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2,648 Houses

    4

    Topside MainHouse

    Cape Cod / South Orleans

    South Orleans house

    3 8 7 nights min

    • 3 bedrooms
    • sleeps 8
    • 7 nights min
    • Suitable for children age 5+

    Price per night from

    $1,220

    Price per night from

    $1,220

      41

      18 Scotlin Way Harwich Cape Cod

      Cape Cod / South Orleans

      South Orleans house

      3 8 min stay varies

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

      Price per night from

      $332

      Price per night from

      $332

        29

        Orleans Town Landing - 3906

        Cape Cod / South Orleans

        South Orleans house

        5 10 7 nights min

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

        Price per night from

        $257

        Price per night from

        $257

        (2) Excellent 

          10

          Topside BoatHouse on Pleasant Bay

          Cape Cod / South Orleans

          South Orleans boathouse

          2 4 7 nights min

          • 2 bedrooms
          • sleeps 4
          • 7 nights min
          • Ask about children
          • Private garden

          Price per night from

          $492

          Price per night from

          $492

          (1) Excellent 

            16

            Large House On Private Acre - Newly Remodeled & New Furnishings

            Cape Cod / South Orleans

            South Orleans house

            4 10 min stay varies

            • 4 bedrooms
            • sleeps 10
            • min stay varies
            • Child Friendly

            Price per night from

            $457

            Price per night from

            $457

              31

              Pleasant Bay Association Beach

              Cape Cod / South Orleans

              South Orleans house

              2 8 7 nights min

              • 2 bedrooms
              • sleeps 8
              • 7 nights min
              • Ask about children
              • Air conditioning
              • Pet Friendly

              Price per night from

              $279

              Price per night from

              $279

                28

                Exquisite Custom Built 5BR Home in Orleans: 004-OP

                Cape Cod / South Orleans

                South Orleans house

                5 12 min stay varies

                • 5 bedrooms
                • sleeps 12
                • min stay varies
                • Child Friendly

                Price per night from

                $719

                Price per night from

                $719

                  19

                  9 Woodridge Road 99912

                  Cape Cod / South Orleans

                  South Orleans house

                  4 8 7 nights min

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

                  Price per night from

                  $157

                  Price per night from

                  $157

                  (2) Very Good 

                    19

                    52 Forest Way 18423

                    Cape Cod / South Orleans

                    South Orleans house

                    5 8 7 nights min

                    • 5 bedrooms
                    • sleeps 8
                    • 7 nights min
                    • Child Friendly
                    • Air conditioning
                    “We enjoyed our rental very much.” This was the second year at this house. We enjoyed the house very much. It was clean and very well equiped. It met our needs, as a family, very well. There was plenty of room for all us. We have been coming to Cape Co
                    …see more

                    Price per night from

                    $200

                    Price per night from

                    $200

                      29

                      Waterfront Home with Large Private Deck and Hot Tub Overlooking Pond; 054-O

                      Cape Cod / South Orleans

                      South Orleans house

                      3 10 min stay varies

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

                      Price per night from

                      $308

                      Price per night from

                      $308

                        19

                        Waterview of Namequoit River

                        Cape Cod / South Orleans

                        South Orleans house

                        3 6 7 nights min

                        • 3 bedrooms
                        • sleeps 6
                        • 7 nights min
                        • Ask about children

                        Price per night from

                        $375

                        Price per night from

                        $375

                          18

                          Comfortable, Pet-Friendly Orleans Home

                          Cape Cod / South Orleans

                          South Orleans house

                          4 8 7 nights min

                          • 4 bedrooms
                          • sleeps 8
                          • 7 nights min
                          • Ask about children
                          • Air conditioning
                          • Pet Friendly

                          Price per night from

                          $179

                          Price per night from

                          $179

                          (1) Excellent 

                            36

                            Expansive Home by Orleans Town Landing

                            Cape Cod / South Orleans

                            South Orleans house

                            4 8 7 nights min

                            • 4 bedrooms
                            • sleeps 8
                            • 7 nights min
                            • Ask about children
                            • Air conditioning

                            Price per night from

                            $269

                            Price per night from

                            $269

                              28

                              Beautiful Luxury Home With Private Beach

                              Cape Cod / South Orleans

                              South Orleans house

                              4 8 7 nights min

                              • 4 bedrooms
                              • sleeps 8
                              • 7 nights min
                              • Ask about children
                              • Air conditioning
                              • Pet Friendly

                              Price per night from

                              $407

                              Price per night from

                              $407

                                11

                                Cape Cod Cottage in Nauset Village

                                Cape Cod / South Orleans

                                South Orleans house

                                3 6 7 nights min

                                • 3 bedrooms
                                • sleeps 6
                                • 7 nights min
                                • Ask about children
                                • Air conditioning

                                Price per night from

                                $208

                                Price per night from

                                $208

                                  43

                                  5 White Cedar Lane Orleans Cape Cod - White Cedar

                                  Cape Cod / South Orleans

                                  South Orleans house

                                  4 12 min stay varies

                                  • 4 bedrooms
                                  • sleeps 12
                                  • min stay varies
                                  • Child Friendly
                                  • Air conditioning

                                  Price per night from

                                  $613

                                  Price per night from

                                  $613

                                    56

                                    NEW LISTING! Beautiful home w/ entertainment - near golf courses & Pleasant Bay

                                    Cape Cod / South Orleans

                                    South Orleans house

                                    3 6 min stay varies

                                    • 3 bedrooms
                                    • sleeps 6
                                    • min stay varies
                                    • Child Friendly
                                    • Air conditioning

                                    Price per night from

                                    $134

                                    Responds fast!
                                    avg. 37 minutes

                                    Price per night from

                                    $134

                                      31

                                      Private Orleans Home on the Water

                                      Cape Cod / South Orleans

                                      South Orleans house

                                      4 8 7 nights min

                                      • 4 bedrooms
                                      • sleeps 8
                                      • 7 nights min
                                      • Ask about children

                                      Price per night from

                                      $407

                                      Price per night from

                                      $407

                                      Great rentals within 20 miles that match your search

                                      Distance approx 10.75 km from South Orleans

                                      (4) Very Good 

                                        8

                                        Cottage On River/walk Or Kayak[2] To Beach

                                        Dennis / Dennis Port

                                        Dennis Port cottage

                                        2 5 7 nights min

                                        • 2 bedrooms
                                        • sleeps 5
                                        • 7 nights min
                                        • Child Friendly
                                        • Air conditioning
                                        • Pet Friendly
                                        “Has a lot to like but needs a little help!” We enjoyed our stay and would like to go again. The river was a constant source of beauty and entertainment. I would suggest that the cleaners do a better job between renters. On first day we had long black
                                        …see more

                                        Price per night from

                                        $233

                                        Price per night from

                                        $233

                                        Distance approx 10.19 km from South Orleans

                                          13

                                          Family Friendly Cape Cod Rental Steps Away from Private Beach

                                          Dennis / Dennis Port

                                          Dennis Port house

                                          2 4 7 nights min

                                          • 2 bedrooms
                                          • sleeps 4
                                          • 7 nights min
                                          • Nearest beach 0.01 mi
                                          • Child Friendly
                                          • Air conditioning

                                          Price per night from

                                          $175

                                          Responds fast!
                                          avg. 3 hours 55 minutes

                                          Price per night from

                                          $175

                                          Distance approx 2.79 km from South Orleans Show on Map

                                          (11) Excellent 

                                            14

                                            Townhouse in Brewster, Ocean Edge Resort

                                            Cape Cod / Brewster

                                            Brewster house

                                            2 6 min stay varies

                                            • 2 bedrooms
                                            • sleeps 6
                                            • min stay varies
                                            • Beach / lakeside relaxation
                                            • Swimming pool
                                            • Child Friendly
                                            “Our new family tradition” We stayed in this townhouse for the past week and have already booked our stay for next year. My 2 year old daughter fell so in love with the place that by the end of our week, she was calling it, "Our Cape Cod home"! Booki
                                            …see more

                                            Price per night from

                                            $189

                                            Price per night from

                                            $189

                                            Distance approx 2.04 km from South Orleans Show on Map

                                              23

                                              Beautiful Cape Cod vacation home with brand new pool

                                              Orleans / East Orleans

                                              East Orleans house

                                              5 12 7 nights min

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

                                              Price per night from

                                              $2,082

                                              Price per night from

                                              $2,082

                                              Distance approx 17.7 km from South Orleans

                                                18

                                                Unique and Private 3 Bedroom in Truro

                                                Cape Cod / Truro

                                                Truro house

                                                3 8 7 nights min

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

                                                Price per night from

                                                $131

                                                Price per night from

                                                $131

                                                Distance approx 13.98 km from South Orleans

                                                  40

                                                  Beautiful high end home

                                                  Cape Cod / Yarmouth

                                                  Yarmouth house

                                                  2 6 7 nights min

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

                                                  Price per night from

                                                  $250

                                                  Price per night from

                                                  $250

                                                  Distance approx 11.67 km from South Orleans

                                                  (1) Excellent 

                                                    15

                                                    Charming Cape Cod Cottage by the Bay

                                                    Cape Cod / Dennis

                                                    Dennis cottage

                                                    4 8 min stay varies

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

                                                    Price per night from

                                                    $175

                                                    Responds fast!
                                                    avg. 1 hour 56 minutes

                                                    Price per night from

                                                    $175

                                                    Distance approx 11.45 km from South Orleans

                                                      9

                                                      Charming Beach House

                                                      Dennis / West Dennis

                                                      West Dennis house

                                                      4 10 7 nights min

                                                      • 4 bedrooms
                                                      • sleeps 10
                                                      • 7 nights min
                                                      • Child Friendly

                                                      Price per night from

                                                      $666

                                                      Price per night from

                                                      $666

                                                      Distance approx 11.15 km from South Orleans

                                                        32

                                                        Stunning water views and quality property in private location

                                                        Cape Cod / Yarmouth

                                                        Yarmouth house

                                                        4 10 7 nights min

                                                        • 4 bedrooms
                                                        • sleeps 10
                                                        • 7 nights min
                                                        • Swimming pool
                                                        • Child Friendly
                                                        • Private garden

                                                        Price per night from

                                                        $874

                                                        Price per night from

                                                        $874

                                                        Distance approx 7.19 km from South Orleans

                                                          4

                                                          Waterfront 3 Bedroom Eastham

                                                          Cape Cod / Eastham

                                                          Eastham house

                                                          3 6 min stay varies

                                                          • 3 bedrooms
                                                          • sleeps 6
                                                          • min stay varies
                                                          • Nearest beach 0 mi
                                                          • Child Friendly
                                                          • Car not necessary

                                                          Price per night from

                                                          $379

                                                          Price per night from

                                                          $379

                                                          Distance approx 14.62 km from South Orleans

                                                            17

                                                            Spacious Cape House close to beaches

                                                            Cape Cod / Barnstable

                                                            Barnstable house

                                                            4 10 7 nights min

                                                            • 4 bedrooms
                                                            • sleeps 10
                                                            • 7 nights min
                                                            • Child Friendly

                                                            Price per night from

                                                            $554

                                                            Price per night from

                                                            $554

                                                            Distance approx 9.72 km from South Orleans

                                                              21

                                                              Bayberry Lane

                                                              Cape Cod / South Dennis

                                                              South Dennis cottage

                                                              2 5 4 nights min

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

                                                              Price per night from

                                                              $321

                                                              Responds fast!
                                                              avg. 2 hours 29 minutes

                                                              Price per night from

                                                              $321

                                                              Distance approx 15.33 km from South Orleans

                                                                7

                                                                Summer Vacation Townhouse

                                                                Yarmouth / West Yarmouth

                                                                West Yarmouth apartment

                                                                1 4 7 nights min

                                                                • 1 bedroom
                                                                • sleeps 4
                                                                • 7 nights min
                                                                • Child Friendly

                                                                Price per night from

                                                                $210

                                                                Price per night from

                                                                $210

                                                                Distance approx 8.25 km from South Orleans

                                                                (1)  

                                                                  18

                                                                  Captain's Quarters @ Captain Alexander's Hideaway

                                                                  Harwich / West Harwich

                                                                  West Harwich house

                                                                  2 3 nights min

                                                                  • sleeps 2
                                                                  • 3 nights min
                                                                  • Beach / lakeside relaxation
                                                                  • Air conditioning
                                                                  • Private garden

                                                                  Price per night from

                                                                  $88

                                                                  Responds fast!
                                                                  avg. 2 hours 51 minutes

                                                                  Price per night from

                                                                  $88

                                                                  Distance approx 5.1 km from South Orleans Show on Map

                                                                  (2) Excellent 

                                                                    25

                                                                    Unique Style Chatham Villager In Heart Of It All

                                                                    Cape Cod / Chatham

                                                                    Chatham house

                                                                    3 8 min stay varies

                                                                    • 3 bedrooms
                                                                    • sleeps 8
                                                                    • min stay varies
                                                                    • Ask about children
                                                                    • Air conditioning

                                                                    Price per night from

                                                                    $331

                                                                    Price per night from

                                                                    $331

                                                                    Distance approx 7.09 km from South Orleans

                                                                    (9) Very Good 

                                                                      21

                                                                      Family Friendly, Near Golf, Beach & Center with A/C & Wifi

                                                                      Harwich / Harwich Port

                                                                      Harwich Port house

                                                                      3 6 2 nights min

                                                                      • 3 bedrooms
                                                                      • sleeps 6
                                                                      • 2 nights min
                                                                      • Ask about children
                                                                      • Air conditioning
                                                                      • Private garden

                                                                      Price per night from

                                                                      $280

                                                                      Price per night from

                                                                      $280

                                                                      Distance approx 1.76 km from South Orleans Show on Map

                                                                        20

                                                                        Summer on Cape Cod - only 2 weeks available in August

                                                                        Cape Cod / Orleans

                                                                        Orleans house

                                                                        4 6 3 nights min

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

                                                                        Price per night from

                                                                        $292

                                                                        Responds fast!
                                                                        avg. 1 hour 6 minutes

                                                                        Price per night from

                                                                        $292

                                                                        Distance approx 9.55 km from South Orleans

                                                                        (5) Very Good 

                                                                          23

                                                                          Stunning and peaceful, paradise found!

                                                                          Cape Cod / Wellfleet

                                                                          Wellfleet house

                                                                          3 8 7 nights min

                                                                          • 3 bedrooms
                                                                          • sleeps 8
                                                                          • 7 nights min
                                                                          • Beach / lakeside relaxation
                                                                          • Ask about children
                                                                          • Air conditioning

                                                                          Price per night from

                                                                          $408

                                                                          Price per night from

                                                                          $408

                                                                          Distance approx 9.89 km from South Orleans

                                                                          (4) Very Good 

                                                                            12

                                                                            33 FENWAY - WALK TO SEA STREET BEACH!

                                                                            Dennis / Dennis Port

                                                                            Dennis Port cottage

                                                                            3 6 min stay varies

                                                                            • 3 bedrooms
                                                                            • sleeps 6
                                                                            • min stay varies
                                                                            • Ask about children

                                                                            Price per night from

                                                                            $160

                                                                            Price per night from

                                                                            $160

                                                                            Distance approx 17.5 km from South Orleans

                                                                              13

                                                                              Beautiful Views and Short walk to beach

                                                                              Cape Cod / Hyannis

                                                                              Hyannis house

                                                                              4 8 7 nights min

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

                                                                              Price per night from

                                                                              $491

                                                                              Price per night from

                                                                              $491