Hotels in Winnetka

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Dec 24 - Dec 25
Tomorrow
Dec 25 - Dec 26
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Where to stay in Winnetka?

Cocktail bar
Freehand Chicago
Freehand Chicago
4.0 star property
8.0 out of 10, Very Good, (2658)
The price is $59
$86 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Freehand Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Budget hotels in Winnetka and vicinity

Cocktail bar
Freehand Chicago

Freehand Chicago

Freehand Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very Good, (2658)
The price is $59
$86 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Freehand Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all budget hotels

Top landmarks in Winnetka

Chocolate Box

Chocolate Box is in the heart of Winnetka, so why not stop by during your stay. Why not take a stroll along the beaches and watch the sunset while you're here? If you have fun at Chocolate Box, you'll love Wagner Farm and Adagio Teas, both located nearby.
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Elder Lane Beach

When the beach is calling your name, you might want to head down to Elder Lane Beach, located 1.2 mi (2 km) from central Winnetka. If you want to continue walking by the waves, head to Kenilworth Beach located nearby.
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Learn more about Winnetka

Winnetka is well-known for its attractions such as Lake Michigan and Elder Lane Beach.

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Stinson Memorial Library Anna Illinois Listed on the National Register Funded by Anna businessman Robert Burns Stinson, designed by Walter Burley Griffin who studied under Frank Lloyd Wright.

Check out reviews of Winnetka hotels guests love

Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

10/10 Excellent
"Room was clean, staff amazing and just an overall great place to stay. "
Jerome 2-night trip
Posted 1 day ago
Holiday Inn Chicago Dwtn - The Mart by IHG

Frequently asked questions

Can I book refundable accommodations in Winnetka?
If you need the flexibility to change your plans to Winnetka, most accommodations offer refundable* bookable rates. You can see these properties by searching our site and using the "fully refundable" filter to narrow down the results.
What will the weather in Winnetka be like during my visit?
The warmest months in Winnetka are usually July and August with an average temp of 70°F. January and February are the chilliest months when the average temp is 30°F. The rainiest months are May and June.
Why should I book my Winnetka hotel through Hotels.com?
There are plenty of reasons to book your Winnetka travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.