Winnetka Vacation Rentals

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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Winnetka holiday rentals

Lounge

Aparthotel in Downtown Chicago

Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (183 reviews)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Full-sized fridge, microwave, oven, stovetop

Aparthotel in Downtown Chicago

Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (411 reviews)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town
Indoor pool

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1,050 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 RM445
RM641 total
includes taxes & fees
19 Jan - 20 Jan
Sentral Michigan Avenue
View from property

ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments
2.0 star property
9.4 out of 10, Exceptional, (10 reviews)
"Good for family, enjoyed the stay"
United States
Karthik
ENVITAE Hotel 4 Bedroom Luxury Apartments
Breakfast, lunch, dinner served; Greek cuisine

Aparthotel in Downtown Evanston

The Gem Museum Suites
3.5 star property
9.4 out of 10, Exceptional, (103 reviews)
"This is a fantastic hotel with super friendly staff"
United States
German
The price is RM738
RM845 total
includes taxes & fees
25 Jan - 26 Jan
The Gem Museum Suites
Interior

Aparthotel in West Town

River West, Third Floor Chicago by 747 Lofts
2.0 star property
9.0 out of 10, Wonderful, (17 reviews)
"Loved the space and location "
United States
Caroline
The price is RM302
RM1,401 total
includes taxes & fees
25 Jan - 26 Jan
River West, Third Floor Chicago by 747 Lofts
Living area

Aparthotel in Lakeview

Wrigleyville Suites
2.0 star property
9.6 out of 10, Exceptional, (27 reviews)
"Nice place "
United States
Barry
The price is RM603
RM707 total
includes taxes & fees
19 Jan - 20 Jan
Wrigleyville Suites
Interior

Cottage in Forest Park

Classic Forest Park Foursquare < 1 Mi to Blue Line
3.0 star property
Classic Forest Park Foursquare < 1 Mi to Blue Line
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 Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"This place was perfect!!! Soo so so much space for our family. The bathroom was actually enormous…like TWO separate sinks even and huge soak tub and huge wall in shower!!! The hotel was located in such an amazing area that made it so convenient for us to check out everything downtown Chicago!! Staff was phenomenal! Great great stay and would highly recommend to anyone! We will return!!! "
Brian 3-night trip
Posted 20 hours ago
The Royal Sonesta Chicago Downtown

Find out more about 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
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  • 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 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 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.