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Winnetka Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Winnetka vacation rentals

A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

1. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (270 reviews)
"Really helpful staff, really nice rooms."
United States
Archita
The price is NT$5,992
NT$6,860 total
includes taxes & fees
Sep 28 - Sep 29
The Gem Museum Suites
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

2. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
7.8 out of 10, Good, (58 reviews)
"We had a great stay! Perfect location for cubs games and hanging out in wrigleyville."
United States
Kate
The price is NT$5,128
NT$6,020 total
includes taxes & fees
Sep 28 - Sep 29
Wrigleyville Suites

3. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (39 reviews)
"Great location and room"
United States
Miriam
The price is NT$6,302
NT$9,385 total
includes taxes & fees
Sep 27 - Sep 28
Kasa Lake Shore Chicago
A modern building with the name 'SENIORAL' prominently displayed on the facade.

4. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,341 reviews)
"Great venue"
United States
Arthur Noel
The price is NT$5,384
NT$7,254 total
includes taxes & fees
Sep 27 - Sep 28
Sentral Michigan Avenue
A building with a white exterior and a tree with white blossoms in front.

5. Historic Oak Park Residence

Historic Oak Park Residence
2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"The house is in an amazing neighborhood, easy access to subway, extremely clean and great follow-up and follow through communication with owner!"
United States
Ann-Marie
The price is NT$7,654
NT$12,296 total
includes taxes & fees
Oct 21 - Oct 22
Historic Oak Park Residence
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

6. Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
3.0 star property
Forest Park
The price is NT$7,703
NT$15,114 total
includes taxes & fees
Sep 27 - Sep 28
Classic Forest Park Foursquare < 1 Mi to Blue Line
A modern kitchen with a large island, bar stools, and a city view.

7. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (529 reviews)
"Location and facility was very nice"
United States
Brian
The price is NT$9,507
NT$11,946 total
includes taxes & fees
Sep 27 - Sep 28
Level Chicago – Old Town
A spacious living room with a grand piano, a comfortable sofa, and a dining area with a chandelier.

8. Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
8.8 out of 10, Excellent, (6 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is NT$6,961
NT$11,503 total
includes taxes & fees
Oct 14 - Oct 15
Historic Oak Park Home
A modern building with large glass windows, surrounded by a grassy area with trees and a pathway.

9. The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.2 out of 10, Wonderful, (7 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is NT$5,653
NT$10,006 total
includes taxes & fees
Oct 13 - Oct 14
The Oak Park Loft

10. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is NT$7,091
NT$11,653 total
includes taxes & fees
Oct 6 - Oct 7
At Home in Oak Park
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
"Cool"
Carlos Joel 2-night trip
Posted 1 hour ago
Congress Plaza Hotel

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
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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 near the most popular attractions in Winnetka, or you can go with a more remote option if you're looking for relaxation. 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 get outside and enjoy nature. While in the area, you can also visit popular places like Wrigley Field and Navy Pier.

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.