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Tonight
22 Oct - 23 Oct
Tomorrow
23 Oct - 24 Oct
This weekend
24 Oct - 26 Oct
Next weekend
31 Oct - 2 Nov

Top Holiday Rentals in Winnetka

Indoor pool
Sentral Michigan Avenue
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (961)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is ₹11,792
₹16,423 total
includes taxes & fees
10 Nov - 11 Nov
Sentral Michigan Avenue
Front of property – evening/night
Level Chicago – Old Town
Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (370)
"Friendly staff and great amenities "
United States
Bryan
The price is ₹18,028
₹23,126 total
includes taxes & fees
11 Nov - 12 Nov
Level Chicago – Old Town
50-inch flat-screen TV with digital channels, TV
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
3.5 star property
8.2 out of 10, Very good, (185)
"Place was amazing! Very centralized, all sorts of restaurants nearby, and right next to the CTA Trains which is AWESOME!"
United States
Alexander
The price is ₹10,389
₹12,196 total
includes taxes & fees
10 Nov - 11 Nov
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Business centre
Kasa River North Chicago
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (174)
"This place has everything for a multi-night stay."
United States
Dane
Kasa River North Chicago
Business Apartment, City View | Private kitchen | Fridge, microwave, oven, stovetop
4BR Corporate Suite Central and Modern
4BR Corporate Suite Central and Modern
2.0 star property
10.0 out of 10, Exceptional, (4)
"We loved at our stay at this property. It was one of the best stays we have had on vacation."
United States
Javeria
The price is ₹12,347
₹32,972 total
includes taxes & fees
29 Oct - 30 Oct
4BR Corporate Suite Central and Modern
Studio | Private kitchen | Fridge, oven, coffee/tea maker, toaster
River West, Third Floor Chicago by 747 Lofts
River West, Third Floor Chicago by 747 Lofts
2.0 star property
9.0 out of 10, Wonderful, (17)
"Overall solid property, I will return."
United States
Fletcher
The price is ₹14,461
₹31,605 total
includes taxes & fees
31 Oct - 1 Nov
River West, Third Floor Chicago by 747 Lofts
1 bedroom, individually furnished, desk, iron/ironing board
Sonder by Marriott Bonvoy The Opal Apartments River North
Sonder by Marriott Bonvoy The Opal Apartments River North
3.5 star property
8.4 out of 10, Very good, (54)
"Place was in a great location close to good restaurants "
United States
Charles
The price is ₹10,389
₹12,196 total
includes taxes & fees
4 Nov - 5 Nov
Sonder by Marriott Bonvoy The Opal Apartments River North
Living area
Wrigleyville Suites
Wrigleyville Suites
2.0 star property
9.6 out of 10, Exceptional, (24)
"The entirety of my experience was excellent. Thank you!"
United States
Julian
The price is ₹11,713
₹18,146 total
includes taxes & fees
25 Oct - 26 Oct
Wrigleyville Suites
Fridge, microwave, oven, stovetop
Chicago luxury home suites
Chicago luxury home suites
2.0 star property
The price is ₹85,734
₹100,643 total
includes taxes & fees
24 Oct - 25 Oct
Chicago luxury home suites
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

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"We had 4 adults in the Family Suite plenty of room. Could use larger TV's. We requested more towels and coffee and were delivered promptly."
WILLIAM 3-night trip
Posted 1 day ago
Congress Plaza Hotel

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.