Vacation rentals in Winnetka

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Top-rated vacation rentals in Winnetka

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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