Winnetka Vacation Rentals

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Check prices for these dates

Tonight
Dec 16 - Dec 17
Tomorrow
Dec 17 - Dec 18
This weekend
Dec 19 - Dec 21
Next weekend
Dec 26 - Dec 28

Our top choices for Winnetka vacation rentals

Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1009)
"This place made a great landing spot for a holiday weekend w family. Clean, great location, loved the holiday decorations and indoor pool / outside hot tub. Will stay again! "
United States
Deidre
The price is ₩173,509
₩246,775 total
includes taxes & fees
Dec 22 - Dec 23
Sentral Michigan Avenue
Full-size fridge, microwave, oven, stovetop
Level Chicago – Old Town

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (401)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town
Lounge
Kasa River North Chicago

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (182)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Fridge, microwave, oven, stovetop
Chicago luxury home suites

Chicago luxury home suites

Chicago luxury home suites
2.0 star property
Downtown Chicago
7.4 out of 10, Good, (3)
"Do not book. This is a scam you will be asking to zelle a several hundred dollar security deposit after paying in full and before check in. You’ll receive sketchy FaceTime audio calls and messages from several different numbers requesting this. "
United States
Brooke
The price is ₩158,603
₩186,183 total
includes taxes & fees
Dec 18 - Dec 19
Chicago luxury home suites
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

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

10/10 Excellent
"Great friendy staff, Smooth Check-in Check-out Process and the view from the room was just stunning. "
Sneha 2-night trip
Posted 6 hours ago
Club Quarters Hotel Wacker at Michigan, Chicago

Find out more about Winnetka

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

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