Winnetka Vacation Rentals

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Check prices for these dates

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

Our top choices for Winnetka vacation rentals

Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1036)
"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 P6,863
P9,791 total
includes taxes & fees
Jan 11 - Jan 12
Sentral Michigan Avenue
Exterior
Chicago luxury home suites

Chicago luxury home suites

Chicago luxury home suites
2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (4)
"Amazing stay! The location is very central and close to everything. The room was spotless, and the mattress was very comfortable. I really appreciated that the property is pet friendly. I was able to bring my dog along, which made the trip even better. The view was absolutely stunning. The hosts were very responsive and helpful throughout our stay. Highly recommend!"
Canada
Alex
The price is P5,861
P6,881 total
includes taxes & fees
Jan 8 - Jan 9
Chicago luxury home suites
Lounge
Kasa River North Chicago

Kasa River North Chicago

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

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (408)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town
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
Near North Side
9.4 out of 10, Exceptional, (10)
"Good for family, enjoyed the stay"
United States
Karthik
ENVITAE Hotel 4 Bedroom Luxury Apartments
Living area
Wrigleyville Suites

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.6 out of 10, Exceptional, (27)
"Nice place "
United States
Barry
The price is P8,777
P10,304 total
includes taxes & fees
Jan 11 - Jan 12
Wrigleyville Suites
Breakfast, lunch, dinner served; Greek cuisine
The Gem Museum Suites

The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (103)
"This is a fantastic hotel with super friendly staff"
United States
German
The price is P10,764
P12,322 total
includes taxes & fees
Jan 8 - Jan 9
The Gem Museum 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

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"Excellent rooms! Very roomy! Wonderful location. Will stay here again. "
Jasmine 4-night trip
Posted 7 hours ago
Hilton Chicago/Magnificent Mile Suites

Find out more about Winnetka

Search for holiday rentals in Winnetka on Expedia! 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 vacation rentals in Winnetka?

Yes, we offer vacation rentals in Winnetka near Chocolate Box, or you can go with a more remote option if you'd like a relaxing place to 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 like Wrigley Field and Naval Base Great Lakes.

What are vacation rentals like in Winnetka?

Vacation rentals are private accommodations you can stay in for a couple days or more in Winnetka. Vacation rentals feature extras such as hot tubs, fire pits, and patios so your stay will be comfortable. If you're concerned about cleanliness, a vacation rental can provide a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for family trips.