Winnetka Holiday Rentals

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Holiday Rentals in Winnetka

All Set Up - Furnished 1BR Unit

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 AU$317
includes taxes & fees
17 July - 18 July
All Set Up - Furnished 1BR Unit

Sun-Drenched 1BR Apartment

The price is AU$399
includes taxes & fees
17 July - 18 July
Sun-Drenched 1BR Apartment

Cozy studio in Andersonville Chicago

9.2 out of 10, Wonderful, (10)
"I thought I was in a $300 night hotel, private, and serene surrounding"
The price is AU$225
includes taxes & fees
15 July - 16 July
Cozy studio in Andersonville Chicago

Stylish 1BR in West Loop

The price is AU$308
includes taxes & fees
16 July - 17 July
Stylish 1BR in West Loop

A quiet stay while you are away

9.8 out of 10, Exceptional, (32)
"We stayed a few nights and everything was nice and clean. Thank you!"
A quiet stay while you are away

Luxury Unit with Rooftop Lounge & Spectacular City Views

The price is AU$335
includes taxes & fees
27 July - 28 July
Luxury Unit with Rooftop Lounge & Spectacular City Views

Prime City Stay in a 1BR Apt

9.0 out of 10, Wonderful, (2)
"Location is very good, 10 mins walk to irving blue line station, and the apartment has lot of light during the day as it was a corner unit."
The price is AU$277
includes taxes & fees
16 July - 17 July
Prime City Stay in a 1BR Apt

Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG

2.0 star property
9.6 out of 10, Exceptional, (9)
"Lovely little cottage in great location with excellent restaurants close by. Had everything we needed for our stay. Kitchen was perfectly equipped and having the washer dryer was such a bonus. The communication with the landlord was very good. Would absolutely stay here again. "
The price is AU$416
includes taxes & fees
15 July - 16 July
Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG

Light-Filled 1-Bedroom Apt

10.0 out of 10, Exceptional, (1)
The price is AU$281
includes taxes & fees
15 July - 16 July
Light-Filled 1-Bedroom Apt

2 Connecting Suites at a 4⭐️ Hotel

The price is AU$1,213
includes taxes & fees
11 Aug - 12 Aug
2 Connecting Suites at a 4⭐️ Hotel

Master qtr close to nature & easy urban facilities

9.8 out of 10, Exceptional, (57)
"Great spot."
The price is AU$310
includes taxes & fees
24 July - 25 July
Master qtr close to nature & easy urban facilities

Quaint Bungalow, near Great Lakes Naval Base

10.0 out of 10, Exceptional, (61)
"Great experience, lots of cooking materials "
The price is AU$472
includes taxes & fees
20 July - 21 July
Quaint Bungalow, near Great Lakes Naval Base

1BR Chic & Sunny Place

10.0 out of 10, Exceptional, (1)
"Location was perfect for visiting family and getting around the city. Bed was extra comfy and the AC worked wonderfully. Will stay here again on our next visit. "
The price is AU$279
includes taxes & fees
16 July - 17 July
1BR Chic & Sunny Place

Chic hotel with WiFi, fitness room, AC in lovely Schaumburg

The price is AU$218
includes taxes & fees
15 July - 16 July
Chic hotel with WiFi, fitness room, AC in lovely Schaumburg

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 AU$291
includes taxes & fees
16 July - 17 July
Bright & Modern Lakeview Studio

2 Connecting Suites at a 5⭐️ Hotel

The price is AU$5,562
includes taxes & fees
10 Aug - 11 Aug
2 Connecting Suites at a 5⭐️ Hotel

Peaceful 1BR Escape in Evanston

10.0 out of 10, Exceptional, (2)
"Great for a quick trip to Chicago. Walkable to lakefront beach, restaurants, grocery stores, coffee chops. Less than a block to the train for downtown Chicago. Beautiful apartment, very spacious. Kitchen has everything you need to cook meals, make coffee, etc. Relaxing atmosphere, charming neighborhood. "
The price is AU$274
includes taxes & fees
20 July - 21 July
Peaceful 1BR Escape in Evanston

Vintage Urban Retreat

10.0 out of 10, Exceptional, (8)
"Great house,great location,close to a lot of attractions and bars. Owners was egged to help and responded quickly to all our questions "
The price is AU$692
includes taxes & fees
15 July - 16 July
Vintage Urban Retreat

2BR Traveler's Favorite, Modern and Clean

The price is AU$555
includes taxes & fees
5 Aug - 6 Aug
2BR Traveler's Favorite, Modern and Clean

Sleek Style 3BR Haven - Free Parking - Ashland 2N

8.0 out of 10, Very good, (1)
"Centrally located "
The price is AU$356
includes taxes & fees
15 July - 16 July
Sleek Style 3BR Haven - Free Parking - Ashland 2N
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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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.