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Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

Our top choices for Crestwood holiday rentals

Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,115 reviews)
"Clean room and nice for a family of 4. The rooms could use some touch ups (paint, shower grout) and the pool could use a clean (clearly coming out of winter but still nice). "
United States
Marki
The price is ฿3,888
฿5,529 total
includes taxes & fees
1 Apr - 2 Apr
Sentral Michigan Avenue
Full-sized fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (453 reviews)
"Staff was really nice"
United States
Anita
The price is ฿6,361
฿8,278 total
includes taxes & fees
30 Mar - 31 Mar
Level Chicago – Old Town
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (187 reviews)
"Nice area if you are renting a car, be aware that you would have to pay for street parking or go over a few blocks and park in a parking lot."
United States
Daysha
The price is ฿4,383
฿7,848 total
includes taxes & fees
8 Apr - 9 Apr
Kasa River North Chicago
Design Apartment, Private Bathroom (The Oak Park Loft) | Exterior

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is ฿3,971
฿8,200 total
includes taxes & fees
30 Mar - 31 Mar
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

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4/10 Poor
"Breakfast was bland, cups, plates, forks not clean. Housekeeping didn’t clean rooms property, wasn’t made aware roof top wasn’t open if that was the case I would have never booked. Staff poorly communicated late checkout guidelines. "
Preiajah Elisa 2-night trip
Posted 1 hour ago
Hotel Riu Plaza Chicago

Find out more about Crestwood

Search for holiday rentals in Crestwood on Expedia! 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 Centennial Park. In the wider area, you’ll find Soldier Field and Trinity Christian College.

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.