Search Holiday Rentals in Winnetka

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12 Dec - 14 Dec
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Top Holiday Rentals in Winnetka

Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (995)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is 2.657.406 ₫
3.893.415 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Sentral Michigan Avenue
Business Apartment, City View | Private kitchen | Fridge, microwave, oven, stovetop
4BR Corporate Suite Central and Modern

4BR Corporate Suite Central and Modern

2.0 star property
Near North Side
10.0 out of 10, Exceptional, (8)
"We loved at our stay at this property. It was one of the best stays we have had on vacation."
United States
Javeria
The price is 26.107.290 ₫
36.188.635 ₫ total
includes taxes & fees
30 Nov - 1 Dec
4BR Corporate Suite Central and Modern
Front of property – evening/night
Level Chicago – Old Town

Level Chicago – Old Town

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (388)
"Property was clean, centrally located with wonderful staff. Will definitely stay again."
United States
Michelle
Level Chicago – Old Town
Free WiFi, bed sheets
Chicago luxury home suites

Chicago luxury home suites

2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job."
Canada
pouya
The price is 4.746.780 ₫
5.572.246 ₫ total
includes taxes & fees
27 Nov - 28 Nov
Chicago luxury home suites
Business centre
Kasa River North Chicago

Kasa River North Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (180)
"Awesome stay "
United States
Sally
Kasa River North 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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Top Winnetka Hotel Reviews

Hilton Chicago

Hilton Chicago

10/10 Excellent
"great cusomter service"
Ibrahim 3-night trip
Posted 20 hours ago
Hilton Chicago

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 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.