Hotels in Winnetka

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Tonight
Dec 27 - Dec 28
Tomorrow
Dec 28 - Dec 29
Next weekend
Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11

Where to stay in Winnetka?

Cocktail bar
Freehand Chicago
Freehand Chicago
4.0 star property
8.0 out of 10, Very Good, (2659)
  • cleanliness
    Art Deco retreat in downtown Chicago with Red Line steps from your door.
The price is CNY410
CNY604 total
includes taxes & fees
Jan 19 - Jan 20, 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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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 Adagio Teas and Kohl Children's Museum, 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

Pendry Chicago

Pendry Chicago

10/10 Excellent
"Room was really clean and fresh"
an 2-night trip
Posted 17 hours ago
Pendry Chicago

Frequently asked questions

How much does a hotel room cost in Winnetka?
You can find top hotels in Winnetka from CNY671 with options to suit your budget and needs. If you're looking for an affordable hotel in Winnetka that meets all of your requirements, just sort hotels by "Price: low to high" after applying your filters when searching on Hotels.com.
How can I find deals and earn rewards at Winnetka hotels?
Discover great deals on Winnetka hotel stays with Hotels.com. It's also a good idea to look at hotel prices mid-week or during the low season as you're likely to find off-peak deals. If it's a spontaneous trip, check out our last-minute deals on Winnetka hotels.
Can I book Winnetka hotels with free cancellation?
In order to book a refundable Winnetka hotel, simply filter hotels by "Property cancellation options" and select "Fully refundable property". The majority of hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.
What are some popular hotels in central Winnetka?
For hotels in central Winnetka, check out Graduate by Hilton Evanston and Hilton Orrington / Evanston. Travelers love Graduate by Hilton Evanston for its location, as well as the restaurant, bar/lounge and 24-hour gym this hotel offers. Hilton Orrington / Evanston is another popular central hotel with a restaurant, a bar/lounge and a 24-hour gym. South Evanston and North Evanston are some of the most central neighborhoods for your Winnetka vacation.
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.

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