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2,367 Houses

    28

    246 Wianno Circle

    Cape Cod / Osterville

    Osterville house

    4 9 1 night min

    • 4 bedrooms
    • sleeps 9
    • 1 night min
    • Ask about children
    • Ask about pets

    Price per night from

    $428

    Price per night from

    $428

      28

      101 Carriage Road

      Cape Cod / Osterville

      Osterville house

      6 12 1 night min

      • 6 bedrooms
      • sleeps 12
      • 1 night min
      • Swimming pool
      • Ask about children
      • Pet Friendly

      Price per night from

      $3,571

      Price per night from

      $3,571

        21

        271 Eel River Road

        Cape Cod / Osterville

        Osterville house

        8 20 1 night min

        • 8 bedrooms
        • sleeps 20
        • 1 night min
        • Ask about children
        • Ask about pets

        Price per night from

        $1,875

        Price per night from

        $1,875

          19

          466 Parker Road

          Cape Cod / Osterville

          Osterville house

          3 6 1 night min

          • 3 bedrooms
          • sleeps 6
          • 1 night min
          • Ask about children
          • Pet Friendly

          Price per night from

          $257

          Price per night from

          $257

            12

            225 Wianno Circle

            Cape Cod / Osterville

            Osterville house

            3 6 1 night min

            • 3 bedrooms
            • sleeps 6
            • 1 night min
            • Ask about children
            • Ask about pets

            Price per night from

            $385

            Price per night from

            $385

              16

              260 Wianno Avenue

              Cape Cod / Osterville

              Osterville house

              6 10 1 night min

              • 6 bedrooms
              • sleeps 10
              • 1 night min
              • Ask about children
              • Pet Friendly

              Price per night from

              $642

              Price per night from

              $642

                43

                439 Sea View Avenue

                Cape Cod / Osterville

                Osterville house

                6 10 1 night min

                • 6 bedrooms
                • sleeps 10
                • 1 night min
                • Swimming pool
                • Ask about children
                • Ask about pets

                Price per night from

                $2,857

                Price per night from

                $2,857

                  4

                  Oyster Harbors Osterville Cape Cod

                  Cape Cod / Osterville

                  Osterville house

                  5 10 7 nights min

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

                  Price per night from

                  $737

                  Price per night from

                  $737

                    37

                    26 Cedar Lane

                    Cape Cod / Osterville

                    Osterville house

                    2 6 1 night min

                    • 2 bedrooms
                    • sleeps 6
                    • 1 night min
                    • Ask about children
                    • Ask about pets

                    Price per night from

                    $571

                    Price per night from

                    $571

                      12

                      Private Beachfront Estate in Oyster Harbors

                      Cape Cod / Osterville

                      Osterville house

                      6 12 7 nights min

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

                      Price per night from

                      $4,089

                      Price per night from

                      $4,089

                        24

                        77 Spice Lane

                        Cape Cod / Osterville

                        Osterville house

                        3 6 1 night min

                        • 3 bedrooms
                        • sleeps 6
                        • 1 night min
                        • Ask about children
                        • Ask about pets

                        Price per night from

                        $357

                        Price per night from

                        $357

                          14

                          44 Sunset Lane

                          Cape Cod / Osterville

                          Osterville house

                          3 6 1 night min

                          • 3 bedrooms
                          • sleeps 6
                          • 1 night min
                          • Ask about children
                          • Pet Friendly

                          Price per night from

                          $357

                          Price per night from

                          $357

                            35

                            146 Hollingsworth Road

                            Cape Cod / Osterville

                            Osterville house

                            4 8 1 night min

                            • 4 bedrooms
                            • sleeps 8
                            • 1 night min
                            • Ask about children
                            • Ask about pets

                            Price per night from

                            $428

                            Price per night from

                            $428

                              37

                              71 Sand Point Road

                              Cape Cod / Osterville

                              Osterville house

                              5 10 1 night min

                              • 5 bedrooms
                              • sleeps 10
                              • 1 night min
                              • Swimming pool
                              • Ask about children
                              • Ask about pets

                              Price per night from

                              $2,000

                              Price per night from

                              $2,000

                                25

                                77 Robbins Street

                                Cape Cod / Osterville

                                Osterville house

                                5 12 1 night min

                                • 5 bedrooms
                                • sleeps 12
                                • 1 night min
                                • Ask about children
                                • Ask about pets

                                Price per night from

                                $428

                                Price per night from

                                $428

                                  29

                                  Wonderful HIP HOME in OSTERVILLE! 134586

                                  Cape Cod / Osterville

                                  Osterville house

                                  3 8 7 nights min

                                  • 3 bedrooms
                                  • sleeps 8
                                  • 7 nights min
                                  • Child Friendly
                                  • Air conditioning

                                  Price per night from

                                  $200

                                  Price per night from

                                  $200

                                    19

                                    14 Indian Trail

                                    Cape Cod / Osterville

                                    Osterville house

                                    5 8 1 night min

                                    • 5 bedrooms
                                    • sleeps 8
                                    • 1 night min
                                    • Ask about children
                                    • Pet Friendly

                                    Price per night from

                                    $1,714

                                    Price per night from

                                    $1,714

                                    (1) Excellent 

                                      28

                                      NEAR the Village of Osterville & Dowses BEACH! 121868

                                      Cape Cod / Osterville

                                      Osterville house

                                      3 6 7 nights min

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

                                      Price per night from

                                      $221

                                      Price per night from

                                      $221

                                      (3) Excellent 

                                        26

                                        24 South Street

                                        Cape Cod / Osterville

                                        Osterville house

                                        4 8 1 night min

                                        • 4 bedrooms
                                        • sleeps 8
                                        • 1 night min
                                        • Ask about children
                                        • Pet Friendly

                                        Price per night from

                                        $285

                                        Price per night from

                                        $285

                                          31

                                          86 Leonard Road

                                          Cape Cod / Osterville

                                          Osterville house

                                          4 8 7 nights min

                                          • 4 bedrooms
                                          • sleeps 8
                                          • 7 nights min
                                          • Swimming pool
                                          • Ask about children
                                          • Ask about pets

                                          Price per night from

                                          $1,071

                                          Price per night from

                                          $1,071

                                            25

                                            21 Cockachoisett Lane

                                            Cape Cod / Osterville

                                            Osterville house

                                            4 8 1 night min

                                            • 4 bedrooms
                                            • sleeps 8
                                            • 1 night min
                                            • Ask about children
                                            • Pet Friendly

                                            Price per night from

                                            $457

                                            Price per night from

                                            $457

                                              14

                                              933 Main Street, #E

                                              Cape Cod / Osterville

                                              Osterville house

                                              2 4 1 night min

                                              • 2 bedrooms
                                              • sleeps 4
                                              • 1 night min
                                              • Ask about children
                                              • Ask about pets

                                              Price per night from

                                              $228

                                              Price per night from

                                              $228

                                                24

                                                92 Concord Lane

                                                Cape Cod / Osterville

                                                Osterville house

                                                3 8 1 night min

                                                • 3 bedrooms
                                                • sleeps 8
                                                • 1 night min
                                                • Ask about children
                                                • Pet Friendly

                                                Price per night from

                                                $250

                                                Price per night from

                                                $250

                                                  24

                                                  Seaside Osterville Colonial

                                                  Cape Cod / Osterville

                                                  Osterville house

                                                  3 9 2 nights min

                                                  • 3 bedrooms
                                                  • sleeps 9
                                                  • 2 nights min
                                                  • Child Friendly
                                                  • Air conditioning
                                                  • Private garden

                                                  Price per night from

                                                  $458

                                                  Price per night from

                                                  $458

                                                  (2) Excellent 

                                                    22

                                                    31 Eel River Road

                                                    Cape Cod / Osterville

                                                    Osterville house

                                                    4 10 1 night min

                                                    • 4 bedrooms
                                                    • sleeps 10
                                                    • 1 night min
                                                    • Ask about children
                                                    • Ask about pets

                                                    Price per night from

                                                    $571

                                                    Price per night from

                                                    $571

                                                    (1) Excellent 

                                                      19

                                                      94 Waterfield Road

                                                      Cape Cod / Osterville

                                                      Osterville house

                                                      4 8 1 night min

                                                      • 4 bedrooms
                                                      • sleeps 8
                                                      • 1 night min
                                                      • Ask about children
                                                      • Pet Friendly

                                                      Price per night from

                                                      $271

                                                      Price per night from

                                                      $271

                                                      (1) Excellent 

                                                        44

                                                        206 East Bay Road

                                                        Cape Cod / Osterville

                                                        Osterville house

                                                        5 8 1 night min

                                                        • 5 bedrooms
                                                        • sleeps 8
                                                        • 1 night min
                                                        • Ask about children
                                                        • Ask about pets

                                                        Price per night from

                                                        $1,142

                                                        Price per night from

                                                        $1,142

                                                        (1) Excellent 

                                                          64

                                                          405 Sea View Avenue

                                                          Cape Cod / Osterville

                                                          Osterville house

                                                          10 22 1 night min

                                                          • 10 bedrooms
                                                          • sleeps 22
                                                          • 1 night min
                                                          • Ask about children
                                                          • Ask about pets

                                                          Price per night from

                                                          $2,142

                                                          Price per night from

                                                          $2,142

                                                            23

                                                            Spacious Cape Cottage with English-Style Garden

                                                            Cape Cod / Osterville

                                                            Osterville house

                                                            3 7 7 nights min

                                                            • 3 bedrooms
                                                            • sleeps 7
                                                            • 7 nights min
                                                            • Nearest beach 0.32 mi
                                                            • Child Friendly
                                                            • Air conditioning

                                                            Price per night from

                                                            $236

                                                            Price per night from

                                                            $236

                                                              34

                                                              12 Cockachoiset Lane

                                                              Cape Cod / Osterville

                                                              Osterville house

                                                              3 8 1 night min

                                                              • 3 bedrooms
                                                              • sleeps 8
                                                              • 1 night min
                                                              • Ask about children
                                                              • Pet Friendly

                                                              Price per night from

                                                              $557

                                                              Price per night from

                                                              $557

                                                              (1) Very Good 

                                                                49

                                                                979 Sea View Avenue

                                                                Cape Cod / Osterville

                                                                Osterville house

                                                                11 20 1 night min

                                                                • 11 bedrooms
                                                                • sleeps 20
                                                                • 1 night min
                                                                • Ask about children
                                                                • Ask about pets

                                                                Price per night from

                                                                $1,571

                                                                Price per night from

                                                                $1,571

                                                                  51

                                                                  17 Indian Trail

                                                                  Cape Cod / Osterville

                                                                  Osterville house

                                                                  9 1 1 night min

                                                                  • 9 bedrooms
                                                                  • sleeps 1
                                                                  • 1 night min
                                                                  • Ask about children
                                                                  • Ask about pets

                                                                  Price per night from

                                                                  $3,571

                                                                  Price per night from

                                                                  $3,571

                                                                    18

                                                                    44 Wianno Circle

                                                                    Cape Cod / Osterville

                                                                    Osterville house

                                                                    4 8 1 night min

                                                                    • 4 bedrooms
                                                                    • sleeps 8
                                                                    • 1 night min
                                                                    • Ask about children
                                                                    • Ask about pets

                                                                    Price per night from

                                                                    $928

                                                                    Price per night from

                                                                    $928

                                                                      30

                                                                      31 Parker Road

                                                                      Cape Cod / Osterville

                                                                      Osterville house

                                                                      4 10 1 night min

                                                                      • 4 bedrooms
                                                                      • sleeps 10
                                                                      • 1 night min
                                                                      • Swimming pool
                                                                      • Ask about children
                                                                      • Ask about pets

                                                                      Price per night from

                                                                      $500

                                                                      Price per night from

                                                                      $500

                                                                      (1) Excellent 

                                                                        45

                                                                        344 Bridge Street

                                                                        Cape Cod / Osterville

                                                                        Osterville house

                                                                        4 9 1 night min

                                                                        • 4 bedrooms
                                                                        • sleeps 9
                                                                        • 1 night min
                                                                        • Ask about children
                                                                        • Ask about pets

                                                                        Price per night from

                                                                        $1,028

                                                                        Price per night from

                                                                        $1,028

                                                                          32

                                                                          Waterfront Home in Oyster Harbors - beach + dock

                                                                          Cape Cod / Osterville

                                                                          Osterville house

                                                                          4 8 7 nights min

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

                                                                          Price per night from

                                                                          $1,140

                                                                          Price per night from

                                                                          $1,140

                                                                            18

                                                                            83 Bunker Hill Road

                                                                            Cape Cod / Osterville

                                                                            Osterville house

                                                                            5 12 1 night min

                                                                            • 5 bedrooms
                                                                            • sleeps 12
                                                                            • 1 night min
                                                                            • Swimming pool
                                                                            • Ask about children
                                                                            • Ask about pets

                                                                            Price per night from

                                                                            $1,000

                                                                            Price per night from

                                                                            $1,000

                                                                              17

                                                                              271 Westwind Cir

                                                                              Cape Cod / Osterville

                                                                              Osterville house

                                                                              3 6 7 nights min

                                                                              • 3 bedrooms
                                                                              • sleeps 6
                                                                              • 7 nights min
                                                                              • Child Friendly
                                                                              • Pet Friendly

                                                                              Price per night from

                                                                              $122

                                                                              Price per night from

                                                                              $122