Lodging Image

Search Holiday Rentals in Winnetka

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Winnetka holiday rentals

A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

1. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (292 reviews)
"Very charming hotel we really enjoyed having breakfast in the morning and ability to have a bottle of wine with dinner at Knight and our bag was very comfortable and nice having the ability to open the window and have some fresh air all in all very charming"
United States
Kathleen
The price is ₹18,396
₹21,060 total
includes taxes & fees
22 Nov - 23 Nov
The Gem Museum Suites
A modern building with the name 'SENIORAL' prominently displayed on the facade.

2. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,386 reviews)
"Perfect location to stay at if attending the bears games !"
United States
Jacob
The price is ₹13,528
₹15,880 total
includes taxes & fees
9 Nov - 10 Nov
Sentral Michigan Avenue
Lake

3. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (73 reviews)
"First time staying there and we absolutely loved our stay. We will definitely be going back."
United States
Iliana
The price is ₹14,204
₹21,611 total
includes taxes & fees
1 Nov - 2 Nov
Kasa Lake Shore Chicago
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winnetka Hotel Reviews

Eurostars Magnificent Mile

Eurostars Magnificent Mile

8/10 Good
"Lovely hotel in a great location, I stayed on the 23rd floor, the room was brilliant but the windows did not shield the sound of sirens all night!"
Stephen 5-night trip
Posted 4 hours ago
Eurostars Magnificent Mile

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 close to the most popular sights in Winnetka, 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 get outside and enjoy nature. While in the area, you can also visit popular places such as Wrigley Field and Navy Pier.

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.