Crestwood Holiday Rentals

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Our top choices for Crestwood holiday rentals

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,081 reviews)
"Best full kitchen multi-room family lodging"
United States
Lee
The price is S$200
includes taxes & fees
22 Feb - 23 Feb
Sentral Michigan Avenue

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (427 reviews)
"Clean, nice amenities and great staff."
United States
Sydnee
Level Chicago – Old Town

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (183 reviews)
"Awesome stay "
United States
Sally
Kasa River North Chicago

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 S$324
includes taxes & fees
17 Feb - 18 Feb
The Oak Park Loft

Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"Wanted a house in oak park and this was such a pleasant, comfortable and convenient place. Really comfortable beds too. Even a lovely piano. "
United States
judith
The price is S$340
includes taxes & fees
3 Mar - 4 Mar
Historic Oak Park Home

Chicago Third Floor Studio by 747 Lofts

Chicago Third Floor Studio by 747 Lofts
2.0 star property
West Town
9.8 out of 10, Exceptional, (7 reviews)
"Clean, easy to check in, all the household items you’d expect"
United States
Jason
Chicago Third Floor Studio by 747 Lofts

Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Comfort Inn Chicago Southland I-80 & I-294 Near Casino
3.0 star property
Harvey
4.2 out of 10, (72 reviews)
"Under renovations so some rooms have missing appliances, even through an app they require a deposit. Utter wise nice room and workers"
United States
Destin
The price is S$121
includes taxes & fees
17 Feb - 18 Feb
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.4 out of 10, Exceptional, (9 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is S$332
includes taxes & fees
3 Mar - 4 Mar
At Home in Oak Park

Historic Oak Park Residence

Historic Oak Park Residence
2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"Absolutely awesome "
United States
Erik
The price is S$355
includes taxes & fees
3 Mar - 4 Mar
Historic Oak Park Residence
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 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 Lake Katherine Nature Center. 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.