Winnetka Holiday Rentals

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Holiday Rentals in Winnetka

2 Connecting Suites at a 4⭐️ Hotel

The price is NZ$1,239
includes taxes & fees
18 Aug - 19 Aug
2 Connecting Suites at a 4⭐️ Hotel

Smart Simple and Spacious 4BR Apt State 203

Smart Simple and Spacious 4BR Apt State 203

2 Connecting Suites at a 5⭐️ Hotel

The price is NZ$6,072
includes taxes & fees
10 Aug - 11 Aug
2 Connecting Suites at a 5⭐️ Hotel

Luxury Unit with Rooftop Lounge & Spectacular City Views

The price is NZ$382
includes taxes & fees
27 July - 28 July
Luxury Unit with Rooftop Lounge & Spectacular City Views

Cozy Room with Rooftop Lounge & City Views in River North

The price is NZ$437
includes taxes & fees
27 July - 28 July
Cozy Room with Rooftop Lounge & City Views in River North

Spacious Room with Rooftop Lounge & Scenic Views of Chicago

The price is NZ$457
includes taxes & fees
27 July - 28 July
Spacious Room with Rooftop Lounge & Scenic Views of Chicago

Modern Suite with Rooftop Lounge & Views of Downtown Chicago

The price is NZ$551
includes taxes & fees
24 July - 25 July
Modern Suite with Rooftop Lounge & Views of Downtown Chicago

2 Spacious King Room with Rooftop Lounge & Scenic Views of Chicago

The price is NZ$775
includes taxes & fees
27 July - 28 July
2 Spacious King Room with Rooftop Lounge & Scenic Views of Chicago

2 Relaxing Rooms with Rooftop Lounge & City Views of Chicago

The price is NZ$891
includes taxes & fees
27 July - 28 July
2 Relaxing Rooms with Rooftop Lounge & City Views of Chicago

2 Suites with Rooftop Lounge & Beautiful Views of Chicago Skyline

The price is NZ$928
includes taxes & fees
27 July - 28 July
2 Suites with Rooftop Lounge & Beautiful Views of Chicago Skyline

2 Luxury Queen with Rooftop Lounge & City Views Near Attractions

The price is NZ$1,045
includes taxes & fees
27 July - 28 July
2 Luxury Queen with Rooftop Lounge & City Views Near Attractions

Walk to the Beach! Theater-Coffee Bar-Games-Gym

2.0 star property
9.6 out of 10, Exceptional, (8)
"Everything was as it was described. Very nice "
The price is NZ$1,306
includes taxes & fees
5 Aug - 6 Aug
Walk to the Beach! Theater-Coffee Bar-Games-Gym

Family Friendly 2 Bedroom Full Kitchen Free Laundry Work Space 1 FREE Parking

The price is NZ$928
includes taxes & fees
23 July - 24 July
Family Friendly 2 Bedroom Full Kitchen Free Laundry Work Space 1 FREE Parking

Stylish 1BR in West Loop

The price is NZ$392
includes taxes & fees
24 July - 25 July
Stylish 1BR in West Loop

Sun-Drenched 1BR Apartment

The price is NZ$487
includes taxes & fees
18 Aug - 19 Aug
Sun-Drenched 1BR Apartment

The One: A 1BR Stay That Feels Like Home

8.0 out of 10, Very good, (1)
"The apartment looked exactly like the pictures and was very well kept. Everything was clean and functional and we didn’t have any issues. The neighborhood is very quiet and safe and also has a target nearby for quick grocery trips. Connectivity wise, there’s a busy stop within walking distance but no train stations.The host was also very responsive and helpful. We didn’t have any trouble checking in or checking out.Overall a great experience and comfortable stay."
The price is NZ$359
includes taxes & fees
24 July - 25 July
The One: A 1BR Stay That Feels Like Home

Simple, Comfy Living - Furnished 1BR Pad

Simple, Comfy Living - Furnished 1BR Pad

Bright & Modern Lakeview Studio

8.0 out of 10, Very good, (1)
"This is a great location to hit the Lakeview neighborhood with Wrigley Field just a couple blocks over. When trying to get the check-in instructions, there were a lot of hoops to jump through to get the payment to the management company for this property. I had to contact the host (management company) multiple times to get the links to the forms to upload a driver's license and selfie holding said driver's license. Another URL to get to the payment Venmo account. And another URL for the...
The price is NZ$344
includes taxes & fees
24 July - 25 July
Bright & Modern Lakeview Studio

Paradise 1BR Apt in Lincoln Park

Paradise 1BR Apt in Lincoln Park

Modern & Fully Furnished 1BR Apt

The price is NZ$318
includes taxes & fees
24 July - 25 July
Modern & Fully Furnished 1BR Apt
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

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?

4BR Retreat w/ Theater, Game Room & Backyard: This holiday home rental outside of Winnetka offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Winnetka?

Choose from 3 Expedia holiday rentals in Winnetka for a memorable holiday.

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 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.