Winnetka Holiday Rentals

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Check prices for these dates

In two weeks
24 Apr - 26 Apr
In two months
5 Jun - 7 Jun
In three months
3 Jul - 5 Jul
In four months
31 Jul - 2 Aug

Our top choices for Winnetka holiday rentals

Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,129 reviews)
"Clean spacious my go to vacation spot all year around "
United States
xavier
The price is S$238
includes taxes & fees
14 Apr - 15 Apr
Sentral Michigan Avenue
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (188 reviews)
"Great place! Would definitely stay again!"
United States
Katherine
The price is S$347
includes taxes & fees
30 Apr - 1 May
Kasa River North 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.
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Top Winnetka Hotel Reviews

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

8/10 Good
"I enjoyed my stay. "
RAYVYNN 3-night trip
Posted 1 hour ago
Aloft Chicago Mag Mile

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.