Search Holiday Rentals in Winnetka

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Check prices for these dates

Tonight
13 Jan - 14 Jan
Tomorrow
14 Jan - 15 Jan
This weekend
16 Jan - 18 Jan
Next weekend
23 Jan - 25 Jan

Our top choices for Winnetka holiday rentals

Lounge
Kasa River North Chicago

Aparthotel in Downtown Chicago

Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (183 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, (411 reviews)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town
Indoor pool
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1,046 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 2.880.291 ₫
4.152.013 ₫ total
includes taxes & fees
21 Jan - 22 Jan
Sentral Michigan Avenue
View from property
ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments
2.0 star property
9.4 out of 10, Exceptional, (10 reviews)
"Good for family, enjoyed the stay"
United States
Karthik
ENVITAE Hotel 4 Bedroom Luxury Apartments
Breakfast, lunch, dinner served; Greek cuisine
The Gem Museum Suites

Aparthotel in Downtown Evanston

The Gem Museum Suites
3.5 star property
9.4 out of 10, Exceptional, (103 reviews)
"This is a fantastic hotel with super friendly staff"
United States
German
The price is 4.775.704 ₫
5.467.226 ₫ total
includes taxes & fees
14 Jan - 15 Jan
The Gem Museum Suites
Interior
River West, Third Floor Chicago by 747 Lofts

Aparthotel in West Town

River West, Third Floor Chicago by 747 Lofts
2.0 star property
9.0 out of 10, Wonderful, (17 reviews)
"Loved the space and location "
United States
Caroline
The price is 1.952.575 ₫
9.068.059 ₫ total
includes taxes & fees
25 Jan - 26 Jan
River West, Third Floor Chicago by 747 Lofts
Living area
Wrigleyville Suites

Aparthotel in Lakeview

Wrigleyville Suites
2.0 star property
9.6 out of 10, Exceptional, (27 reviews)
"Nice place "
United States
Barry
The price is 3.900.501 ₫
4.578.798 ₫ total
includes taxes & fees
15 Jan - 16 Jan
Wrigleyville Suites
House (3 Bedrooms) | Interior
Classic Forest Park Foursquare < 1 Mi to Blue Line

Cottage in Forest Park

Classic Forest Park Foursquare < 1 Mi to Blue Line
3.0 star property
The price is 4.150.502 ₫
10.835.700 ₫ total
includes taxes & fees
14 Jan - 15 Jan
Classic Forest Park Foursquare < 1 Mi to Blue Line
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

Eurostars Magnificent Mile

Eurostars Magnificent Mile

10/10 Excellent
"Clean"
Javier 1-night trip
Posted 10 hours ago
Eurostars Magnificent 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 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.