Winnetka Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Winnetka holiday rentals

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1,039 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 HK$855
HK$1,232 total
includes taxes & fees
12 Jan - 13 Jan
Sentral Michigan Avenue

Apartment in Downtown Chicago

Gold Coast Living: Modern Studio Unit
10.0 out of 10, Exceptional, (5 reviews)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is HK$538
HK$1,290 total
includes taxes & fees
12 Jan - 13 Jan
Gold Coast Living: Modern Studio Unit

Apartment in Downtown Chicago

1BR Modern Luxe Apt with In-Unit Laundry
10.0 out of 10, Exceptional, (1 review)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is HK$491
HK$1,313 total
includes taxes & fees
12 Jan - 13 Jan
1BR Modern Luxe Apt with In-Unit Laundry

Apartment in Downtown Chicago

West Loop Living – Bright 1BR
10.0 out of 10, Exceptional, (6 reviews)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
The price is HK$491
HK$1,313 total
includes taxes & fees
12 Jan - 13 Jan
West Loop Living – Bright 1BR
9.6 out of 10, Exceptional, (20 reviews)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
The price is HK$538
HK$1,485 total
includes taxes & fees
14 Jan - 15 Jan
Twice as Nice: Chic 2BR Stay with Style & Space

Apartment in Downtown Chicago

Modern Comfort: 1BR Unit w/ Laundry
9.8 out of 10, Exceptional, (11 reviews)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is HK$491
HK$1,313 total
includes taxes & fees
12 Jan - 13 Jan
Modern Comfort: 1BR Unit w/ Laundry

Apartment in Downtown Chicago

Sun-Drenched 1BR Apartment
10.0 out of 10, Exceptional, (2 reviews)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is HK$491
HK$1,313 total
includes taxes & fees
19 Jan - 20 Jan
Sun-Drenched 1BR Apartment
9.6 out of 10, Exceptional, (4 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
The price is HK$779
HK$2,439 total
includes taxes & fees
13 Jan - 14 Jan
River North Rooftop With In and Out Parking 3

Apartment in Downtown Chicago

The One: A 1BR Stay That Feels Like Home
8.4 out of 10, Very good, (5 reviews)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
The One: A 1BR Stay That Feels Like Home
2.0 star property
The price is HK$491
HK$1,313 total
includes taxes & fees
13 Jan - 14 Jan
Chicago-Themed 1BR in a Central Spot near Downtown

Aparthotel in Downtown Chicago

Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (182 reviews)
"Awesome stay "
United States
Sally
Kasa River North Chicago

Aparthotel in Downtown Chicago

Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (410 reviews)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town

Apartment in Downtown Chicago

Sleek 1BR Apt w/ Laundry
10.0 out of 10, Exceptional, (1 review)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveller
The price is HK$491
HK$1,313 total
includes taxes & fees
21 Jan - 22 Jan
Sleek 1BR Apt w/ Laundry

Apartment in Downtown Chicago

Complete 1BR Home Sum
The price is HK$491
HK$1,313 total
includes taxes & fees
12 Jan - 13 Jan
Complete 1BR Home Sum
2.0 star property
The price is HK$538
HK$1,485 total
includes taxes & fees
19 Jan - 20 Jan
Stylish Japanese-Themed 2BR Apt Close to Downtown
10.0 out of 10, Exceptional, (49 reviews)
"Clean and quiet, perfect for nights to rest after exploring the city"
United States
Joe T.
The price is HK$636
HK$2,154 total
includes taxes & fees
2 Feb - 3 Feb
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
9.4 out of 10, Exceptional, (10 reviews)
"Great place to stay that was close to downtown"
United States
Michelle B.
The price is HK$452
HK$2,587 total
includes taxes & fees
21 Jan - 22 Jan
Spacious 3-bedroom apartment near downtown, FREE PARKING
9.0 out of 10, Wonderful, (19 reviews)
"Had a great stay! Perfect for our needs. Great location. It was an easy walk to the lake and lots of great restaurants nearby!"
United States
Rodney S.
The price is HK$421
HK$1,867 total
includes taxes & fees
12 Jan - 13 Jan
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
2.0 star property
10.0 out of 10, Exceptional, (4 reviews)
"Amazing stay! So comfortable, clean, and the sushi underneath was the icing on the cake! We will definitely stay again when we come back! "
United States
Emily s.
The price is HK$575
HK$1,539 total
includes taxes & fees
13 Jan - 14 Jan
Pine Beam Sloth Apartment next 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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winnetka Hotel Reviews

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 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 are some of the best holiday rentals that Winnetka has to offer?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: This holiday home rental outside of Winnetka offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

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.