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Holiday Homes in Winnetka

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    Don't let other travellers get your favourite Winnetka area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 18 Rentals in Winnetka
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    Just north of Chicago1 / 8
    (19)Excellent
    Winnetka
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    The following rentals are within 25 kilometres of Winnetka.
    Beautifully Remodeled 3 BR Townhouse near Chicago1 / 30
    (2)Excellent
    Wilmette
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Completely Remodeled 3-Bedroom House!1 / 27
    (3)Very good
    Wheeling
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Lincolnwood
    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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    60613, Lincolnwood, Illinois
    Condo/Apartment - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Handsome 3BR in Lake View by Sonder1 / 18
    (1)Excellent
    Lincolnwood
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Washer
    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 September 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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    60613, Lincolnwood, Illinois
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Lincolnwood
    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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    60618, Lincolnwood, Illinois
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    River Grove
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Parking
    • Cable/satellite TV
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    • Air Conditioning
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This property is a vacational rental house designed for short or long term stays with everything you need to call this your new home. The 8 key areas for your comfy stay include: 1. A snazzy living room 2. Dining room 3. Office with attached bathroom (bathtub included) 4. Full kitchen facility...
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    60171, River Grove, Illinois
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Lincolnwood
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • 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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    60712, Lincolnwood, Illinois
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Highland Park
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Wi-Fi
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    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We are offering up our entire full, finished basement suite. Located in the City of Highland Park, our large traditional brick home built in 2003 is in walking distance to the town, train and gorgeous Lake Michigan Beach. Within 5 minutes driving time, or by public shuttle, you can attend the...
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    Location Information
    60035, Highland Park, Lake County
    Private Room - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Evanston
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    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
    60202, Evanston, Illinois
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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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
    60089, Buffalo Grove, Lake County
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    Highwood
    4 Bedrooms, 5 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
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    • Private Garden
    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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    60040, Highwood, Lake County
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 6
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    Evanston
    1 Bedroom, 2 Bathrooms, Sleeps 3 Quick View
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    • Private Garden
    • Internet Access
    • Air Conditioning
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    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
    60203, Evanston, Illinois
    Private Room - 1 Bedroom, 2 Bathrooms, Sleeps 3
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    Lincolnwood
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    • Washer
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    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
    60640, Lincolnwood, Illinois
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Lincolnwood
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Cable/satellite TV
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    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
    60625, Lincolnwood, Illinois
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Norridge
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a clean, quiet and cozy garden apartment in an amazing area that is perfect whether you are venturing locally or traveling...
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    60634, Norridge, Illinois
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Lincolnwood
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • 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
    60660, Lincolnwood, Illinois
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Norridge
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a clean, quiet and cozy apartment in an amazing area that is perfect whether you are venturing locally or traveling downtown. Located off Irving and Cumberland you are within walking distance of multiple amazing bars and restaurants and a short drive from some of the best restaurants in the...
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    Location Information
    60706, Norridge, Illinois
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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