Winnetka Holiday Rentals

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Check prices for these dates

Tonight
8 Jul - 9 Jul
Tomorrow
9 Jul - 10 Jul
This weekend
11 Jul - 13 Jul
Next weekend
18 Jul - 20 Jul

Holiday Rentals in Winnetka

2 Connecting Suites at a 4⭐️ Hotel
Beach

2 Connecting Suites at a 4⭐️ Hotel

The price is HK$4,438
HK$5,919 total
includes taxes & fees
4 Aug - 5 Aug
2 Connecting Suites at a 4⭐️ Hotel
Smart Simple and Spacious 4BR Apt State 203
Fridge, microwave, oven, stovetop

Smart Simple and Spacious 4BR Apt State 203

The price is HK$1,405
HK$3,430 total
includes taxes & fees
21 Jul - 22 Jul
Smart Simple and Spacious 4BR Apt State 203
2 Connecting Suites at a 5⭐️ Hotel
Exterior

2 Connecting Suites at a 5⭐️ Hotel

The price is HK$21,362
HK$28,449 total
includes taxes & fees
13 Jul - 14 Jul
2 Connecting Suites at a 5⭐️ Hotel
Luxury Unit with Rooftop Lounge & Spectacular City Views
Exterior

Luxury Unit with Rooftop Lounge & Spectacular City Views

The price is HK$1,083
HK$1,631 total
includes taxes & fees
9 Jul - 10 Jul
Luxury Unit with Rooftop Lounge & Spectacular City Views
Spacious Room with Rooftop Lounge & Scenic Views of Chicago
Exterior

Spacious Room with Rooftop Lounge & Scenic Views of Chicago

The price is HK$1,358
HK$1,954 total
includes taxes & fees
9 Jul - 10 Jul
Spacious Room with Rooftop Lounge & Scenic Views of Chicago
Cozy Room with Rooftop Lounge & City Views in River North
Exterior

Cozy Room with Rooftop Lounge & City Views in River North

The price is HK$1,287
HK$1,871 total
includes taxes & fees
9 Jul - 10 Jul
Cozy Room with Rooftop Lounge & City Views in River North
Modern Suite with Rooftop Lounge & Views of Downtown Chicago
Exterior

Modern Suite with Rooftop Lounge & Views of Downtown Chicago

The price is HK$1,562
HK$2,193 total
includes taxes & fees
9 Jul - 10 Jul
Modern Suite with Rooftop Lounge & Views of Downtown Chicago
2 Spacious King Room with Rooftop Lounge & Scenic Views of Chicago
Exterior

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

The price is HK$2,167
HK$3,201 total
includes taxes & fees
9 Jul - 10 Jul
2 Spacious King Room with Rooftop Lounge & Scenic Views of Chicago
2 Relaxing Rooms with Rooftop Lounge & City Views of Chicago
Exterior

2 Relaxing Rooms with Rooftop Lounge & City Views of Chicago

The price is HK$2,575
HK$3,803 total
includes taxes & fees
9 Jul - 10 Jul
2 Relaxing Rooms with Rooftop Lounge & City Views of Chicago
2 Suites with Rooftop Lounge & Beautiful Views of Chicago Skyline
Exterior

2 Suites with Rooftop Lounge & Beautiful Views of Chicago Skyline

The price is HK$2,708
HK$3,977 total
includes taxes & fees
9 Jul - 10 Jul
2 Suites with Rooftop Lounge & Beautiful Views of Chicago Skyline
2 Luxury Queen with Rooftop Lounge & City Views Near Attractions
Exterior

2 Luxury Queen with Rooftop Lounge & City Views Near Attractions

The price is HK$3,116
HK$4,526 total
includes taxes & fees
9 Jul - 10 Jul
2 Luxury Queen with Rooftop Lounge & City Views Near Attractions
Stylish 1BR in West Loop
Fridge, microwave, oven, stovetop

Stylish 1BR in West Loop

The price is HK$848
HK$1,572 total
includes taxes & fees
14 Jul - 15 Jul
Stylish 1BR in West Loop
Sun-Drenched 1BR Apartment
Fridge, microwave, oven, stovetop

Sun-Drenched 1BR Apartment

The price is HK$1,484
HK$2,348 total
includes taxes & fees
5 Aug - 6 Aug
Sun-Drenched 1BR Apartment
All Set Up - Furnished 1BR Unit
1 bedroom, iron/ironing board, travel cot, WiFi

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 HK$848
HK$1,572 total
includes taxes & fees
9 Jul - 10 Jul
All Set Up - Furnished 1BR Unit
Bright & Modern Lakeview Studio
WiFi, bed sheets

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 HK$848
HK$1,494 total
includes taxes & fees
13 Jul - 14 Jul
Bright & Modern Lakeview Studio
Modern & Fully Furnished 1BR Apt
1 bedroom, WiFi, bed sheets

Modern & Fully Furnished 1BR Apt

The price is HK$769
HK$1,494 total
includes taxes & fees
5 Aug - 6 Aug
Modern & Fully Furnished 1BR Apt
Elegant 2BR Apartment w/ In-Unit Laundry
Fridge, microwave, oven, stovetop

Elegant 2BR Apartment w/ In-Unit Laundry

The price is HK$1,036
HK$2,014 total
includes taxes & fees
28 Jul - 29 Jul
Elegant 2BR Apartment w/ In-Unit Laundry
Comfy 2BR in Heart of Lakeview
Interior

Comfy 2BR in Heart of Lakeview

The price is HK$769
HK$1,612 total
includes taxes & fees
9 Jul - 10 Jul
Comfy 2BR in Heart of Lakeview
Spacious 4BR Retreat - Chase E1
Fridge, microwave, oven, dishwasher

Spacious 4BR Retreat - Chase E1

2.0 out of 10, (1)
"3 hours before we were supposed to check-in they canceled. They had my cell phone and didn't contact me. I had messaged them to get check in information and was only told at that time the place was now unavailable. For something as important as cancelling last minute they should have called, messaged and emailed. They had no problem requiring me via my cell phone to give them not only give them the names and ages of every guest staying but a picture of my passport and CC. Was this just a scam to...
The price is HK$918
HK$2,891 total
includes taxes & fees
9 Jul - 10 Jul
Spacious 4BR Retreat - Chase E1
Great Layout – Spacious 2BR Apt
2 bedrooms, iron/ironing board, travel cot, WiFi

Great Layout – Spacious 2BR Apt

The price is HK$722
HK$1,564 total
includes taxes & fees
15 Jul - 16 Jul
Great Layout – Spacious 2BR 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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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?

Riverfront Libertyville Retreat w/ Outdoor Kitchen: This holiday home rental outside of Winnetka offers a balcony, a selection of games and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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.