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Winnetka Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Winnetka vacation rentals

Breakfast, lunch and dinner served

1. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (205 reviews)
"Absolutely amazing property."
United States
Nuriye
The price is AED 569
AED 651 total
includes taxes & fees
16 Aug - 17 Aug
The Gem Museum Suites
Full-size fridge, microwave, oven, stovetop

2. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (516 reviews)
"We only stayed one night but we definitely want to go back and stay at least two nights. It really was beautiful, clean and very secure."
United States
Martha
The price is AED 865
AED 1,106 total
includes taxes & fees
31 Aug - 1 Sep
Level Chicago – Old Town
Lake

3. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
7.8 out of 10, Good, (13 reviews)
"Great location and super clean!"
United States
Erica
The price is AED 751
AED 1,111 total
includes taxes & fees
7 Sep - 8 Sep
Kasa Lake Shore Chicago
Premium Apartment, 1 Bedroom | Living area | 55-inch flat-screen TV with cable channels, TV

4. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,259 reviews)
"The room and building were beautiful and located in a great place."
United States
Ryan
The price is AED 555
AED 760 total
includes taxes & fees
30 Aug - 31 Aug
Sentral Michigan Avenue
Living area

5. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
8.6 out of 10, Excellent, (49 reviews)
"would not recommend"
United States
heidi
The price is AED 802
AED 941 total
includes taxes & fees
8 Sep - 9 Sep
Wrigleyville Suites
Apartment, Private Bathroom | Lounge

6. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (11 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is AED 816
AED 1,342 total
includes taxes & fees
23 Aug - 24 Aug
At Home in Oak Park
Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Lounge

7. Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is AED 859
AED 1,391 total
includes taxes & fees
18 Aug - 19 Aug
Historic Oak Park Home
Studio | Living area

8. Ground Floor Studios in Chicago by 747 Lofts

Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
West Town
8.6 out of 10, Excellent, (25 reviews)
"It’s a really nice place. Its quite a distance from downtown Chicago. But it’s like 3 minutes from Chicago Blue line and a minute away from the bus station. Food is not a problem since there is a Korean grocery nearby. There is also a nearby Catholic church. The ameneties in this loft hotel is complete so if you are looking for a budget style trip and accommodation, I highly recommend this place."
United States
Joel
The price is AED 489
AED 692 total
includes taxes & fees
23 Aug - 24 Aug
Ground Floor Studios in Chicago by 747 Lofts
House (3 Bedrooms) | Interior

9. 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 AED 889
AED 1,744 total
includes taxes & fees
20 Aug - 21 Aug
Classic Forest Park Foursquare < 1 Mi to Blue Line
Studio | Exterior

10. Chicago Third Floor Studio by 747 Lofts

Chicago Third Floor Studio by 747 Lofts
2.0 star property
West Town
9.8 out of 10, Exceptional, (7 reviews)
"Clean, easy to check in, all the household items you’d expect"
United States
Jason
The price is AED 492
AED 990 total
includes taxes & fees
18 Aug - 19 Aug
Chicago Third Floor Studio 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

Congress Plaza Hotel

Congress Plaza Hotel

8/10 Good
"Great location, hotel staff were friendly and helpful. Only complaint is the noise. I slept with earplugs in."
Danielle 4-night trip
Posted less than an hour ago
Congress Plaza Hotel

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 are some of the best vacation rentals in Winnetka?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: Visitors like this Winnetka vacation home rental. It is located in the city center and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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 United Center.

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.