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

Crestwood Vacation Rentals

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

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, (1,203 reviews)
"Great location"
United States
JAVIER
The price is RM619
RM847 total
includes taxes & fees
6 Jul - 7 Jul
Sentral Michigan Avenue
Dining room

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (814 reviews)
"Great place to stay."
United States
Benedictine
The price is RM835
RM1,220 total
includes taxes & fees
6 Jul - 7 Jul
Kasa Magnificent Mile Chicago
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, (497 reviews)
"Very clean and loved the location and amenities with the store on the first floor was fantastic"
United States
Kimberly
The price is RM1,169
RM1,473 total
includes taxes & fees
6 Jul - 7 Jul
Level Chicago – Old Town
Living area

Ground Floor Studios in Chicago by 747 Lofts

Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
West Town
8.6 out of 10, Excellent, (23 reviews)
"Great area and surprisingly nice room!"
United States
Michael
The price is RM367
RM584 total
includes taxes & fees
8 Jul - 9 Jul
Ground Floor Studios in Chicago by 747 Lofts
Exterior

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (6 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is RM656
RM1,203 total
includes taxes & fees
27 Jul - 28 Jul
The Oak Park Loft
Lounge

Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is RM857
RM1,433 total
includes taxes & fees
28 Jul - 29 Jul
Historic Oak Park Home
Individually decorated, individually furnished, iron/ironing board

Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
The price is RM1,059
RM1,500 total
includes taxes & fees
6 Jul - 7 Jul
Kasa Lake Shore Chicago
Interior

Cabin 105 by 747 Lofts

Cabin 105 by 747 Lofts
2.0 star property
West Town
6.0 out of 10, (2 reviews)
"The code that was provided was incorrect. I was so anxious waiting outside the building until I was lucky that other guests were out and helped me get in. I tried reaching the “24/7” line but no response until a while and they had to reset everything before I was able to get in. First and last time I will be staying here. The bed is so small for even one person and the bathroom lights felt like a ghost was there. Do not book here, your anxiety will be through the roof !"
United States
Jamila
The price is RM957
RM1,204 total
includes taxes & fees
24 Jul - 25 Jul
Cabin 105 by 747 Lofts
Interior

River West, Third Floor Chicago by 747 Lofts

River West, Third Floor Chicago by 747 Lofts
2.0 star property
West Town
9.0 out of 10, Wonderful, (18 reviews)
"Loved the space and location "
United States
Caroline
The price is RM615
RM845 total
includes taxes & fees
13 Jul - 14 Jul
River West, Third Floor Chicago by 747 Lofts
Lounge

At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (11 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is RM883
RM1,462 total
includes taxes & fees
22 Jul - 23 Jul
At Home in Oak Park
Exterior

Historic Oak Park Residence

Historic Oak Park Residence
2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"The house is in an amazing neighborhood, easy access to subway, extremely clean and great follow-up and follow through communication with owner!"
United States
Ann-Marie
The price is RM1,118
RM1,732 total
includes taxes & fees
27 Jul - 28 Jul
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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Top Crestwood Hotel Reviews

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

8/10 Good
"I was very impressed with Whitehall hotel there’s nothing I would change about it. My visit was a wonderful visit. Thank you Expedia."
Eleanor 2-night trip
Posted less than an hour ago
The Whitehall Hotel, BW Premier Collection

Find out more about 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 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.