Crestwood Vacation Rentals

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Check prices for these dates

Tonight
Jan 7 - Jan 8
Tomorrow
Jan 8 - Jan 9
This weekend
Jan 9 - Jan 11
Next weekend
Jan 16 - Jan 18

Our top choices for Crestwood vacation rentals

Indoor pool
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1036)
"Place was very nice and clean. We enjoyed the stay there. Will book it again when we come back to Chicago visit again. "
United States
Khalid
The price is P6,863
P9,791 total
includes taxes & fees
Jan 11 - Jan 12
Sentral Michigan Avenue
Lounge
Kasa River North Chicago

Aparthotel in Downtown Chicago

Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (182)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Full-size fridge, microwave, oven, stovetop
Level Chicago – Old Town

Aparthotel in Downtown Chicago

Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (408)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town
Exterior
Chicago luxury home suites

Aparthotel in Downtown Chicago

Chicago luxury home suites
2.0 star property
10.0 out of 10, Exceptional, (4)
"Amazing stay! The location is very central and close to everything. The room was spotless, and the mattress was very comfortable. I really appreciated that the property is pet friendly. I was able to bring my dog along, which made the trip even better. The view was absolutely stunning. The hosts were very responsive and helpful throughout our stay. Highly recommend!"
Canada
Alex
The price is P5,861
P6,881 total
includes taxes & fees
Jan 8 - Jan 9
Chicago luxury home suites
Interior
River West, Third Floor Chicago by 747 Lofts

Aparthotel in West Town

River West, Third Floor Chicago by 747 Lofts
2.0 star property
9.0 out of 10, Wonderful, (17)
"Loved the space and location "
United States
Caroline
The price is P4,462
P20,523 total
includes taxes & fees
Jan 25 - Jan 26
River West, Third Floor Chicago by 747 Lofts
Desk, laptop workspace, blackout drapes, free WiFi
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Aparthotel in Harvey

Comfort Inn Chicago Southland I-80 & I-294 Near Casino
3.0 star property
4.0 out of 10, (69)
"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 P5,000
P5,649 total
includes taxes & fees
Jan 10 - Jan 11
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Interior
Classic Forest Park Foursquare < 1 Mi to Blue Line

Cottage in Forest Park

Classic Forest Park Foursquare < 1 Mi to Blue Line
3.0 star property
The price is P9,339
P24,381 total
includes taxes & fees
Jan 8 - Jan 9
Classic Forest Park Foursquare < 1 Mi to Blue Line
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

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"Excellent rooms! Very roomy! Wonderful location. Will stay here again. "
Jasmine 4-night trip
Posted 6 hours ago
Hilton Chicago/Magnificent Mile Suites

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 vacation rental in Crestwood?

Yes, there are vacation rentals in Crestwood close to Hollywood Park, or you can go with a more remote 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 vacation rentals are there in Crestwood?

With 3 Expedia vacation rentals, you're sure 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 larger area, you’ll find Soldier Field and Trinity Christian College.

What are vacation rentals like in Crestwood?

Vacation rentals are private accommodations you can reserve for a few days or a quick weekend in Crestwood. Vacation rentals offer amenities like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for a family trip or a small group gathering.