Crestwood Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Nov 21 - Nov 22
Tomorrow
Nov 22 - Nov 23
This weekend
Nov 21 - Nov 23
Next weekend
Nov 28 - Nov 30

Vacation Rentals in Crestwood

Indoor pool
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

4.0 star property
9.2 out of 10, Wonderful, (987)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is P5,938
P8,700 total
includes taxes & fees
Dec 18 - Dec 19
Sentral Michigan Avenue
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago

Aparthotel in Downtown Chicago

4.0 star property
9.2 out of 10, Wonderful, (625)
"Room was very nice, location was wonderful."
United States
Nicholas
Kasa Magnificent Mile Chicago
Front of property - evening/night
Level Chicago – Old Town

Aparthotel in Downtown Chicago

4.0 star property
9.0 out of 10, Wonderful, (384)
"Property was clean, centrally located with wonderful staff. Will definitely stay again."
United States
Michelle
Level Chicago – Old Town
Balcony
Kasa South Loop Chicago

Aparthotel in Downtown Chicago

4.0 star property
9.4 out of 10, Exceptional, (376)
"An excellent place to stay in Chicago downtown."
United States
ABDULHAFEEZ
Kasa South Loop Chicago
Front of property
The Neighborhood Hotel-Little Italy

Aparthotel in Near West Side

4.0 star property
9.6 out of 10, Exceptional, (219)
"Staff was courteous. Great location."
United States
Pamela
The Neighborhood Hotel-Little Italy
Business center
Kasa River North Chicago

Aparthotel in Downtown Chicago

4.0 star property
9.4 out of 10, Exceptional, (179)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Free WiFi, bed sheets
Chicago luxury home suites

Aparthotel in Downtown Chicago

2.0 star property
10.0 out of 10, Exceptional, (1)
"This was Amazing stay I have ever had in my life. Wonderful host, super clean. Stunning views, close to everything that you would needed. "
New Zealand
Moha
The price is P17,679
P20,753 total
includes taxes & fees
Nov 23 - Nov 24
Chicago luxury home suites
Desk, laptop workspace, blackout drapes, free WiFi
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Aparthotel in Harvey

3.0 star property
3.8 out of 10, (67)
"Good "
United States
Abel
The price is P4,283
P4,839 total
includes taxes & fees
Nov 23 - Nov 24
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Private kitchen
Stylish Apartment near Chicago Downtown

Aparthotel in Bridgeport

2.0 star property
The price is P14,673
P23,313 total
includes taxes & fees
Dec 8 - Dec 9
Stylish Apartment near Chicago Downtown
Interior
Art Villa

Aparthotel in West Town

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
United States
tomonobu
The price is P22,234
P47,289 total
includes taxes & fees
Nov 24 - Nov 25
Art Villa
Exterior
Ground Floor Studios in Chicago by 747 Lofts

Aparthotel in West Town

2.0 star property
9.0 out of 10, Wonderful, (21)
"The stay lacked in shelf space as well as other amenities that could be useful. "
United States
Zugeily
The price is P3,373
P7,740 total
includes taxes & fees
Nov 30 - Dec 1
Ground Floor Studios in Chicago by 747 Lofts
Private kitchen
River West, Third Floor Chicago by 747 Lofts

Aparthotel in West Town

2.0 star property
9.0 out of 10, Wonderful, (17)
"Overall solid property, I will return."
United States
Fletcher
The price is P3,790
P8,297 total
includes taxes & fees
Nov 30 - Dec 1
River West, Third Floor Chicago by 747 Lofts
Living area
Stylish 1BR in West Loop - Lake 301 rep

Apartment in Downtown Chicago

4.0 star property
Stylish 1BR in West Loop - Lake 301 rep
Interior
Historic Oak Park Home

Apartment in Oak Park

2.0 star property
10.0 out of 10, Exceptional, (5)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
Historic Oak Park Home
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Crestwood Hotel Reviews

citizenM Chicago Downtown

citizenM Chicago Downtown

10/10 Excellent
"Yed"
Desiree 2-night trip
Posted 4 hours ago
citizenM Chicago Downtown

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 Centennial Park. 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.