A serene lake with reflections of trees and a cloudy sky.

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Crestwood holiday rentals

A modern building with the name 'SENIORAL' prominently displayed on the facade.

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,387 reviews)
"Perfect location to stay at if attending the bears games !"
United States
Jacob
The price is ₹13,579
₹15,941 total
includes taxes & fees
9 Nov - 10 Nov
Sentral Michigan Avenue
A modern kitchen with a large island, bar stools, and a city view.

2. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (545 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
The price is ₹26,448
₹33,378 total
includes taxes & fees
8 Nov - 9 Nov
Level Chicago – Old Town
Lake

3. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (73 reviews)
"First time staying there and we absolutely loved our stay. We will definitely be going back."
United States
Iliana
The price is ₹14,204
₹21,611 total
includes taxes & fees
10 Nov - 11 Nov
Kasa Lake Shore Chicago
A large, two-story house with a prominent gable roof, a front porch, and a well-maintained lawn.

4. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (14 reviews)
"Great location with parking included"
United States
Melissa
At Home in Oak Park
A spacious living room with a grand piano, a comfortable sofa, and a dining area with a chandelier.

5. Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
8.8 out of 10, Excellent, (6 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is ₹16,983
₹29,972 total
includes taxes & fees
27 Oct - 28 Oct
Historic Oak Park Home
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

6. Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
3.0 star property
Forest Park
The price is ₹22,948
₹45,026 total
includes taxes & fees
27 Oct - 28 Oct
Classic Forest Park Foursquare < 1 Mi to Blue Line
A modern building with large glass windows, surrounded by a grassy area with trees and a pathway.

7. The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.4 out of 10, Exceptional, (8 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is ₹16,821
₹29,787 total
includes taxes & fees
27 Oct - 28 Oct
The Oak Park Loft
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 Crestwood Hotel Reviews

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

10/10 Excellent
"Great hotel in a great location, perfect starting point for walking nearly everywhere we wanted to go. Staff were friendly and helpful when we checked in. Rooms were large and clean."
Marshall 3-night trip
Posted less than an hour ago
Sports Illustrated Resorts Chicago

Find out more about Crestwood

Holiday Rentals in Crestwood

Search for holiday rentals in Crestwood on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Crestwood using one of the methods below:

  • View our selection of featured holiday rentals in Crestwood
  • Use the map to find apartments and other holiday homes in the Crestwood neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Crestwood while they last

Look no further and take a look at our great range of rental properties in Crestwood!

Frequently asked questions

Can I find a holiday rental in Crestwood?

Yes, there are holiday rentals in Crestwood close to Hollywood Park, or you can select a more secluded option if you're looking for a relaxing stay. The shops and restaurants are several reasons why visitors like Crestwood. Make sure you have time to check out the entertainment choices while you're in the area.

How many holiday rentals are there in Crestwood?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Crestwood stay.

What can I see and do in Crestwood?

While exploring the area, visit family-friendly sights like Hollywood Park, or get outside and enjoy nature at Marquette Park. In the wider area, you’ll find Soldier Field and Gaelic Park.

What are holiday rentals like in Crestwood?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Crestwood. Holiday rentals offer extras such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for a family getaway.