shelter Island

                            38

                            Amagansett Estate 5 Bedroom 60ft Pool

                            Hamptons / Amagansett

                            Amagansett villa

                            5 10 3 nights min

                            • 5 bedrooms
                            • sleeps 10
                            • 3 nights min
                            • Swimming pool
                            • Child Friendly
                            • Air conditioning

                            Price per night from

                            $1,378

                            Price per night from

                            $1,378

                            Distance approx 13.73 km from Shelter Island

                              7

                              SOUTHAMPTON VACATION HOME

                              Hamptons / Southampton

                              Southampton house

                              5 16 7 nights min

                              • 5 bedrooms
                              • sleeps 16
                              • 7 nights min
                              • Suitable for children age 5+
                              • Air conditioning
                              • Ask about pets

                              Price per night from

                              $1,471

                              Price per night from

                              $1,471

                              Distance approx 13.94 km from Shelter Island

                                9

                                Seahaven Resort Motel Unit 8

                                Hamptons / Southampton

                                Southampton hotel apartment

                                1 2 min stay varies

                                • 1 bedroom
                                • sleeps 2
                                • min stay varies
                                • Child Friendly
                                • Air conditioning

                                Price per night from

                                $171

                                Price per night from

                                $171

                                Distance approx 17.93 km from Shelter Island

                                  11

                                  Fantasy Bay Front Country French Villa

                                  Hamptons / Southampton

                                  Southampton villa

                                  6 12 14 nights min

                                  • 6 bedrooms
                                  • sleeps 12
                                  • 14 nights min
                                  • Beach / lakeside relaxation
                                  • Swimming pool
                                  • Child Friendly

                                  Price per night from

                                  $1,959

                                  Price per night from

                                  $1,959

                                  Distance approx 13.94 km from Shelter Island

                                    7

                                    Seahaven Resort Motel Unit 6

                                    Hamptons / Southampton

                                    Southampton hotel apartment

                                    1 2 1 night min

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

                                    Price per night from

                                    $171

                                    Price per night from

                                    $171

                                    Distance approx 13.94 km from Shelter Island

                                    (1) Excellent 

                                      4

                                      Seahaven Resort Motel Unit 1

                                      Hamptons / Southampton

                                      Southampton hotel apartment

                                      1 4 1 night min

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

                                      Price per night from

                                      $229

                                      Price per night from

                                      $229

                                      Distance approx 7.52 km from Shelter Island

                                        27

                                        NEW! Nassau Point Home in Long Island Wine Country

                                        North Fork / Cutchogue

                                        Cutchogue house

                                        3 10 min stay varies

                                        • 3 bedrooms
                                        • sleeps 10
                                        • min stay varies
                                        • Child Friendly
                                        • Air conditioning

                                        Price per night from

                                        $276

                                        Responds fast!
                                        avg. 21 minutes

                                        Price per night from

                                        $276

                                        Distance approx 12.71 km from Shelter Island

                                          17

                                          Southampton Village Charmer with New Heated Pool

                                          Hamptons / Southampton

                                          Southampton house

                                          4 9 7 nights min

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

                                          Price per night from

                                          $1,722

                                          Price per night from

                                          $1,722

                                          Distance approx 19.56 km from Shelter Island

                                            11

                                            Mid Century Beach Bungalow Walk to Private Beach

                                            Hamptons / Montauk

                                            Montauk house

                                            2 6 14 nights min

                                            • 2 bedrooms
                                            • sleeps 6
                                            • 14 nights min
                                            • Child Friendly

                                            Price per night from

                                            $431

                                            Price per night from

                                            $431

                                            Distance approx 10.25 km from Shelter Island

                                              24

                                              Elegance,Privacy, French Farm House

                                              Hamptons / East Hampton

                                              East Hampton farmhouse

                                              3 8 30 nights min

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

                                              Price per night from

                                              $744

                                              Price per night from

                                              $744

                                              Distance approx 6.38 km from Shelter Island

                                                10

                                                East Hampton shingle style home

                                                Hamptons / East Hampton

                                                East Hampton house

                                                3 6 4 nights min

                                                • 3 bedrooms
                                                • sleeps 6
                                                • 4 nights min
                                                • Beach / lakeside relaxation
                                                • Nearest beach 0.05 mi
                                                • Child Friendly

                                                Price per night from

                                                $858

                                                Price per night from

                                                $858

                                                Distance approx 17.11 km from Shelter Island

                                                  23

                                                  Modern Hampton Bays House w/Pool & Beach Rights!

                                                  Southampton / Hampton Bays

                                                  Hampton Bays house

                                                  6 12 min stay varies

                                                  • 6 bedrooms
                                                  • sleeps 12
                                                  • min stay varies
                                                  • Swimming pool
                                                  • Child Friendly
                                                  • Air conditioning

                                                  Price per night from

                                                  $475

                                                  Responds fast!
                                                  avg. 58 minutes

                                                  Price per night from

                                                  $475

                                                  Distance approx 19 km from Shelter Island

                                                    6

                                                    4 BDR Montauk Home available weekly Oceanfront

                                                    Hamptons / Montauk

                                                    Montauk house

                                                    5 12 7 nights min

                                                    • 5 bedrooms
                                                    • sleeps 12
                                                    • 7 nights min
                                                    • Child Friendly
                                                    • Air conditioning
                                                    • Pet Friendly

                                                    Price per night from

                                                    $2,214

                                                    Price per night from

                                                    $2,214

                                                    Distance approx 4.4 km from Shelter Island

                                                      13

                                                      "This must be the place"

                                                      North Fork / Greenport

                                                      Greenport house

                                                      3 6 14 nights min

                                                      • 3 bedrooms
                                                      • sleeps 6
                                                      • 14 nights min
                                                      • Child Friendly
                                                      • Air conditioning
                                                      • Private garden

                                                      Price per night from

                                                      $528

                                                      Price per night from

                                                      $528

                                                      Distance approx 9.98 km from Shelter Island

                                                      (1)  

                                                        23

                                                        Hampton Accommodations 3 / FREE BIKE RENTALS

                                                        Hamptons / East Hampton

                                                        East Hampton b and b

                                                        1 2 min stay varies

                                                        • 1 bedroom
                                                        • sleeps 2
                                                        • min stay varies
                                                        • Beach / lakeside relaxation
                                                        • Nearest beach 2 mi

                                                        Price per night from

                                                        $287

                                                        Responds fast!
                                                        avg. 2 hours 0 minutes

                                                        Price per night from

                                                        $287

                                                        Distance approx 4.82 km from Shelter Island

                                                          24

                                                          East Marion Home Walk to Beach-3 Mi to Greenport!

                                                          North Fork / East Marion

                                                          East Marion house

                                                          3 8 min stay varies

                                                          • 3 bedrooms
                                                          • sleeps 8
                                                          • min stay varies
                                                          • Child Friendly
                                                          • Air conditioning

                                                          Price per night from

                                                          $258

                                                          Responds fast!
                                                          avg. 58 minutes

                                                          Price per night from

                                                          $258

                                                          Distance approx 4.56 km from Shelter Island

                                                          (1) Excellent 

                                                            35

                                                            The Victorian Seasons Cape

                                                            North Fork / East Marion

                                                            East Marion cottage

                                                            3 5 1 night min

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

                                                            Price per night from

                                                            $574

                                                            Price per night from

                                                            $574

                                                            Distance approx 19.82 km from Shelter Island

                                                              17

                                                              Montauk Beach Bungalow

                                                              Hamptons / Montauk

                                                              Montauk house

                                                              2 4 14 nights min

                                                              • 2 bedrooms
                                                              • sleeps 4
                                                              • 14 nights min
                                                              • Child Friendly
                                                              • Air conditioning
                                                              • Pet Friendly

                                                              Price per night from

                                                              $459

                                                              Responds fast!
                                                              avg. 29 minutes

                                                              Price per night from

                                                              $459

                                                              Distance approx 4.92 km from Shelter Island

                                                                8

                                                                Elegant Restored Sea Captain House

                                                                Hamptons / East Hampton

                                                                East Hampton house

                                                                2 4 14 nights min

                                                                • 2 bedrooms
                                                                • sleeps 4
                                                                • 14 nights min
                                                                • Child Friendly

                                                                Price per night from

                                                                $738

                                                                Price per night from

                                                                $738

                                                                Distance approx 13.22 km from Shelter Island

                                                                (1) Excellent 

                                                                  20

                                                                  Gorgeous House in Amagansett on Private Beach

                                                                  Hamptons / Amagansett

                                                                  Amagansett house

                                                                  4 8 30 nights min

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

                                                                  Price per night from

                                                                  $2,487

                                                                  Price per night from

                                                                  $2,487

                                                                  Distance approx 15.34 km from Shelter Island

                                                                  (9) Excellent 

                                                                    17

                                                                    Great Rates in 2019- No Increases In Rates and Over Holiday Weeks

                                                                    Southampton / Hampton Bays

                                                                    Hampton Bays house

                                                                    3 6 min stay varies

                                                                    • 3 bedrooms
                                                                    • sleeps 6
                                                                    • min stay varies
                                                                    • Beach / lakeside relaxation
                                                                    • Nearest beach 2 mi
                                                                    • Child Friendly
                                                                    “Hamptons” Dear Jackie and al, we had a wonderful time in your house. The service was perfect. We had everything in the house we needed. It is a in nice area . There are shops and restaurants near by. Thanks for everything Ina and family
                                                                    …see more

                                                                    Price per night from

                                                                    $303

                                                                    Price per night from

                                                                    $303

                                                                    Distance approx 7.81 km from Shelter Island

                                                                    (1) Excellent 

                                                                      38

                                                                      Tropical Paradise-Minimum 2 wk rental -rates reduced

                                                                      Hamptons / East Hampton

                                                                      East Hampton house

                                                                      4 8 30 nights min

                                                                      • 4 bedrooms
                                                                      • sleeps 8
                                                                      • 30 nights min
                                                                      • Child Friendly

                                                                      Price per night from

                                                                      $383

                                                                      Price per night from

                                                                      $383

                                                                      Distance approx 4.75 km from Shelter Island

                                                                        39

                                                                        The Seashell House

                                                                        Hamptons / Sag Harbor

                                                                        Sag Harbor house

                                                                        4 10 90 nights min

                                                                        • 4 bedrooms
                                                                        • sleeps 10
                                                                        • 90 nights min
                                                                        • Beach / lakeside relaxation
                                                                        • Child Friendly
                                                                        • Pet Friendly

                                                                        Price per night from

                                                                        $976

                                                                        Price per night from

                                                                        $976

                                                                        Distance approx 4.71 km from Shelter Island

                                                                          21

                                                                          Private Waterfront W Beach, New Renovation

                                                                          North Fork / Southold

                                                                          Southold house

                                                                          3 8 7 nights min

                                                                          • 3 bedrooms
                                                                          • sleeps 8
                                                                          • 7 nights min
                                                                          • Beach / lakeside relaxation
                                                                          • Nearest beach 0.25 mi
                                                                          • Ask about children

                                                                          Price per night from

                                                                          $603

                                                                          Price per night from

                                                                          $603

                                                                          Distance approx 9 km from Shelter Island

                                                                          (4) Excellent 

                                                                            17

                                                                            Bridgehampton South, Village Gem. Location, Location, Location!

                                                                            Hamptons / Bridgehampton

                                                                            Bridgehampton house

                                                                            3 6 min stay varies

                                                                            • 3 bedrooms
                                                                            • sleeps 6
                                                                            • min stay varies
                                                                            • Swimming pool
                                                                            • Ask about children
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $798

                                                                            Price per night from

                                                                            $798

                                                                            Distance approx 19.36 km from Shelter Island

                                                                              18

                                                                              MONTAUK COTTAGE NEAR THE SEA

                                                                              Hamptons / Montauk

                                                                              Montauk cottage

                                                                              2 4 30 nights min

                                                                              • 2 bedrooms
                                                                              • sleeps 4
                                                                              • 30 nights min
                                                                              • Child Friendly
                                                                              • Pet Friendly

                                                                              Price per night from

                                                                              $383

                                                                              Price per night from

                                                                              $383