Winnetka Vacation Rentals

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Check prices for these dates

In two weeks
Dec 5 - Dec 7
In two months
Jan 16 - Jan 18
In three months
Feb 13 - Feb 15
In four months
Mar 13 - Mar 15

Vacation Rentals in Winnetka

Indoor pool
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

4.0 star property
9.2 out of 10, Wonderful, (987)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is P5,938
P8,700 total
includes taxes & fees
Dec 8 - Dec 9
Sentral Michigan Avenue
Free WiFi, bed sheets
Chicago luxury home suites

Aparthotel in Downtown Chicago

2.0 star property
10.0 out of 10, Exceptional, (1)
"This was Amazing stay I have ever had in my life. Wonderful host, super clean. Stunning views, close to everything that you would needed. "
New Zealand
Moha
The price is P17,679
P20,753 total
includes taxes & fees
Nov 23 - Nov 24
Chicago luxury home suites
Business center
Kasa River North Chicago

Aparthotel in Downtown Chicago

4.0 star property
9.4 out of 10, Exceptional, (179)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Front of property - evening/night
Level Chicago – Old Town

Aparthotel in Downtown Chicago

4.0 star property
9.0 out of 10, Wonderful, (384)
"Property was clean, centrally located with wonderful staff. Will definitely stay again."
United States
Michelle
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

Warwick Allerton - Chicago

Warwick Allerton - Chicago

10/10 Excellent
"yes"
João 5-night trip
Posted 1 hour ago
Warwick Allerton - Chicago

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 Maple Street 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.