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Highland Park Holiday Rentals

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    Don't let other travellers get your favourite Highland Park area holiday 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 25 kilometres 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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    Mount Prospect, IL
    3 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Completely Remodeled 3-Bedroom House!1 / 27
    (1)Excellent
    Wheeling, IL
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Secure Parking
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • Grill
    • Washer
    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 August 2017
    We had a great time!! The area is clean, the neighborhood is quiet and very pleasant. We went as a family of 5 to visit my daughter who was in classes at the Naval Base in Great...
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    About this property
    Beautifully Remodeled 3-Bedroom House with new hardwood floor, gorgeous granite countertop kitchen, and contemporary furniture. Walk to grocery, shops and restaurants. Awesome location, just 1 min. to Metra station, 20 min. to O'Hare Airport, Lake Michigan & Ravinia Park, and a pleasant 30 min....
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    Wheeling, Illinois 60090
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Gurnee
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Parking
    • Air Conditioning
    • Patio
    • Grill
    • Washer
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay cool in this Smart, Connected, Air Conditioned, Completely remodeled and updated Home in Gurnee on 3/4 acre private wooded lot surrounded by large trees and flowers providing a calming and very private place to relax and unwind..Close to grocery stores (Jewel Osco 1/2 mile), great restaurants,...
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    Gurnee, Lake County 60031
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Lincolnwood, IL
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Balcony
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    • DVD Player
    • Internet Access
    • Washer
    • Hot Tub
    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 6 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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    Lincolnwood, Illinois 60660
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Stay and play like a local1 / 24
    (1)Excellent
    Lincolnwood, IL
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Parking
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Private Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 January 2018
    My family and I stayed at the property twice from Christmas Eve until January 7th, as my son was going through basic training at the Navy Recruit Training Center at Great Lakes...
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    About this property
    Stay and play like a Chicago local in our Northside home. With easy access to Ravenswood, Lincoln Square, Andersonville and Wrigleyville neighborhoods, your options are unlimited! Walk to Gompers Park play tennis or swim. get groceries at nearby Jewel, dine at authentic Mexican restaurants....
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    Location Information
    Lincolnwood, Illinois 60630
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Evanston, IL
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location, Location ,Location. Walk to many restaurants and stores. Take the Clark bus to Cubs Park. One mile to Foster Beach. Bikes for rent nearby. Great apartment to relax and sleep. This is a second floor walk up apartment. We are close to Lake Shore Drive. The CTA Red line, Berwyn stop is...
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    Evanston, Illinois 60640
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Highwood
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly remodeled 4,000 sq foot house near Lake Michigan and only a 10 minute walk to train with 45 minute ride downtown chicago! Private back yard with an outdoor large patio and designer furniture. Amazing north shore location! 2 car garage and a third additional pad for parking. Beautiful Fort...
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    Location Information
    Highwood, Lake County 60040
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    Evanston, IL
    1 Bedroom, 2 Bathrooms, Sleeps 3 Quick View
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    Amenities & Details
    • Private Garden
    • 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
    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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Just north of Chicago1 / 8
    (18)Excellent
    Winnetka, IL
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Washer
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    • Secure Parking
    • Patio
    • DVD Player
    • Shared Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 May 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 23 November 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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    Location Information
    Winnetka, Illinois 60093
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Lincolnwood, IL
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    My place is a short walk to Kimball CTA Brown Line, which will get you downtown in about 30 minutes. My place is good for couples, solo adventurers, and business travelers. One bedroom with TV, large living room with TV and wireless Bluetooth soundbar if you want to play music, nice kitchen with...
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    Location Information
    Lincolnwood, Illinois 60625
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Buffalo Grove
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Secure Parking
    • Air Conditioning
    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Classic clean one bedroom condo off 290 30 minutes to Chicago. Great restaurants just three blocks away Starbucks ,Walkerbrotuers , Jamessons char house etc.Private gated heated pool, reserved parking by condo ,Lake Arlington three blocks away where one may hike,surrounded by a beach oasis where...
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    Location Information
    Buffalo Grove, Lake County 60089
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Buffalo Grove
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • 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
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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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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