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22 Houses

(1) Excellent 

    17

    Lake Michigan by Whistling Straits

    Wisconsin / Sheboygan

    Sheboygan house

    2 6 2 nights min

    • 2 bedrooms
    • sleeps 6
    • 2 nights min
    • Beach / lakeside relaxation
    • Nearest beach 1 mi
    • Child Friendly

    Price per night from

    $567

    Responds fast!
    avg. 1 hour 6 minutes

    Price per night from

    $567

    (15) Excellent 

      7

      Lake Shore House on Lake Michigan! Dog Friendly!

      Wisconsin / Sheboygan

      Sheboygan house

      2 7 min stay varies

      • 2 bedrooms
      • sleeps 7
      • min stay varies
      • Beach / lakeside relaxation
      • Nearest beach 1 mi
      • Child Friendly
      “The Lakeshore House is just as nice as the pictures make it look!” My husband and I loved the Lakeshore House. It was cute, clean, and had beautiful views. There were many thoughtful surprises, like binoculars to view the birds and boats on the lake,
      …see more

      Price per night from

      $108

      Responds fast!
      avg. 1 hour 19 minutes

      Price per night from

      $108

      (2) Very Good 

        18

        REMODELED HOUSE ON LAKE MICHIGAN

        Wisconsin / Sheboygan

        Sheboygan house

        3 8 2 nights min

        • 3 bedrooms
        • sleeps 8
        • 2 nights min
        • Beach / lakeside relaxation
        • Nearest beach 0.64 mi
        • Child Friendly

        Price per night from

        $172

        Responds fast!
        avg. 1 hour 41 minutes

        Price per night from

        $172

        (1) Excellent 

          19

          Historic Mansion Right on Lake Michigan!

          Wisconsin / Sheboygan

          Sheboygan villa

          9 25 3 nights min

          • 9 bedrooms
          • sleeps 25
          • 3 nights min
          • Beach / lakeside relaxation
          • Child Friendly
          • Car not necessary

          Price per night from

          $1,707

          Price per night from

          $1,707

            18

            Bright and Beautiful Lake Escape

            Wisconsin / Sheboygan

            Sheboygan house

            2 9 2 nights min

            • 2 bedrooms
            • sleeps 9
            • 2 nights min
            • Beach / lakeside relaxation
            • Child Friendly

            Price per night from

            $241

            Price per night from

            $241

              19

              REMODELED HOME OVERLOOKING LAKE MICHIGAN

              Wisconsin / Sheboygan

              Sheboygan house

              3 8 1 night min

              • 3 bedrooms
              • sleeps 8
              • 1 night min
              • Child Friendly
              • Air conditioning

              Price per night from

              $384

              Price per night from

              $384

              (1) Very Good 

                12

                BEACHSIDE GETAWAY

                Wisconsin / Sheboygan

                Sheboygan condo

                2 4 2 nights min

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

                Price per night from

                $144

                Price per night from

                $144

                  6

                  Centrally Located Sheboygan Charmer: Near Blue Harbor, Kohler & Lake MIchigan

                  Wisconsin / Sheboygan

                  Sheboygan house

                  4 7 2 nights min

                  • 4 bedrooms
                  • sleeps 7
                  • 2 nights min
                  • Air conditioning
                  • Private garden

                  Price per night from

                  $172

                  Price per night from

                  $172

                    24

                    NEW! Updated Sheboygan Home w/Porch

                    Wisconsin / Sheboygan

                    Sheboygan house

                    3 7 min stay varies

                    • 3 bedrooms
                    • sleeps 7
                    • min stay varies
                    • Child Friendly

                    Price per night from

                    $184

                    Responds fast!
                    avg. 8 minutes

                    Price per night from

                    $184

                    Great rentals within 20 miles that match your search

                    Distance approx 16.26 km from Sheboygan

                      26

                      Elkhart LakeTownhome w/Backyard- 1 Block to Beach!

                      Wisconsin / Elkhart Lake

                      Elkhart Lake house

                      3 8 min stay varies

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

                      Price per night from

                      $228

                      Responds fast!
                      avg. 58 minutes

                      Price per night from

                      $228

                      Distance approx 16.26 km from Sheboygan

                        28

                        3BR Elkhart Lake Townhome w/Multiple Porches

                        Wisconsin / Elkhart Lake

                        Elkhart Lake house

                        3 8 2 nights min

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

                        Price per night from

                        $487

                        Responds fast!
                        avg. 8 minutes

                        Price per night from

                        $487

                        Distance approx 15.97 km from Sheboygan

                        (12) Excellent 

                          32

                          Aspen House - Private, peaceful country home near Elkhart Lake

                          Wisconsin / Elkhart Lake

                          Elkhart Lake house

                          3 5 3 nights min

                          • 3 bedrooms
                          • sleeps 5
                          • 3 nights min
                          • Nearest beach 4 mi
                          • Child Friendly
                          • Air conditioning
                          “The best vacation rental ever!” I would like to start by thanking Nanette & Hans for their hospitality and personal caring to make my experience even more worthwhile. 95 private acres ... wow, you will feel like you own it! :) I felt completely comfo
                          …see more

                          Price per night from

                          $252

                          Responds fast!
                          avg. 17 minutes

                          Price per night from

                          $252

                          Distance approx 15.75 km from Sheboygan

                            24

                            NEW! Bright 4BR Plymouth Cottage on Crystal Lake

                            Wisconsin / Plymouth

                            Plymouth cottage

                            4 14 min stay varies

                            • 4 bedrooms
                            • sleeps 14
                            • min stay varies
                            • Child Friendly
                            • Air conditioning
                            • Pet Friendly

                            Price per night from

                            $189

                            Responds fast!
                            avg. 8 minutes

                            Price per night from

                            $189

                            Distance approx 10.06 km from Sheboygan

                              24

                              Charming Oostburg Home w/ Kayaks on Lake Michigan!

                              Wisconsin / Oostburg

                              Oostburg log cabin

                              2 5 min stay varies

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

                              Price per night from

                              $207

                              Responds fast!
                              avg. 21 minutes

                              Price per night from

                              $207

                              Distance approx 8.95 km from Sheboygan

                                19

                                Aunt Dot's Cottage on the Shores of Lake Michigan

                                Wisconsin / Oostburg

                                Oostburg house

                                3 6 3 nights min

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

                                Price per night from

                                $380

                                Price per night from

                                $380

                                Distance approx 17.1 km from Sheboygan

                                  10

                                  Beautiful Victorian Near Racing, Golfing, & Hiking

                                  Wisconsin / Glenbeulah

                                  Glenbeulah house

                                  4 7 2 nights min

                                  • 4 bedrooms
                                  • sleeps 7
                                  • 2 nights min

                                  Price per night from

                                  $516

                                  Price per night from

                                  $516

                                  Distance approx 19.36 km from Sheboygan

                                    34

                                    Valders Log Cabin near EEA Air Show & Sheboygan!

                                    Wisconsin / Valders

                                    Valders log cabin

                                    2 6 min stay varies

                                    • 2 bedrooms
                                    • sleeps 6
                                    • min stay varies
                                    • Child Friendly

                                    Price per night from

                                    $228

                                    Responds fast!
                                    avg. 8 minutes

                                    Price per night from

                                    $228

                                    Distance approx 15.18 km from Sheboygan

                                    (2) Excellent 

                                      12

                                      *Luxury Villa. Brilliant Location. Guest Approved.*

                                      Wisconsin / Elkhart Lake

                                      Elkhart Lake villa

                                      3 8 min stay varies

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

                                      Price per night from

                                      $916

                                      Price per night from

                                      $916

                                      Distance approx 15.2 km from Sheboygan

                                        8

                                        *Entertainment Villa. Close to Everything.*

                                        Wisconsin / Elkhart Lake

                                        Elkhart Lake villa

                                        4 12 min stay varies

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

                                        Price per night from

                                        $573

                                        Price per night from

                                        $573

                                        Distance approx 11.41 km from Sheboygan Show on Map

                                        (1) Very Good 

                                          17

                                          RESToration House

                                          Wisconsin / Cleveland

                                          Cleveland house

                                          1 6 3 nights min

                                          • 1 bedroom
                                          • sleeps 6
                                          • 3 nights min
                                          • Beach / lakeside relaxation
                                          • Child Friendly
                                          • Air conditioning

                                          Price per night from

                                          $172

                                          Responds fast!
                                          avg. 3 hours 30 minutes

                                          Price per night from

                                          $172

                                          Distance approx 10.51 km from Sheboygan

                                            21

                                            Great Place on a Great Lake 15 minutes from "Destination Kohler"

                                            Wisconsin / Oostburg

                                            Oostburg house

                                            3 6 2 nights min

                                            • 3 bedrooms
                                            • sleeps 6
                                            • 2 nights min
                                            • Nearest beach 0 mi
                                            • Child Friendly
                                            • Air conditioning

                                            Price per night from

                                            $287

                                            Price per night from

                                            $287

                                            Distance approx 6.05 km from Sheboygan Show on Map

                                              29

                                              River Meadow Getaway in Sheboygan Falls

                                              Wisconsin / Sheboygan Falls

                                              Sheboygan Falls house

                                              4 6 min stay varies

                                              • 4 bedrooms
                                              • sleeps 6
                                              • min stay varies
                                              • Nearest beach 12 mi
                                              • Child Friendly
                                              • Air conditioning

                                              Price per night from

                                              $293

                                              Price per night from

                                              $293