Search Holiday Rentals in Winnetka

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Check prices for these dates

In two weeks
23 Jan - 25 Jan
In two months
6 Mar - 8 Mar
In three months
3 Apr - 5 Apr
In four months
1 May - 3 May

Our top choices for Winnetka holiday rentals

Indoor pool
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1,039 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 Rp1.842.044
Rp2.655.354 total
includes taxes & fees
13 Jan - 14 Jan
Sentral Michigan Avenue
Lounge
Kasa River North Chicago

Aparthotel in Downtown Chicago

Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (182 reviews)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Full-sized fridge, microwave, oven, stovetop
Level Chicago – Old Town

Aparthotel in Downtown Chicago

Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (408 reviews)
"Great location, clean room and friendly staff!"
United States
Scott
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

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

10/10 Excellent
"London House was FANTASTIC!! Great service from checkin to check out! Beautiful luxury hotel!!"
Lisa 1-night trip
Posted 11 hours ago
LondonHouse Chicago, Curio Collection by Hilton

Find out more about Winnetka

Search for holiday rentals in Winnetka on Expedia.co.id! 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 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.