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
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Crestwood vacation rentals

Exterior

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,273 reviews)
"Nice stay"
United States
Heather
The price is ₩214,130
₩292,928 total
includes taxes & fees
Sep 7 - Sep 8
Sentral Michigan Avenue
Full-size fridge, microwave, oven, stovetop

2. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (518 reviews)
"We only stayed one night but we definitely want to go back and stay at least two nights. It really was beautiful, clean and very secure."
United States
Martha
The price is ₩336,967
₩430,505 total
includes taxes & fees
Sep 1 - Sep 2
Level Chicago – Old Town
Lake

3. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very Good, (15 reviews)
"Great location and super clean!"
United States
Erica
The price is ₩254,348
₩386,369 total
includes taxes & fees
Aug 20 - Aug 21
Kasa Lake Shore Chicago
Studio | Interior

4. 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 ₩132,860
₩244,770 total
includes taxes & fees
Sep 2 - Sep 3
Cabin 105 by 747 Lofts
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 ₩341,861
₩670,768 total
includes taxes & fees
Aug 24 - Aug 25
Classic Forest Park Foursquare < 1 Mi to Blue Line
Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Exterior

6. 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
Historic Oak Park Residence
Studio | Living area

7. 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, (25 reviews)
"It’s a really nice place. Its quite a distance from downtown Chicago. But it’s like 3 minutes from Chicago Blue line and a minute away from the bus station. Food is not a problem since there is a Korean grocery nearby. There is also a nearby Catholic church. The ameneties in this loft hotel is complete so if you are looking for a budget style trip and accommodation, I highly recommend this place."
United States
Joel
The price is ₩222,414
₩355,381 total
includes taxes & fees
Sep 10 - Sep 11
Ground Floor Studios in Chicago by 747 Lofts
Apartment, Private Bathroom | Lounge

8. 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 ₩315,501
₩518,457 total
includes taxes & fees
Aug 25 - Aug 26
At Home in Oak Park
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

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent
"Free coffee Free printing Early check in fee available"
Sean 1-night trip
Posted 2 hours ago
Crowne Plaza Chicago West Loop by IHG

Find out more about Crestwood

Search for Vacation rentals in Crestwood on Expedia.co.uk! You can easily find your home rentals, villas, Vacation apartments in Crestwood using one of the methods below:

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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.