Winnetka Holiday Rentals

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Check prices for these dates

In two weeks
12 Dec - 14 Dec
In two months
23 Jan - 25 Jan
In three months
20 Feb - 22 Feb
In four months
20 Mar - 22 Mar

Holiday Rentals in Winnetka

Indoor pool
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

4.0 star property
9.2 out of 10, Wonderful, (994)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is S$192
includes taxes & fees
7 Dec - 8 Dec
Sentral Michigan Avenue
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago

Aparthotel in Downtown Chicago

4.0 star property
9.2 out of 10, Wonderful, (633)
"Room was very nice, location was wonderful."
United States
Nicholas
Kasa Magnificent Mile Chicago
Front of property – evening/night
Level Chicago – Old Town

Aparthotel in Downtown Chicago

4.0 star property
9.0 out of 10, Wonderful, (388)
"Property was clean, centrally located with wonderful staff. Will definitely stay again."
United States
Michelle
Level Chicago – Old Town
Balcony
Kasa South Loop Chicago

Aparthotel in Downtown Chicago

4.0 star property
9.4 out of 10, Exceptional, (377)
"An excellent place to stay in Chicago downtown."
United States
ABDULHAFEEZ
Kasa South Loop Chicago
Front of property
The Neighborhood Hotel-Little Italy

Aparthotel in Near West Side

4.0 star property
9.6 out of 10, Exceptional, (221)
"Staff was courteous. Great location."
United States
Pamela
The Neighborhood Hotel-Little Italy
Business centre
Kasa River North Chicago

Aparthotel in Downtown Chicago

4.0 star property
9.4 out of 10, Exceptional, (180)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Living area
Wrigleyville Suites

Aparthotel in Lakeview

2.0 star property
9.6 out of 10, Exceptional, (26)
"Excellent location and very clean! Would stay again!"
United States
Jacob
The price is S$136
includes taxes & fees
1 Dec - 2 Dec
Wrigleyville Suites
Private kitchen
The Gem Museum Suites

Aparthotel in Downtown Evanston

3.5 star property
9.4 out of 10, Exceptional, (97)
"Great stay. The studio is small but has everything necessary."
United States
Julia
The price is S$266
includes taxes & fees
30 Nov - 1 Dec
The Gem Museum Suites
Free WiFi, bed sheets
Chicago luxury home suites

Aparthotel in Downtown Chicago

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job."
Canada
pouya
The price is S$269
includes taxes & fees
27 Nov - 28 Nov
Chicago luxury home suites
Private kitchen
Stylish Apartment near Chicago Downtown

Aparthotel in Bridgeport

2.0 star property
The price is S$506
includes taxes & fees
2 Dec - 3 Dec
Stylish Apartment near Chicago Downtown
Interior
Art Villa

Aparthotel in West Town

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
United States
tomonobu
Art Villa
Exterior
Ground Floor Studios in Chicago by 747 Lofts

Aparthotel in West Town

2.0 star property
9.0 out of 10, Wonderful, (21)
"The stay lacked in shelf space as well as other amenities that could be useful. "
United States
Zugeily
Ground Floor Studios in Chicago by 747 Lofts
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
"The room had a beautiful view!! It was very clean, and cleaned everyday. The staff was always happy and very helpful. Definitely recommend this hotel if you want to stay downtown. "
Andrea 4-night trip
Posted 7 hours ago
The Royal Sonesta Chicago Downtown

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.