Winnetka Holiday Rentals

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Holiday Rentals in Winnetka

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (822)
"Great stay!"
The price is AU$392
includes taxes & fees
4 Aug - 5 Aug
Sentral Michigan Avenue

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.4 out of 10, Very good, (323)
"Super cool spot in a great part of the city."
The price is AU$334
includes taxes & fees
10 Aug - 11 Aug
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (326)
"Hotel was nice"
The price is AU$837
includes taxes & fees
30 July - 31 July
Level Chicago – Old Town

Kasa Magnificent Mile Chicago

4.0 star property
9.4 out of 10, Exceptional, (443)
"Nice views and convenient location to transit and dining"
Kasa Magnificent Mile Chicago

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (566)
"Great place and location. "
The price is AU$393
includes taxes & fees
24 July - 25 July
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (318)
"Great stay"
Kasa South Loop Chicago

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (195)
"Fantastically located snd brilliantly appointed aparthotel. Absolutely perfect for our stay, where we were competing at the HYROX world championships. The room was super spacious and had all amenities you could wish for. "
The price is AU$410
includes taxes & fees
10 Aug - 11 Aug
Sonder by Marriott Bonvoy The Burnham Apartments Loop

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
8.0 out of 10, Very good, (117)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is AU$235
includes taxes & fees
4 Aug - 5 Aug
Sonder by Marriott Bonvoy The Plymouth Apartments Loop

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (72)
"Good people great breakfast "
The price is AU$369
includes taxes & fees
16 July - 17 July
The Gem Museum Suites

The Neighborhood Hotel-Little Italy

4.0 star property
9.8 out of 10, Exceptional, (173)
"Great spot. "
The Neighborhood Hotel-Little Italy

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very good, (167)
"Great location and much larger space than I expected. Great location in the Loop with access to public transit and walkable. "
The price is AU$302
includes taxes & fees
10 Aug - 11 Aug
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (155)
"Great location and very clean! Will definitely be staying again. "
Kasa River North Chicago

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.6 out of 10, Excellent, (42)
"Our stay was amazing. "
The price is AU$355
includes taxes & fees
27 July - 28 July
Sonder by Marriott Bonvoy The Opal Apartments River North

Wrigleyville Suites

2.0 star property
9.2 out of 10, Wonderful, (7)
"Absolutely loved staying here! Would 10/10 recommend this place!"
The price is AU$228
includes taxes & fees
16 July - 17 July
Wrigleyville Suites

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
9.0 out of 10, Wonderful, (55)
"Great location, easy stay!"
The price is AU$393
includes taxes & fees
10 Aug - 11 Aug
Sonder by Marriott Bonvoy Greektown Apartments

Huge Projector and Designated Workspace - Near Wrigley!

Huge Projector and Designated Workspace - Near Wrigley!

Lakeview 2BR Apartment

10.0 out of 10, Exceptional, (1)
"Great location, charming building. The photos in the listing are very accurate. Super close to the L and restaurants."
The price is AU$326
includes taxes & fees
28 July - 29 July
Lakeview 2BR Apartment

Clean & Equipped 1BR Apt

10.0 out of 10, Exceptional, (1)
"Was very clean and comfortable simply furnished but nice close to the things we were looking for. "
The price is AU$288
includes taxes & fees
20 July - 21 July
Clean & Equipped 1BR Apt

Cozy, Fully Set-Up 1BR Space

10.0 out of 10, Exceptional, (2)
"Great communication, location, and would love to stay here again "
The price is AU$288
includes taxes & fees
16 July - 17 July
Cozy, Fully Set-Up 1BR Space

Luxurious 3 Bedroom Apartment in Chicago

9.6 out of 10, Exceptional, (12)
"Great property! Would visit again!"
Luxurious 3 Bedroom Apartment in 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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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.