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Winnetka Vacation Rentals

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Winnetka vacation rentals

Lake

Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
The price is ₩391,196
₩554,533 total
includes taxes & fees
Aug 4 - Aug 5
Kasa Lake Shore Chicago
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,208 reviews)
"Clean room, great staff, family-friendly, pet-friendly, and great rooms with a kitchen and wonderful showers. Great location!"
United States
Alessandra
The price is ₩305,659
₩402,961 total
includes taxes & fees
Aug 9 - Aug 10
Sentral Michigan Avenue
Full-size fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (500 reviews)
"Very clean and loved the location and amenities with the store on the first floor was fantastic"
United States
Kimberly
The price is ₩526,766
₩655,489 total
includes taxes & fees
Aug 9 - Aug 10
Level Chicago – Old Town
Breakfast, lunch and dinner served

The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (155 reviews)
"The cook to order breakfast was great."
United States
Megan
The price is ₩283,015
₩324,000 total
includes taxes & fees
Aug 9 - Aug 10
The Gem Museum Suites
Design Apartment, Private Bathroom (The Oak Park Loft) | Exterior

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (6 reviews)
The price is ₩242,526
₩444,714 total
includes taxes & fees
Jul 13 - Jul 14
The Oak Park Loft
Dining room

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (816 reviews)
The price is ₩467,178
₩636,731 total
includes taxes & fees
Jul 21 - Jul 22
Kasa Magnificent Mile Chicago
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

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

10/10 Excellent
"Excellent"
Pavan Kumar 1-night trip
Posted 1 hour ago
Hyatt Regency O'Hare Chicago

Find out more about Winnetka

Search for Vacation rentals in Winnetka on Expedia.co.uk! You can easily find your home rentals, villas, Vacation apartments in Winnetka using one of the methods below:

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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 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 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 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.