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
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Crestwood vacation rentals

Exterior

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,327 reviews)
"clean property, amazing staff, in-unit laundry machines, awesome location"
United States
Allison
The price is NT$4,842
NT$6,618 total
includes taxes & fees
Sep 27 - Sep 28
Sentral Michigan Avenue
Lake

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (34 reviews)
"Location is perfect to visit Chicago for the weekend. The unit is clean and size is perfect for the family."
United States
Xiaoyu
The price is NT$27,941
NT$37,760 total
includes taxes & fees
Oct 1 - Oct 2
Kasa Lake Shore Chicago
Full-size fridge, microwave, oven, stovetop

3. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (527 reviews)
"Location and facility was very nice"
United States
Brian
The price is NT$9,344
NT$11,754 total
includes taxes & fees
Sep 28 - Sep 29
Level Chicago – Old Town
Apartment, Private Bathroom | Lounge

4. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is NT$6,381
NT$10,839 total
includes taxes & fees
Oct 6 - Oct 7
At Home in Oak Park
House (3 Bedrooms) | Interior

5. Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
3.0 star property
Forest Park
The price is NT$7,701
NT$15,111 total
includes taxes & fees
Sep 22 - Sep 23
Classic Forest Park Foursquare < 1 Mi to Blue Line
Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Lounge

6. Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
8.8 out of 10, Excellent, (6 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is NT$6,959
NT$11,501 total
includes taxes & fees
Oct 14 - Oct 15
Historic Oak Park Home
Design Apartment, Private Bathroom (The Oak Park Loft) | Exterior

7. The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.2 out of 10, Wonderful, (7 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is NT$5,652
NT$10,004 total
includes taxes & fees
Oct 13 - Oct 14
The Oak Park Loft
Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Exterior

8. 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 NT$8,502
NT$13,267 total
includes taxes & fees
Sep 23 - Sep 24
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

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

10/10 Excellent
"Conveniently located older hotel. Smaller rooms but very adequate. Friendly staff."
Robert K 1-night trip
Posted less than an hour ago
Hotel Saint Clair- Magnificent Mile

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:

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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 Gaelic Park.

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.