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343 Houses

    5

    Lakeside Cottage, Walk to Beach. Beautiful Sunsets

    North Fork / Southold

    Southold cottage

    2 4 14 nights min

    • 2 bedrooms
    • sleeps 4
    • 14 nights min
    • Beach / lakeside relaxation
    • Child Friendly
    • Pet Friendly

    Price per night from

    $344

    Price per night from

    $344

    (2) Excellent 

      17

      PRISTINE GETAWAY, WITHIN SHORT WALK OF TWO WHITE, SANDY, SOUND BEACHES

      North Fork / Southold

      Southold house

      3 6 14 nights min

      • 3 bedrooms
      • sleeps 6
      • 14 nights min
      • Beach / lakeside relaxation
      • Nearest beach 0.4 mi
      • Child Friendly

      Price per night from

      $430

      Price per night from

      $430

      (1) Excellent 

        19

        Beautiful Classic North Fork Home, large porch, pool, Jacuzzi, walk to beach

        North Fork / Southold

        Southold house

        3 6 7 nights min

        • 3 bedrooms
        • sleeps 6
        • 7 nights min
        • Nearest beach 0.8 mi
        • Swimming pool
        • Child Friendly

        Price per night from

        $458

        Price per night from

        $458

          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

          $399

          Price per night from

          $399

            15

            Southold Summer Home for rent

            North Fork / Southold

            Southold house

            3 6 7 nights min

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

            Price per night from

            $531

            Price per night from

            $531

              11

              Peaceful North Fork Escape - Special Spring and Summer Rates

              North Fork / Southold

              Southold house

              3 5 14 nights min

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

              Price per night from

              $287

              Price per night from

              $287

                24

                NEW! Waterfront Southhold Home w/ Sauna & Dock!

                North Fork / Southold

                Southold house

                2 6 14 nights min

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

                Price per night from

                $401

                Responds fast!
                avg. 7 minutes

                Price per night from

                $401

                  19

                  Southold Contemporary Summer Home Steps from Beach and Vineyard

                  North Fork / Southold

                  Southold house

                  3 6 14 nights min

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

                  Price per night from

                  $430

                  Price per night from

                  $430

                  (2) Excellent 

                    16

                    Beach House In Wine Country; walk to beach, large sun room, outdoor dining

                    North Fork / Southold

                    Southold cottage

                    2 4 7 nights min

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

                    Price per night from

                    $373

                    Price per night from

                    $373

                      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

                      $602

                      Price per night from

                      $602

                        24

                        Beach Front, spacious 5 Bedrooms, North Fork, Long Island

                        North Fork / Southold

                        Southold house

                        5 12 min stay varies

                        • 5 bedrooms
                        • sleeps 12
                        • min stay varies
                        • Child Friendly
                        • Air conditioning
                        • Private garden

                        Price per night from

                        $601

                        Price per night from

                        $601

                        (3) Excellent 

                          32

                          Shorecrest Beach House, 4 bedroom private beach front, new renovation

                          North Fork / Southold

                          Southold house

                          4 10 min stay varies

                          • 4 bedrooms
                          • sleeps 10
                          • min stay varies
                          • Beach / lakeside relaxation
                          • Ask about children
                          • Air conditioning

                          Price per night from

                          $572

                          Price per night from

                          $572

                            25

                            Founders Landing Saltwater Inground Heated Pool. Walk to Beach,Town, Restaurants

                            North Fork / Southold

                            Southold house

                            4 8 7 nights min

                            • 4 bedrooms
                            • sleeps 8
                            • 7 nights min
                            • Nearest beach 0.5 mi
                            • Swimming pool
                            • Child Friendly

                            Price per night from

                            $654

                            Price per night from

                            $654

                            Great rentals within 20 miles that match your search

                            Distance approx 5.98 km from Southold

                            (6) Excellent 

                              14

                              North Fork House with Private Beach Access

                              North Fork / East Marion

                              East Marion house

                              4 8 7 nights min

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

                              Price per night from

                              $284

                              Responds fast!
                              avg. 2 hours 57 minutes

                              Price per night from

                              $284

                              Distance approx 12.76 km from Southold

                                25

                                Shinnecock Hilltop Escape with Private Pool & Breathtaking Views

                                Southampton / Hampton Bays

                                Hampton Bays house

                                4 8 30 nights min

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

                                Price per night from

                                $568

                                Price per night from

                                $568

                                Distance approx 5.39 km from Southold

                                (2) Excellent 

                                  59

                                  Rare Waterfront Experience :: Forever Bay Vistas ::

                                  North Fork / New Suffolk

                                  New Suffolk house

                                  4 8 14 nights min

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

                                  Price per night from

                                  $1,096

                                  Price per night from

                                  $1,096

                                  Distance approx 14.03 km from Southold

                                  (1) Excellent 

                                    36

                                    East Hampton Luxury Home PERFECT FOR FAMILIES

                                    Hamptons / East Hampton

                                    East Hampton house

                                    5 11 7 nights min

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

                                    Price per night from

                                    $1,623

                                    Price per night from

                                    $1,623

                                    Distance approx 10.65 km from Southold

                                    (1) Excellent 

                                      16

                                      East Hampton/ Sag Harbor, 8 Acres, Pool, Tennis Ct, Hot tub, Sauna

                                      Hamptons / East Hampton

                                      East Hampton house

                                      5 8 7 nights min

                                      • 5 bedrooms
                                      • sleeps 8
                                      • 7 nights min
                                      • Nearest beach 7 mi
                                      • Swimming pool
                                      • Child Friendly

                                      Price per night from

                                      $1,350

                                      Responds fast!
                                      avg. 3 hours 31 minutes

                                      Price per night from

                                      $1,350

                                      Distance approx 17.59 km from Southold

                                        15

                                        Pristine Southampton Architect Home, Pool & Tennis

                                        Hamptons / East Quogue

                                        East Quogue house

                                        5 10 7 nights min

                                        • 5 bedrooms
                                        • sleeps 10
                                        • 7 nights min
                                        • Beach / lakeside relaxation
                                        • Nearest beach 5 mi
                                        • Swimming pool

                                        Price per night from

                                        $1,081

                                        Responds fast!
                                        avg. 2 hours 31 minutes

                                        Price per night from

                                        $1,081

                                        Distance approx 12.89 km from Southold

                                          34

                                          Shell House

                                          Southampton / Hampton Bays

                                          Hampton Bays house

                                          8 20 min stay varies

                                          • 8 bedrooms
                                          • sleeps 20
                                          • min stay varies
                                          • Beach / lakeside relaxation
                                          • Swimming pool
                                          • Child Friendly

                                          Price per night from

                                          $962

                                          Price per night from

                                          $962

                                          Distance approx 13.44 km from Southold

                                            14

                                            Beautiful East Hampton Home in Private Beach Community with Pool

                                            Hamptons / Springs

                                            Springs house

                                            5 10 7 nights min

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

                                            Price per night from

                                            $1,597

                                            Price per night from

                                            $1,597

                                            Distance approx 15.24 km from Southold

                                              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

                                              $171

                                              Responds fast!
                                              avg. 3 hours 53 minutes

                                              Price per night from

                                              $171

                                              Distance approx 13.27 km from Southold

                                                14

                                                Charmimg Beach cottage in Sagaponack

                                                Hamptons / Southampton

                                                Southampton house

                                                3 6 5 nights min

                                                • 3 bedrooms
                                                • sleeps 6
                                                • 5 nights min
                                                • Child Friendly
                                                • Pet Friendly
                                                • Private garden

                                                Price per night from

                                                $653

                                                Price per night from

                                                $653

                                                Distance approx 12.07 km from Southold

                                                  7

                                                  Private Suite in Contemporary Home

                                                  Hamptons / East Hampton

                                                  East Hampton house

                                                  1 2 1 night min

                                                  • 1 bedroom
                                                  • sleeps 2
                                                  • 1 night min
                                                  • Air conditioning
                                                  • Ask about pets

                                                  Price per night from

                                                  $455

                                                  Price per night from

                                                  $455

                                                  Distance approx 2.54 km from Southold Show on Map

                                                  (1) Excellent 

                                                    14

                                                    North Fork Beach House on LI Sound

                                                    North Fork / Peconic

                                                    Peconic cottage

                                                    3 6 14 nights min

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

                                                    Price per night from

                                                    $490

                                                    Price per night from

                                                    $490

                                                    Distance approx 17.21 km from Southold

                                                      16

                                                      Amagansett Summer Rental - Charming renovated Farmhouse with pool

                                                      Hamptons / Amagansett

                                                      Amagansett house

                                                      3 7 14 nights min

                                                      • 3 bedrooms
                                                      • sleeps 7
                                                      • 14 nights min
                                                      • Swimming pool
                                                      • Child Friendly
                                                      • Air conditioning

                                                      Price per night from

                                                      $1,011

                                                      Price per night from

                                                      $1,011

                                                      Distance approx 12.21 km from Southold

                                                        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

                                                        $1,467

                                                        Price per night from

                                                        $1,467

                                                        Distance approx 14.04 km from Southold

                                                          12

                                                          East Hampton Charmer

                                                          Hamptons / East Hampton

                                                          East Hampton house

                                                          3 6 30 nights min

                                                          • 3 bedrooms
                                                          • sleeps 6
                                                          • 30 nights min
                                                          • Child Friendly
                                                          • Air conditioning

                                                          Price per night from

                                                          $953

                                                          Price per night from

                                                          $953

                                                          Distance approx 12.02 km from Southold

                                                            10

                                                            Seahaven Resort Motel Unit 9

                                                            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

                                                            $239

                                                            Price per night from

                                                            $239

                                                            Distance approx 8.19 km from Southold

                                                              17

                                                              Cottage european charm private beach in Southampton, North Sea

                                                              Hamptons / Southampton

                                                              Southampton house

                                                              3 7 7 nights min

                                                              • 3 bedrooms
                                                              • sleeps 7
                                                              • 7 nights min
                                                              • Child Friendly

                                                              Price per night from

                                                              $539

                                                              Price per night from

                                                              $539

                                                              Distance approx 12.02 km from Southold

                                                                4

                                                                Seahaven Resort Motel Unit 2

                                                                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

                                                                $239

                                                                Price per night from

                                                                $239

                                                                Distance approx 14.42 km from Southold

                                                                (2) Very Good 

                                                                  38

                                                                  Charming 6 Bedroom Oceanfront Cottage By The Sea

                                                                  Connecticut / Clinton

                                                                  Clinton cottage

                                                                  6 10 min stay varies

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

                                                                  Price per night from

                                                                  $229

                                                                  Responds fast!
                                                                  avg. 50 minutes

                                                                  Price per night from

                                                                  $229

                                                                  Distance approx 13.69 km from Southold

                                                                  (14) Excellent 

                                                                  Certificate of Excellence

                                                                    26

                                                                    Hampton Bays, south of 27A

                                                                    Southampton / Hampton Bays

                                                                    Hampton Bays house

                                                                    4 8 2 nights min

                                                                    • 4 bedrooms
                                                                    • sleeps 8
                                                                    • 2 nights min
                                                                    • Beach / lakeside relaxation
                                                                    • Nearest beach 5 mi
                                                                    • Child Friendly

                                                                    Certificate of Excellence

                                                                    Price per night from

                                                                    $458

                                                                    Responds fast!
                                                                    avg. 2 hours 4 minutes

                                                                    Price per night from

                                                                    $458

                                                                    Distance approx 16.04 km from Southold

                                                                      15

                                                                      Walk to Beach, Contemporary, Amagansett, Eash Hamp

                                                                      Hamptons / East Hampton

                                                                      East Hampton house

                                                                      2 4 7 nights min

                                                                      • 2 bedrooms
                                                                      • sleeps 4
                                                                      • 7 nights min
                                                                      • Beach / lakeside relaxation
                                                                      • Air conditioning
                                                                      • Private garden

                                                                      Price per night from

                                                                      $735

                                                                      Responds fast!
                                                                      avg. 3 hours 50 minutes

                                                                      Price per night from

                                                                      $735

                                                                      Distance approx 13.4 km from Southold

                                                                        20

                                                                        Bright, White 4 Bed Contemporary in NW Woods on 2 Acres!

                                                                        Hamptons / East Hampton

                                                                        East Hampton house

                                                                        4 8 min stay varies

                                                                        • 4 bedrooms
                                                                        • sleeps 8
                                                                        • min stay varies
                                                                        • Swimming pool
                                                                        • Ask about children
                                                                        • Air conditioning

                                                                        Price per night from

                                                                        $450

                                                                        Price per night from

                                                                        $450

                                                                        Distance approx 11.7 km from Southold

                                                                          5

                                                                          Stunning Hamptons Contemporary

                                                                          Hamptons / Sagaponack

                                                                          Sagaponack house

                                                                          4 8 30 nights min

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

                                                                          Price per night from

                                                                          $1,524

                                                                          Price per night from

                                                                          $1,524

                                                                          Distance approx 14 km from Southold

                                                                            12

                                                                            Boaters Dream-Waterfront Summer Rental-Peconic Bay

                                                                            Hamptons / Southampton

                                                                            Southampton house

                                                                            4 8 30 nights min

                                                                            • 4 bedrooms
                                                                            • sleeps 8
                                                                            • 30 nights min
                                                                            • Beach / lakeside relaxation
                                                                            • Nearest beach 0.3 mi
                                                                            • Child Friendly

                                                                            Price per night from

                                                                            $648

                                                                            Price per night from

                                                                            $648

                                                                            Distance approx 15.78 km from Southold

                                                                              24

                                                                              *BRAND NEW* Hamptons Luxury — 5900sqf with Huge Backyard — Perfect for Families!

                                                                              Hamptons / East Quogue

                                                                              East Quogue house

                                                                              6 14 min stay varies

                                                                              • 6 bedrooms
                                                                              • sleeps 14
                                                                              • min stay varies
                                                                              • Swimming pool
                                                                              • Child Friendly
                                                                              • Air conditioning

                                                                              Price per night from

                                                                              $915

                                                                              Price per night from

                                                                              $915