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Highland Park Vacation Rentals

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    Don't let other travelers get your favorite Highland Park area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 16 Rentals in Highland Park
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    Highland Park
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    The following rentals are within 15 miles of Highland Park.
    Beautifully Remodeled 3 BR Townhouse near Chicago1 / 30
    (2)Excellent
    Wilmette, IL
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Completely Remodeled 3-Bedroom House!1 / 27
    (3)Very good
    Wheeling, IL
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Lincolnwood, IL
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Washer
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    At this Sonder, you'll love the beautiful fireplace, spacious balcony, and a fully-equipped kitchen. Located in Lakeview, know for its delicious dining and relaxed cafes. Every booking is instantly confirmed. Every call or message is answered within minutes. Every home is equipped with crisp...
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    Lincolnwood, Illinois 60613
    Condo/Apartment - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Handsome 3BR in Lake View by Sonder1 / 18
    (1)Excellent
    Lincolnwood, IL
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 11, 2018
    Great space in a great location. Within walking distance to a number of restaurants/bars. The apartment was clean and looked just like the photos. Reservations were extremely...
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    About this property
    At this Sonder, you'll love the stunning architectural details, luxurious hardwood floors, and a spacious balcony. Located in Lakeview, known for its amazing eateries and relaxed cafes. Every booking is instantly confirmed. Every call or message is answered within minutes. Every home is equipped...
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    Lincolnwood, Illinois 60613
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Lincolnwood, IL
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    At this Sonder, you'll love the expansive living area, sleek hardwood floors, and fully-equipped kitchen. Located in Roscoe Village, known for its hip boutiques and assortment of delicious restaurants. When you stay at a Sonder, you have a 24/7 concierge and receive all the local color of a...
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    Location Information
    Lincolnwood, Illinois 60618
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Just north of Chicago1 / 8
    (19)Excellent
    Winnetka, IL
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Wi-Fi
    • Private Yard
    • Air Conditioning
    • Secure Parking
    • Patio
    • DVD Player
    • Shared Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 17, 2017
    Loved this place. It was perfect for a family vacation for my husband, myself and our two early 20 year old sons. Cottage was very well equipped, convenient to the Metra to...
    Reviewed November 23, 2016
    Cottage is cozy, convenient to trains, and in a charming residential neighborhood. Wonderful owners too.
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    About this property
    Our 2 Bedroom Cottage has a private brick patio, full kitchen, full bath, window Ac and wifi. We are walking distance to train, buses, village of Winnetka, beaches and parks. This is a lovely, quiet, tree lined suburb 19 miles (31km) north of downtown Chicago. Trains/buses make access to Chicago...
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    Winnetka, Illinois 60093
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Lincolnwood, IL
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Waterfront
    • Wi-Fi
    • Balcony
    • Patio
    • Terrace
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Adeline's Sea Moose hosts over night stays for yacht enthusiasts! This 68 ft luxury charter yacht is one of the few sizable multi-level private Charter yachts in Chicago, and that was built and has maintained a true private yacht. Great care has been taken to uphold the integrity of her styling....
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    Location Information
    Lincolnwood, Illinois 60712
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Buffalo Grove
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Central Heating
    • Grill
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our beautiful single family home located in the Chicago suburbs of Buffalo Grove is quiet and spacious! We are 25 minutes from Six Flags Great America, 15 minutes from the convention centers in Schaumburg, 9 minutes to major corporations like Baxter, Walgreens, CVS and 45 minutes to Chicago...
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    Location Information
    Buffalo Grove, Lake County 60089
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    Evanston, IL
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hull Chateau is a delightful, bright, relaxed place. Hull Chateau is quiet and private. Guests will feel like home. The entire house is open to guests. We Provide the guests the experience of a 'Home away from home'. Hull Chateau is in a great Evanston neighborhood. Quiet, peaceful, and...
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    Location Information
    Evanston, Illinois 60202
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    Lake Zurich
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Parking
    • Balcony
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You have a private studio apartment all to yourself (about the size of a typical motel room). I'm always working on decor & improvements, so it might be even more attractive when you arrive! I have this listed for 1 person but if you're comfortable sharing the bed with your travel companion that's...
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    Location Information
    Lake Zurich, Lake County 60047
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Highwood
    4 Bedrooms, 5 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sensational Chicago area home, in northern suburbs. 10 minute walk to Lake Michigan! Location! Location!! In the North Shore area of Chicago. Private back yard lined with trees and shrubs. Big outdoor island with a grill and patio furniture for your lounging. Spend time in beautiful city of...
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    Location Information
    Highwood, Lake County 60040
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 6
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    Lincolnwood, IL
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This incredibly lavish 2BR apartment boasts an array of antique furniture and fixtures. Rich wall paneling, sculptures, and fine furnishings make this Andersonville getaway truly unique. Step back in time while enjoying the modern convenience of a full contemporary kitchen. Wrigleyville is a...
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    Location Information
    Lincolnwood, Illinois 60640
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Evanston, IL
    1 Bedroom, 2 Bathrooms, Sleeps 3 Quick View
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    Amenities & Details
    • Private Yard
    • Internet Access
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Pinewoods Retreat is home to a small artist community including musicians, painters and acrobats. Here you will find an eclectic yet quiet escape from the fast paced city. We take great pride in the peaceful environment that we have created here and welcome you to share in our retreat. Please...
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    Location Information
    Evanston, Illinois 60203
    Private Room - 1 Bedroom, 2 Bathrooms, Sleeps 3
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    Lincolnwood, IL
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Built in 1919, this elegant 4BR/3.5BA has been beautifully updated and features gleaming hardwood floors, stylish furniture, and tasteful art. Spread out in 3,300 square feet of comfortable living space, including two living rooms and a fenced backyard. A fantastic location in Albany Park puts you...
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    Location Information
    Lincolnwood, Illinois 60625
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Lincolnwood, IL
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Balcony
    • Terrace
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Excitement bustles around Chicago as you approach this 2-bedroom, 2.5-bathroom vacation rental townhome! With room to host 4 on beds and other sleeping arrangements, this 3-story home offers 2 living areas, a gourmet kitchen, 2-car garage, and sophisticated decor, creating a luxury accommodation in...
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    Location Information
    Lincolnwood, Illinois 60660
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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