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Check prices for these dates

Tonight
8 Dec - 9 Dec
Tomorrow
9 Dec - 10 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

Top Holiday Rentals in Winnetka

Indoor pool
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

4.0 star property
9.2 out of 10, Wonderful, (1001)
"Beautiful view, and a very nice condo. "
United States
Tiffanie
The price is ₹10,633
₹15,122 total
includes taxes & fees
24 Dec - 25 Dec
Sentral Michigan Avenue
Front of property – evening/night
Level Chicago – Old Town

Aparthotel in Downtown Chicago

4.0 star property
9.0 out of 10, Wonderful, (395)
"Clean room cool staff enjoyed my stay will come stay again. "
United States
Donald
Level Chicago – Old Town
Free WiFi, bed sheets
Chicago luxury home suites

Aparthotel in Downtown Chicago

2.0 star property
7.4 out of 10, Good, (3)
"Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job."
Canada
pouya
The price is ₹11,846
₹13,905 total
includes taxes & fees
16 Dec - 17 Dec
Chicago luxury home suites
Business centre
Kasa River North Chicago

Aparthotel in Downtown Chicago

4.0 star property
9.6 out of 10, Exceptional, (181)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Studio | Exterior
Chicago Third Floor Studio by 747 Lofts

Aparthotel in West Town

2.0 star property
9.6 out of 10, Exceptional, (5)
"Cute little studio that was clean. There was a nice size kitchen and was close to our activities in the West loop of Chicago. There was also assistance with parking located in the lofts."
United States
Jennifer
The price is ₹5,246
₹19,574 total
includes taxes & fees
10 Dec - 11 Dec
Chicago Third Floor Studio by 747 Lofts
Living area
Wrigleyville Suites

Aparthotel in Lakeview

2.0 star property
9.6 out of 10, Exceptional, (26)
"Excellent location and very clean! Would stay again!"
United States
Jacob
The price is ₹7,134
₹8,375 total
includes taxes & fees
10 Dec - 11 Dec
Wrigleyville Suites
Suite, 2 Bedrooms, Kitchen (Three Beds, Washer/Dryer) | Private kitchen | Full-sized fridge, microwave, stovetop, dishwasher
The Gem Museum Suites

Aparthotel in Downtown Evanston

3.5 star property
9.4 out of 10, Exceptional, (98)
"Great stay. The studio is small but has everything necessary."
United States
Julia
The price is ₹16,361
₹18,730 total
includes taxes & fees
15 Dec - 16 Dec
The Gem Museum Suites
Classic Apartment | Private kitchen
Stylish Apartment near Chicago Downtown

Aparthotel in Bridgeport

2.0 star property
The price is ₹21,849
₹34,945 total
includes taxes & fees
14 Dec - 15 Dec
Stylish Apartment near Chicago Downtown
House (3 Bedrooms) | Interior
Classic Forest Park Foursquare < 1 Mi to Blue Line

Cottage in Forest Park

3.0 star property
The price is ₹14,219
₹37,121 total
includes taxes & fees
11 Dec - 12 Dec
Classic Forest Park Foursquare < 1 Mi to Blue Line
Studio | Exterior
Ground Floor Studios in Chicago by 747 Lofts

Aparthotel in West Town

2.0 star property
9.0 out of 10, Wonderful, (21)
"The stay lacked in shelf space as well as other amenities that could be useful. "
United States
Zugeily
The price is ₹5,246
₹11,953 total
includes taxes & fees
10 Dec - 11 Dec
Ground Floor Studios in Chicago by 747 Lofts
Studio | Private kitchen | Fridge, oven, coffee/tea maker, toaster
Chicago Second Floor Studio by 747 Lofts

Aparthotel in West Town

2.0 star property
8.8 out of 10, Excellent, (13)
"Great location, convenient to downtown and blue line to airport. Everything necessary in unit, comfortable temperature and full kitchen with unique grocery store nearby."
United States
Barbara
The price is ₹5,246
₹11,953 total
includes taxes & fees
11 Dec - 12 Dec
Chicago Second Floor Studio by 747 Lofts
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

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

10/10 Excellent
"Very nice hotel stay. Would definitely go back "
Rahul 6-night trip
Posted 20 hours ago
The Whitehall Hotel, BW Premier Collection

Find out more about Winnetka

Holiday Rentals in Winnetka

Search for holiday rentals in Winnetka on Expedia.co.uk! 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 holiday rentals in Winnetka?

Yes, there are holiday rentals in Winnetka close to Chocolate Box, or you can select a more secluded option if you're looking for a relaxing 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 such as Wrigley Field and Naval Base Great Lakes.

What are holiday rentals like in Winnetka?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winnetka. Holiday rentals offer extras like laundry facilities and kitchens so you'll have everything you need. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a family trip or a small group gathering.