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93 Houses

(1) Excellent 

    16

    5 Bdrm 3 Bth Lake Michigan Waterfront Private Pool

    Indiana / Chesterton

    Chesterton house

    5 20 min stay varies

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

    Price per night from

    $1,135

    Price per night from

    $1,135

    Great rentals within 20 miles that match your search

    Distance approx 12.29 km from Chesterton

    (23) Excellent 

      39

      Sun King--Brand New 6th Full Bathroom!--Huge Beautiful Home

      Indiana / Michigan City

      Michigan City house

      7 24 min stay varies

      • 7 bedrooms
      • sleeps 24
      • min stay varies
      • Beach / lakeside relaxation
      • Nearest beach 0.32 mi
      • Swimming pool
      “What an awesome space to be together with family!” There was plenty of room and space for everyone and everything! -- A wrap around porch, two LARGE dining areas, plenty of counter space in the kitchen with a large island as well (with stools for more
      …see more

      Price per night from

      $450

      Responds fast!
      avg. 46 minutes

      Price per night from

      $450

      Distance approx 12.34 km from Chesterton

      (19) Excellent 

        36

        Moondance--Huge Open Concept in Central Beachwalk

        Indiana / Michigan City

        Michigan City house

        6 16 min stay varies

        • 6 bedrooms
        • sleeps 16
        • min stay varies
        • Beach / lakeside relaxation
        • Nearest beach 0.02 mi
        • Swimming pool
        “Great location with great amenities” Loved the house. Great floor plan for large families and extended family. Loved the boardwalk to the beach and the trail around the lake. The kids liked the basketball court and the play area. The office was he
        …see more

        Price per night from

        $349

        Responds fast!
        avg. 46 minutes

        Price per night from

        $349

        Distance approx 12.35 km from Chesterton

        (5) Very Good 

          9

          Mint Julep

          Indiana / Michigan City

          Michigan City house

          2 6 min stay varies

          • 2 bedrooms
          • sleeps 6
          • min stay varies
          • Beach / lakeside relaxation
          • Swimming pool
          • Child Friendly

          Price per night from

          $176

          Price per night from

          $176

          Distance approx 10.73 km from Chesterton

          (22) Very Good 

          Certificate of Excellence

            16

            Lighthouse Apartment Rental

            Indiana / Michigan City

            Michigan City apartment

            2 4 3 nights min

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

            Certificate of Excellence

            Price per night from

            $172

            Responds fast!
            avg. 3 hours 24 minutes

            Price per night from

            $172

            Distance approx 16 km from Chesterton

            (9) Excellent 

              16

              4 bed Waterfront Getaway Laporte Pine Lake pier

              Indiana / LaPorte

              LaPorte house

              4 12 min stay varies

              • 4 bedrooms
              • sleeps 12
              • min stay varies
              • Beach / lakeside relaxation
              • Child Friendly
              • Air conditioning
              “Excellent Accommodations!” It is not easy to find a place that will comfortably fit our large family. However, this place did just that! It was super spacious and clean. We had easy access to the water, which was great since we had two boats. The
              …see more

              Price per night from

              $257

              Responds fast!
              avg. 18 minutes

              Price per night from

              $257

              Distance approx 12.1 km from Chesterton

              (4) Excellent 

                28

                4BR 3BA Short Walk to Beach - New Furnishings 8/15

                Indiana / Michigan City

                Michigan City house

                4 14 2 nights min

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

                Price per night from

                $628

                Price per night from

                $628

                Distance approx 12.35 km from Chesterton

                (7) Very Good 

                  19

                  Southern Belle

                  Indiana / Michigan City

                  Michigan City house

                  5 14 min stay varies

                  • 5 bedrooms
                  • sleeps 14
                  • min stay varies
                  • Beach / lakeside relaxation
                  • Nearest beach 0 mi
                  • Swimming pool

                  Price per night from

                  $628

                  Price per night from

                  $628

                  Distance approx 12.74 km from Chesterton

                  (3) Excellent 

                    24

                    View of the lake from 2 decks - Lakeshore Dr 6br!

                    Indiana / Michigan City

                    Michigan City house

                    6 15 2 nights min

                    • 6 bedrooms
                    • sleeps 15
                    • 2 nights min
                    • Beach / lakeside relaxation
                    • Child Friendly
                    • Air conditioning

                    Price per night from

                    $915

                    Price per night from

                    $915

                    Distance approx 17.06 km from Chesterton

                    (15) Excellent 

                      23

                      Beautifully Renovated 'Pinebrook Cottage' 2BR 1BA

                      Berrien County / New Buffalo

                      New Buffalo house

                      2 6 2 nights min

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

                      Price per night from

                      $298

                      Responds fast!
                      avg. 40 minutes

                      Price per night from

                      $298

                      Distance approx 10.54 km from Chesterton

                      (1) Very Good 

                        18

                        Il Giardino

                        Indiana / Michigan City

                        Michigan City house

                        3 8 3 nights min

                        • 3 bedrooms
                        • sleeps 8
                        • 3 nights min
                        • Nearest beach 5 mi
                        • Child Friendly
                        • Air conditioning

                        Price per night from

                        $269

                        Price per night from

                        $269

                        Distance approx 17.51 km from Chesterton

                        (3) Excellent 

                          33

                          TreeTops at Grand Beach. 5* rated. Block to Lake MI. Golf Cart (in season)

                          Berrien County / New Buffalo

                          New Buffalo house

                          3 9 min stay varies

                          • 3 bedrooms
                          • sleeps 9
                          • min stay varies
                          • Beach / lakeside relaxation
                          • Child Friendly
                          • Air conditioning

                          Price per night from

                          $229

                          Responds fast!
                          avg. 38 minutes

                          Price per night from

                          $229

                          Distance approx 11.99 km from Chesterton

                          (11) Very Good 

                            41

                            On the beach with rooftop Great VIEWS!! Lake Michigan in your Back yard

                            Indiana / Michigan City

                            Michigan City townhouse

                            3 16 min stay varies

                            • 3 bedrooms
                            • sleeps 16
                            • min stay varies
                            • Child Friendly
                            • Air conditioning
                            • Private garden

                            Price per night from

                            $371

                            Price per night from

                            $371

                            Distance approx 12.3 km from Chesterton

                            (2) Excellent 

                              41

                              Poseidon--Beachwalk's Largest Home. The King of Beachwalk.

                              Indiana / Michigan City

                              Michigan City house

                              8 27 min stay varies

                              • 8 bedrooms
                              • sleeps 27
                              • min stay varies
                              • Swimming pool
                              • Child Friendly
                              • Air conditioning

                              Price per night from

                              $449

                              Responds fast!
                              avg. 46 minutes

                              Price per night from

                              $449

                              Distance approx 12.37 km from Chesterton

                              (2) Very Good 

                                22

                                My Blue Heaven

                                Indiana / Michigan City

                                Michigan City house

                                6 16 min stay varies

                                • 6 bedrooms
                                • sleeps 16
                                • min stay varies
                                • Swimming pool
                                • Child Friendly
                                • Air conditioning

                                Price per night from

                                $687

                                Price per night from

                                $687

                                Distance approx 16.37 km from Chesterton

                                (2) Excellent 

                                  24

                                  Lake front house 4 bedroom Pier to dock your boat! Gorgeous view!

                                  Indiana / LaPorte

                                  LaPorte house

                                  4 12 min stay varies

                                  • 4 bedrooms
                                  • sleeps 12
                                  • min stay varies
                                  • Nearest beach 3 mi
                                  • Child Friendly
                                  • Air conditioning

                                  Price per night from

                                  $229

                                  Price per night from

                                  $229

                                  Distance approx 10.73 km from Chesterton

                                  (22) Excellent 

                                  Certificate of Excellence

                                    16

                                    Lighthouse apt. Great location right by Lighthouse Outlet Mall See the Sale!

                                    Indiana / Michigan City

                                    Michigan City apartment

                                    1 3 3 nights min

                                    • 1 bedroom
                                    • sleeps 3
                                    • 3 nights min
                                    • Beach / lakeside relaxation
                                    • Nearest beach 2 mi
                                    • Child Friendly
                                    “Great stay!!” This apartment was perfect for our vacation. The location is great (right by the outlets and many restaurants)! The kids loved it and Darlene was a wonderful host (thanks for the cookies!!) I would highly recommend this rental to anyo
                                    …see more

                                    Certificate of Excellence

                                    Price per night from

                                    $147

                                    Responds fast!
                                    avg. 3 hours 24 minutes

                                    Price per night from

                                    $147

                                    Distance approx 17.76 km from Chesterton

                                    (3) Excellent 

                                      24

                                      Everything Is New From Beds To Kitchen Cabinets

                                      Berrien County / New Buffalo

                                      New Buffalo cottage

                                      2 6 2 nights min

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

                                      Price per night from

                                      $257

                                      Responds fast!
                                      avg. 3 hours 10 minutes

                                      Price per night from

                                      $257

                                      Distance approx 15.17 km from Chesterton

                                      (1) Excellent 

                                        29

                                        Charming Lake Michigan Bungalow, sleeps 12

                                        Indiana / Michigan City

                                        Michigan City house

                                        3 12 min stay varies

                                        • 3 bedrooms
                                        • sleeps 12
                                        • min stay varies
                                        • Beach / lakeside relaxation
                                        • Child Friendly
                                        • Air conditioning

                                        Price per night from

                                        $229

                                        Responds fast!
                                        avg. 1 hour 32 minutes

                                        Price per night from

                                        $229

                                        Distance approx 10.74 km from Chesterton

                                        (13) Excellent 

                                          13

                                          Beautiful apt. across from Lighthouse Mall

                                          Indiana / Michigan City

                                          Michigan City apartment

                                          1 2 3 nights min

                                          • 1 bedroom
                                          • sleeps 2
                                          • 3 nights min
                                          • Beach / lakeside relaxation
                                          • Nearest beach 2 mi
                                          • Air conditioning
                                          “I love it!” Had an amazing weekend away it was perfect! Busy everyday doing something fun, got to enjoy the beach, the mall, had really good tasting food and everyone was super nice around town!
                                          …see more

                                          Price per night from

                                          $143

                                          Responds fast!
                                          avg. 3 hours 24 minutes

                                          Price per night from

                                          $143

                                          Distance approx 16.25 km from Chesterton

                                          (1) Excellent 

                                            29

                                            Michiana Shores Cottage 2BR 2BA - Walk to Beach!

                                            Indiana / Michiana Shores

                                            Michiana Shores house

                                            2 7 2 nights min

                                            • 2 bedrooms
                                            • sleeps 7
                                            • 2 nights min
                                            • Beach / lakeside relaxation
                                            • Nearest beach 0.3 mi
                                            • Child Friendly

                                            Price per night from

                                            $410

                                            Price per night from

                                            $410

                                            Distance approx 10.73 km from Chesterton

                                            (25) Excellent 

                                            Certificate of Excellence

                                              16

                                              Beautiful apt next to Lighthouse Outlet Mall

                                              Indiana / Michigan City

                                              Michigan City apartment

                                              1 3 min stay varies

                                              • 1 bedroom
                                              • sleeps 3
                                              • min stay varies
                                              • Beach / lakeside relaxation
                                              • Nearest beach 2 mi
                                              • Ask about children
                                              “Beautiful Apartment and Darlene was Awesome.” My husband and I arrived at the apartments for a 2 night stay and was greeted by the owner Darlene. She later came back to our unit with cans of pop, water and she even make us home made chocolate cookies!
                                              …see more

                                              Certificate of Excellence

                                              Price per night from

                                              $143

                                              Responds fast!
                                              avg. 3 hours 24 minutes

                                              Price per night from

                                              $143

                                              Distance approx 16.73 km from Chesterton

                                                19

                                                Conveniently Located Hidden Gem in Griffith/Gary Completely Renovated

                                                Indiana / Griffith

                                                Griffith house

                                                3 7 2 nights min

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

                                                Price per night from

                                                $140

                                                Price per night from

                                                $140

                                                Distance approx 12.38 km from Chesterton

                                                  20

                                                  Pistachio's Paradise 1.5 min walk to the beach!

                                                  Indiana / Michigan City

                                                  Michigan City house

                                                  3 12 min stay varies

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

                                                  Price per night from

                                                  $586

                                                  Price per night from

                                                  $586

                                                  Distance approx 15.34 km from Chesterton

                                                  (1) Excellent 

                                                    26

                                                    Colorado Place

                                                    Indiana / Merrillville

                                                    Merrillville house

                                                    3 10 2 nights min

                                                    • 3 bedrooms
                                                    • sleeps 10
                                                    • 2 nights min
                                                    • Nearest beach 12 mi
                                                    • Child Friendly
                                                    • Pet Friendly

                                                    Price per night from

                                                    $113

                                                    Price per night from

                                                    $113

                                                    Distance approx 6.33 km from Chesterton Show on Map

                                                      19

                                                      Cozy Cottage

                                                      Indiana / Portage

                                                      Portage house

                                                      3 7 2 nights min

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

                                                      Price per night from

                                                      $160

                                                      Price per night from

                                                      $160

                                                      Distance approx 13.86 km from Chesterton

                                                        6

                                                        Dune Farmhouse

                                                        Indiana / Long Beach

                                                        Long Beach house

                                                        2 4 2 nights min

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

                                                        Price per night from

                                                        $293

                                                        Price per night from

                                                        $293

                                                        Distance approx 10.07 km from Chesterton

                                                        (1) Excellent 

                                                          35

                                                          Indiana Dunes Beach Getaway Home

                                                          Indiana / Lake Station

                                                          Lake Station house

                                                          4 12 2 nights min

                                                          • 4 bedrooms
                                                          • sleeps 12
                                                          • 2 nights min
                                                          • Nearest beach 1 mi
                                                          • Child Friendly
                                                          • Air conditioning

                                                          Price per night from

                                                          $284

                                                          Price per night from

                                                          $284

                                                          Distance approx 11.91 km from Chesterton

                                                            7

                                                            CONDO FOR RENT IN FLORIDA

                                                            Broward County / Fort Lauderdale

                                                            Fort Lauderdale condo

                                                            1 4 90 nights min

                                                            • 1 bedroom
                                                            • sleeps 4
                                                            • 90 nights min
                                                            • Swimming pool
                                                            • Child Friendly

                                                            Price per night from

                                                            $67

                                                            Price per night from

                                                            $67

                                                            Distance approx 11.92 km from Chesterton

                                                              24

                                                              Dune our Thing- 1 block to beach with private parking and lake views!

                                                              Indiana / Michigan City

                                                              Michigan City house

                                                              6 16 min stay varies

                                                              • 6 bedrooms
                                                              • sleeps 16
                                                              • min stay varies
                                                              • Nearest beach 0.08 mi
                                                              • Child Friendly
                                                              • Air conditioning

                                                              Price per night from

                                                              $456

                                                              Price per night from

                                                              $456

                                                              Distance approx 7.06 km from Chesterton

                                                                21

                                                                Lakefront Lakehouse. Relax, fish, sunbathe and swim in your private backyard

                                                                Indiana / Valparaiso

                                                                Valparaiso house

                                                                2 6 min stay varies

                                                                • 2 bedrooms
                                                                • sleeps 6
                                                                • min stay varies
                                                                • Child Friendly
                                                                • Air conditioning
                                                                • Private garden

                                                                Price per night from

                                                                $135

                                                                Price per night from

                                                                $135

                                                                Distance approx 16.55 km from Chesterton

                                                                  6

                                                                  5-Bedroom Single Family Home

                                                                  Illinois / Bellwood

                                                                  Bellwood house

                                                                  5 8 3 nights min

                                                                  • 5 bedrooms
                                                                  • sleeps 8
                                                                  • 3 nights min
                                                                  • Child Friendly

                                                                  Price per night from

                                                                  $229

                                                                  Price per night from

                                                                  $229

                                                                  Distance approx 10.29 km from Chesterton

                                                                    33

                                                                    Avant Garde Home with Private Indoor Heated Pool and Sauna

                                                                    Indiana / Valparaiso

                                                                    Valparaiso house

                                                                    4 15 2 nights min

                                                                    • 4 bedrooms
                                                                    • sleeps 15
                                                                    • 2 nights min
                                                                    • Nearest beach 26 mi
                                                                    • Swimming pool
                                                                    • Child Friendly

                                                                    Price per night from

                                                                    $293

                                                                    Price per night from

                                                                    $293

                                                                    Distance approx 12.29 km from Chesterton

                                                                      23

                                                                      BeachHouse/Hot Tub(all year)Hot Rock Sauna/Jacuzzi/Pets OK

                                                                      Indiana / Michigan City

                                                                      Michigan City apartment

                                                                      3 4 1 night min

                                                                      • 3 bedrooms
                                                                      • sleeps 4
                                                                      • 1 night min
                                                                      • Child Friendly
                                                                      • Air conditioning

                                                                      Price per night from

                                                                      $279

                                                                      Price per night from

                                                                      $279

                                                                      Distance approx 14.94 km from Chesterton

                                                                      (1) Excellent 

                                                                        15

                                                                        Beach Home in Long Beach, Indiana

                                                                        Indiana / Long Beach

                                                                        Long Beach house

                                                                        3 12 7 nights min

                                                                        • 3 bedrooms
                                                                        • sleeps 12
                                                                        • 7 nights min
                                                                        • Child Friendly
                                                                        • Air conditioning
                                                                        • Private garden

                                                                        Price per night from

                                                                        $458

                                                                        Price per night from

                                                                        $458

                                                                        Distance approx 12.29 km from Chesterton

                                                                          25

                                                                          Beachfront/Hot Tub(all year)Steam Room/Jacuzzi/Pets/2Night Min/Beach Wheelchair

                                                                          Indiana / Michigan City

                                                                          Michigan City apartment

                                                                          1 4 1 night min

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

                                                                          Price per night from

                                                                          $297

                                                                          Price per night from

                                                                          $297

                                                                          Distance approx 3.74 km from Chesterton Show on Map

                                                                            10

                                                                            DunesWalk Inn - Vacation Rental

                                                                            Indiana / Beverly Shores

                                                                            Beverly Shores hotel apartment

                                                                            5 19 2 nights min

                                                                            • 5 bedrooms
                                                                            • sleeps 19
                                                                            • 2 nights min
                                                                            • Child Friendly
                                                                            • Air conditioning
                                                                            • Private garden

                                                                            Price per night from

                                                                            $850

                                                                            Price per night from

                                                                            $850

                                                                            Distance approx 16.73 km from Chesterton

                                                                              29

                                                                              4 bed 2 bath Chicagoland Home

                                                                              Indiana / Merrillville

                                                                              Merrillville house

                                                                              4 8 2 nights min

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

                                                                              Price per night from

                                                                              $159

                                                                              Price per night from

                                                                              $159