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31 Houses

    33

    Exquisite Interior Designer’s House Short Walk to Lake Michigan

    Lake County / Highwood

    Highwood house

    4 6 min stay varies

    • 4 bedrooms
    • sleeps 6
    • min stay varies
    • Nearest beach 0.5 mi
    • Child Friendly
    • Air conditioning

    Price per night from

    $458

    Responds fast!
    avg. 1 hour 42 minutes

    Price per night from

    $458

    Great rentals within 20 miles that match your search

    Distance approx 17.21 km from Highwood

      9

      Barrington Village Townhome B

      Illinois / Barrington

      Barrington townhouse

      2 5 28 nights min

      • 2 bedrooms
      • sleeps 5
      • 28 nights min
      • Child Friendly

      Price per night from

      $180

      Price per night from

      $180

      Distance approx 18.86 km from Highwood

        12

        Comfy Quarters

        Illinois / River Grove

        River Grove house

        1 2 2 nights min

        • 1 bedroom
        • sleeps 2
        • 2 nights min
        • Car not necessary
        • Air conditioning
        • Private garden

        Price per night from

        $103

        Price per night from

        $103

        Distance approx 9.4 km from Highwood

          31

          2 Bdr Apt.★ King Bed ★ Near Great Lakes Naval Base

          Lake County / Libertyville

          Libertyville apartment

          2 8 2 nights min

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

          Price per night from

          $201

          Price per night from

          $201

          Distance approx 9.42 km from Highwood

            31

            2 Bedroom ★ King Bed ★ Near Great Lakes Naval Base

            Lake County / Libertyville

            Libertyville apartment

            2 10 2 nights min

            • 2 bedrooms
            • sleeps 10
            • 2 nights min
            • Child Friendly
            • Air conditioning

            Price per night from

            $201

            Price per night from

            $201

            Distance approx 13.64 km from Highwood

            (1) Excellent 

              15

              ⭐Perfect Getaway⭐Comfy King Bed✔Fast WiFi✔Smart TV✔Business Workspace✔Peaceful✔

              Illinois / Arlington Heights

              Arlington Heights apartment

              1 4 1 night min

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

              Price per night from

              $76

              Price per night from

              $76

              Distance approx 13.51 km from Highwood

              (1) Excellent 

                13

                Comfy King Bed, Cozy & Relaxing, Spacious 1BD, WiFi, Peaceful,Mins From Airport

                Illinois / Arlington Heights

                Arlington Heights apartment

                1 4 1 night min

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

                Price per night from

                $76

                Price per night from

                $76

                Distance approx 13.57 km from Highwood

                (1) Excellent 

                  13

                  ⭐Business Select⭐Mins FRM ✈Relaxing☕Free Parking✔Comfy King Bed✔Self Check-in✔

                  Illinois / Arlington Heights

                  Arlington Heights apartment

                  1 4 1 night min

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

                  Price per night from

                  $76

                  Price per night from

                  $76

                  Distance approx 18.89 km from Highwood

                  (1) Excellent 

                    18

                    Handsome 3BR in Lake View by Sonder

                    Illinois / Lincolnwood

                    Lincolnwood apartment

                    3 8 2 nights min

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

                    Price per night from

                    $95

                    Responds fast!
                    avg. 3 hours 44 minutes

                    Price per night from

                    $95

                    Distance approx 19.09 km from Highwood

                      21

                      Grand 3BR in Roscoe Village by Sonder

                      Illinois / Lincolnwood

                      Lincolnwood condo

                      3 7 min stay varies

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

                      Price per night from

                      $132

                      Responds fast!
                      avg. 3 hours 44 minutes

                      Price per night from

                      $132

                      Distance approx 11.79 km from Highwood

                        7

                        Pinewoods Retreat - Private Room

                        Illinois / Evanston

                        Evanston room

                        1 3 1 night min

                        • 1 bedroom
                        • sleeps 3
                        • 1 night min
                        • Child Friendly
                        • Air conditioning
                        • Pet Friendly

                        Price per night from

                        $59

                        Price per night from

                        $59

                        Distance approx 14.62 km from Highwood

                          19

                          Beach House Chicago

                          Illinois / Evanston

                          Evanston apartment

                          2 6 min stay varies

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

                          Price per night from

                          $124

                          Price per night from

                          $124

                          Distance approx 13.54 km from Highwood

                            15

                            Sleep Aboard Adeline’s Sea Moose: 68 ft Private Yacht Rentals Chicago Downtown

                            Illinois / Lincolnwood

                            Lincolnwood yacht

                            3 6 1 night min

                            • 3 bedrooms
                            • sleeps 6
                            • 1 night min
                            • Child Friendly
                            • Car not necessary
                            • Air conditioning

                            Price per night from

                            $1,374

                            Price per night from

                            $1,374

                            Distance approx 8.01 km from Highwood Show on Map

                            (3) Very Good 

                              27

                              Completely Remodeled 3-Bedroom House!

                              Illinois / Wheeling

                              Wheeling house

                              3 8 2 nights min

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

                              Price per night from

                              $138

                              Responds fast!
                              avg. 1 hour 55 minutes

                              Price per night from

                              $138

                              Distance approx 14.54 km from Highwood

                                8

                                Take A Pebble Apartments (Studio)

                                Lake County / Lake Zurich

                                Lake Zurich apartment

                                1 2 1 night min

                                • 1 bedroom
                                • sleeps 2
                                • 1 night min
                                • Air conditioning

                                Price per night from

                                $114

                                Price per night from

                                $114

                                Distance approx 1.73 km from Highwood Show on Map

                                  20

                                  Highland Park Luxury Home- 2000 square foot Suite

                                  Lake County / Highland Park

                                  Highland Park b and b

                                  2 8 2 nights min

                                  • 2 bedrooms
                                  • sleeps 8
                                  • 2 nights min
                                  • Beach / lakeside relaxation
                                  • Car not necessary
                                  • Air conditioning

                                  Price per night from

                                  $115

                                  Price per night from

                                  $115

                                  Distance approx 13.55 km from Highwood

                                  (1) Excellent 

                                    15

                                    ⭐King Bed⭐Business Workspace✔Fast WiFi✔Mins From ✈Smart TVs✔Cozy & Relaxing✔

                                    Illinois / Arlington Heights

                                    Arlington Heights apartment

                                    1 4 1 night min

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

                                    Price per night from

                                    $76

                                    Price per night from

                                    $76

                                    Distance approx 8.92 km from Highwood

                                    (2) Excellent 

                                      30

                                      Beautifully Remodeled 3 BR Townhouse near Chicago

                                      Illinois / Wilmette

                                      Wilmette townhouse

                                      3 10 2 nights min

                                      • 3 bedrooms
                                      • sleeps 10
                                      • 2 nights min
                                      • Child Friendly
                                      • Air conditioning
                                      • Private garden

                                      Price per night from

                                      $149

                                      Responds fast!
                                      avg. 1 hour 55 minutes

                                      Price per night from

                                      $149

                                      Distance approx 9.26 km from Highwood

                                        35

                                        2 Bdr House - Perfect for Navy Graduations!!!

                                        Lake County / Libertyville

                                        Libertyville house

                                        2 6 2 nights min

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

                                        Price per night from

                                        $207

                                        Price per night from

                                        $207

                                        Distance approx 9.64 km from Highwood

                                          20

                                          4 Bedroom House Close to Great Lakes Naval Station

                                          Lake County / Libertyville

                                          Libertyville house

                                          4 8 2 nights min

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

                                          Price per night from

                                          $229

                                          Price per night from

                                          $229

                                          Distance approx 9.39 km from Highwood

                                            28

                                            3 Bedrooms w/ King Beds ★ Near Great Lakes Naval

                                            Lake County / Libertyville

                                            Libertyville apartment

                                            3 10 2 nights min

                                            • 3 bedrooms
                                            • sleeps 10
                                            • 2 nights min
                                            • Child Friendly
                                            • Air conditioning

                                            Price per night from

                                            $229

                                            Price per night from

                                            $229

                                            Distance approx 15.91 km from Highwood

                                              24

                                              Luxe Chicago Townhome w/ Balcony - 20 Mins to DT!

                                              Illinois / Lincolnwood

                                              Lincolnwood house

                                              2 4 min stay varies

                                              • 2 bedrooms
                                              • sleeps 4
                                              • min stay varies
                                              • Air conditioning

                                              Price per night from

                                              $144

                                              Responds fast!
                                              avg. 19 minutes

                                              Price per night from

                                              $144

                                              Distance approx 13.73 km from Highwood

                                                22

                                                Hull Chateau

                                                Illinois / Evanston

                                                Evanston house

                                                2 7 1 night min

                                                • 2 bedrooms
                                                • sleeps 7
                                                • 1 night min
                                                • Nearest beach 2 mi
                                                • Child Friendly
                                                • Car not necessary

                                                Price per night from

                                                $255

                                                Price per night from

                                                $255

                                                Distance approx 13.63 km from Highwood

                                                (1) Excellent 

                                                  13

                                                  ⭐Comfy✔King Bed✔WiFi✔4K Cable TV✔Business✔Family⭐On-Site Parking⭐Self Check-in⭐

                                                  Illinois / Arlington Heights

                                                  Arlington Heights apartment

                                                  1 4 1 night min

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

                                                  Price per night from

                                                  $111

                                                  Price per night from

                                                  $111

                                                  Distance approx 9.43 km from Highwood

                                                    34

                                                    3 Bedrooms w/ King Beds ★ Near Great Lakes Naval

                                                    Lake County / Libertyville

                                                    Libertyville apartment

                                                    3 8 2 nights min

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

                                                    Price per night from

                                                    $229

                                                    Price per night from

                                                    $229

                                                    Distance approx 13.51 km from Highwood

                                                    (1) Excellent 

                                                      15

                                                      ⭐Home Away From Home⭐Perfect For Business Stays❤Peaceful ❤Relaxing❤Comfy Beds

                                                      Illinois / Arlington Heights

                                                      Arlington Heights apartment

                                                      1 4 1 night min

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

                                                      Price per night from

                                                      $76

                                                      Price per night from

                                                      $76

                                                      Distance approx 19.18 km from Highwood

                                                        13

                                                        Two Bedroom Unit in Prime Logan Square Location

                                                        Illinois / Oak Park

                                                        Oak Park apartment

                                                        2 7 min stay varies

                                                        • 2 bedrooms
                                                        • sleeps 7
                                                        • min stay varies
                                                        • Child Friendly
                                                        • Air conditioning

                                                        Price per night from

                                                        $115

                                                        Responds fast!
                                                        avg. 3 hours 31 minutes

                                                        Price per night from

                                                        $115

                                                        Distance approx 18.77 km from Highwood

                                                          12

                                                          Modern 3 bedroom in Heart of Wrigleyville

                                                          Illinois / Lincolnwood

                                                          Lincolnwood apartment

                                                          3 8 min stay varies

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

                                                          Price per night from

                                                          $165

                                                          Responds fast!
                                                          avg. 3 hours 31 minutes

                                                          Price per night from

                                                          $165

                                                          Distance approx 18.96 km from Highwood

                                                            24

                                                            Garden-Level Apartment w/ Yard & On-Site Parking, 4-minute Walk to Metro!

                                                            Illinois / Lincolnwood

                                                            Lincolnwood apartment

                                                            2 4 min stay varies

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

                                                            Price per night from

                                                            $129

                                                            Price per night from

                                                            $129

                                                            Distance approx 18.94 km from Highwood

                                                              25

                                                              Spacious Luxurious Private Apartment Sleeps 5

                                                              Illinois / Elmwood Park

                                                              Elmwood Park apartment

                                                              2 5 1 night min

                                                              • 2 bedrooms
                                                              • sleeps 5
                                                              • 1 night min
                                                              • Child Friendly
                                                              • Air conditioning
                                                              • Private garden

                                                              Price per night from

                                                              $79

                                                              Responds fast!
                                                              avg. 54 minutes

                                                              Price per night from

                                                              $79

                                                              Distance approx 18.89 km from Highwood

                                                                23

                                                                Vintage 3BR in Lake View by Sonder

                                                                Illinois / Lincolnwood

                                                                Lincolnwood apartment

                                                                3 8 2 nights min

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

                                                                Price per night from

                                                                $119

                                                                Responds fast!
                                                                avg. 3 hours 44 minutes

                                                                Price per night from

                                                                $119