Winnetka Vacation Rentals

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Check prices for these dates

Tonight
Jan 9 - Jan 10
Tomorrow
Jan 10 - Jan 11
This weekend
Jan 9 - Jan 11
Next weekend
Jan 16 - Jan 18

Our top choices for Winnetka vacation rentals

Indoor pool
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1,037 reviews)
"Place was very nice and clean. We enjoyed the stay there. Will book it again when we come back to Chicago visit again. "
United States
Khalid
The price is NT$3,463
NT$4,993 total
includes taxes & fees
Jan 11 - Jan 12
Sentral Michigan Avenue
Lounge
Kasa River North Chicago

Aparthotel in Downtown Chicago

Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (182 reviews)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Full-size fridge, microwave, oven, stovetop
Level Chicago – Old Town

Aparthotel in Downtown Chicago

Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (408 reviews)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town
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 Winnetka Hotel Reviews

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

10/10 Excellent
"This hotel was beautiful Staff was friendly Centrally located Awesome "
evelyn m 2-night trip
Posted 9 hours ago
LondonHouse Chicago, Curio Collection by Hilton

Find out more about Winnetka

Search for holiday rentals in Winnetka on Expedia! You can easily find your home rentals, villas, holiday apartments in Winnetka using one of the methods below:

  • View our selection of featured holiday rentals in Winnetka
  • Use the map to find apartments and other holiday homes in the Winnetka neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winnetka while they last

Look no further and take a look at our great range of rental properties in Winnetka!

Frequently asked questions

Can I find vacation rentals in Winnetka?

Yes, we offer vacation rentals in Winnetka near Chocolate Box, or you can go with a more remote option if you'd like a relaxing place to stay. Winnetka is known for its shopping and forests. Make sure you have time to check out the sporting events and restaurants during your trip.

What can I see and do in Winnetka?

Lake Michigan and Elder Lane Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Chocolate Box. While in the area, you can also visit popular places like Wrigley Field and Naval Base Great Lakes.

What are vacation rentals like in Winnetka?

Vacation rentals are private accommodations you can stay in for a couple days or more in Winnetka. Vacation rentals feature extras such as hot tubs, fire pits, and patios so your stay will be comfortable. If you're concerned about cleanliness, a vacation rental can provide a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for family trips.