Vacation rentals in Winnetka

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Top-rated vacation rentals in Winnetka

Guests agree: these stays are highly rated for location, cleanliness, and more.

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SUPERHOST
Entire guest suite · Winnetka
Stay in a Historic Schoolhouse 15 minutes to NU!
It really was a Montessori schoolhouse! The famous teacher lived in your upstairs apartment. You are fifteen minutes to Northwestern and forty minutes to downtown Chicago with the train and bus on the same block. This is a child-friendly stay-your host has everything you need to keep the kids busy.
$139 per night
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Entire rental unit · Northbrook
✨ Guest Room with 1 King Bed + FREE Wifi at Renaissance Chicago North Shore Hotel
Welcome to Renaissance Chicago North Shore Hotel! We offer complimentary shuttle transportation within a 5 miles radius of the hotel! Spacious rooms and suites, curated amenities and an ideal location in Northbrook, IL combine for spectacular results at Renaissance Chicago North Shore Hotel. Ideally situated on the North Shore of Chicago, we offer an optimal location for guests visiting the area.
$121 per night
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SUPERHOST
Private room · Wilmette
(BR#1) Welcoming, warm & comfortable, 3 guests
Welcoming, warm & comfortable home, BR#1 for up to 3 guests. (LISTING #1 OF 3; see other listings for additional space.) Located close to Hwy 94. 10 miles from Chicago, close to beach & Wilmette, Evanston, Glenview, Skokie. You're welcome to use all the facilities - kitchen, bathrooms, TV, hi-speed Wifi, laundry & parking. Make your breakfast with supplied basics such as cereal, eggs, juice, tea & coffee. Really friendly small Yorkie-poo dog in the home. Meaningful conversation (if you want it).
$51 per night

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Other great vacation rentals in Winnetka

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Private room · Wilmette
Cozy, one-bedroom retreat
$40 per night
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SUPERHOST
Entire home · Wilmette
Unique porcelain-enamel steel panel "Lustron" home
$151 per night
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Entire rental unit · Evanston
Northwestern Themed 1bd Ryan Fields Stadium view !
$49 per night
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Entire rental unit · Highland Park
Highland Park Cozy Studio Apt Near Metra & Beach
$86 per night
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Private room · Des Plaines
Quiet. Pleasant. Enjoy a good night's Sleep!
$30 per night
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Private room · Evanston
I- Soothing Bedroom (1Queen Bed)
$45 per night
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SUPERHOST
Private room · Niles
Private, Furnished Bedroom in Chicago Suburb
$39 per night
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Private room · Highland Park
Stylish & comfy private bed, bath, & living room!
$51 per night
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SUPERHOST
Private room · Glenview
Upstairs Suite
$57 per night
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SUPERHOST
Private room · Wilmette
(BR#2) Welcoming, warm & comfortable, 2 guests
$49 per night
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SUPERHOST
Entire rental unit · Wilmette
1 Bedroom Wilmette Apartment steps away from metra
$175 per night
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Entire home · Wilmette
Elegant house with all comfort & fresh cool vibes
$303 per night
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