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

Crestwood Holiday Rentals

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Crestwood holiday rentals

Indoor pool

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,237 reviews)
"Great property and location."
United States
Michael
The price is HK$1,186
HK$1,622 total
includes taxes & fees
30 Aug - 31 Aug
Sentral Michigan Avenue
Coffee/tea maker, fridge, microwave, oven

2. *The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Worth
9.4 out of 10, Exceptional, (63 reviews)
"Checking in was easy, the place is as advertised, communication was easy as well, had no problems, will be staying there again. "
United States
Joe M.
The price is HK$1,568
HK$3,249 total
includes taxes & fees
9 Aug - 10 Aug
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Interior

3. Charming 2-bedroom apartment in marvelous Blue Island with WiFi

Charming 2-bedroom apartment in marvelous Blue Island with WiFi
Blue Island
7.0 out of 10, Good, (9 reviews)
"Appreciate the hospitality and the space !"
United States
Kaydon D.
The price is HK$1,157
HK$2,673 total
includes taxes & fees
11 Aug - 12 Aug
Charming 2-bedroom apartment in marvelous Blue Island with WiFi
Private kitchen

4. Soothing 1 bedroom apartment with AC in charming Oak Lawn,

Soothing 1 bedroom apartment with AC in charming Oak Lawn,
Oak Lawn
6.6 out of 10, (7 reviews)
The price is HK$1,059
HK$1,300 total
includes taxes & fees
5 Aug - 6 Aug
Soothing 1 bedroom apartment with AC in charming Oak Lawn,
Full-sized fridge, microwave, oven, stovetop

5. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (512 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 HK$2,131
HK$2,695 total
includes taxes & fees
24 Aug - 25 Aug
Level Chicago – Old Town
Smart TV, fireplace, video games, DVD player

6. Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax

Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax
Calumet Park
9.2 out of 10, Wonderful, (11 reviews)
"Cozy home, perfect for our stay. Highly recommend."
United States
Alisa G.
The price is HK$847
HK$1,972 total
includes taxes & fees
12 Aug - 13 Aug
Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax
Lake

7. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
7.8 out of 10, Good, (9 reviews)
"Great location and super clean!"
United States
Erica
The price is HK$2,455
HK$3,384 total
includes taxes & fees
2 Sept - 3 Sept
Kasa Lake Shore Chicago
TV, offices

8. LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
9.2 out of 10, Wonderful, (9 reviews)
"Super clean, great communication! Thanks for a great stay."
United States
Tracey L.
The price is HK$2,235
HK$3,001 total
includes taxes & fees
9 Aug - 10 Aug
LIVN West Loop Chicago 2 BR City View
Coffee/tea maker, fridge, microwave, oven

9. River North Rooftop With In and Out Parking 5

River North Rooftop With In and Out Parking 5
Downtown Chicago
9.8 out of 10, Exceptional, (6 reviews)
"Everything was amazing, property was even better than expected"
United States
Jacob
The price is HK$2,243
HK$4,544 total
includes taxes & fees
16 Aug - 17 Aug
River North Rooftop With In and Out Parking 5
TV, offices

10. LIVN Millennium Park Downtown Chicago 1 BR

LIVN Millennium Park Downtown Chicago 1 BR
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great location to sights, shops, and food."
United States
Adrianna W.
The price is HK$2,180
HK$2,927 total
includes taxes & fees
9 Aug - 10 Aug
LIVN Millennium Park Downtown Chicago 1 BR
TV, offices

11. River North Private Balcony With In and Out Parking

River North Private Balcony With In and Out Parking
Downtown Chicago
10.0 out of 10, Exceptional, (4 reviews)
"Place was easily accessible- very clean and an amazing alternative to hotel living for 2 colleagues. Coffee was available and all the basics of a hotel. "
United States
Rae M.
The price is HK$1,647
HK$3,712 total
includes taxes & fees
30 Aug - 31 Aug
River North Private Balcony With In and Out Parking
Interior

12. South Loop Rooftop With In and Out Parking 3

South Loop Rooftop With In and Out Parking 3
Downtown Chicago
8.8 out of 10, Excellent, (5 reviews)
"Clean place. Family friendly. Location was great. A lot of restaurants close by. Great communication from the host."
United States
jaspreet
The price is HK$1,584
HK$4,085 total
includes taxes & fees
19 Aug - 20 Aug
South Loop Rooftop With In and Out Parking 3
Dining

13. A Dream Home in Chicagoland

A Dream Home in Chicagoland
Homewood
6.0 out of 10, (6 reviews)
"Beautiful neighborhood. Property was just as described. Host was very accommodating to our needs. Quickly responded to me. Would highly recommend. Thank you again "
United States
Jennifer C.
The price is HK$1,575
HK$3,724 total
includes taxes & fees
25 Aug - 26 Aug
A Dream Home in Chicagoland
Dining

14. 3-bedroom house in lovely Matteson with cool AC breeze

3-bedroom house in lovely Matteson with cool AC breeze
Matteson
10.0 out of 10, Exceptional, (1 review)
"clean, comfortable, hosts very responsive to communications, neighborhood felt safe, perfect location for our stay to attend sectionals NTRP tennis tournament at HF Racquet and Fitness Club"
United States
Susan H.
The price is HK$2,729
HK$5,218 total
includes taxes & fees
1 Sept - 2 Sept
3-bedroom house in lovely Matteson with cool AC breeze
3 bedrooms, desk, iron/ironing board, WiFi

15. Downtown Chicago Stay with Free In & Out Parking 4

Downtown Chicago Stay with Free In & Out Parking 4
Downtown Chicago
9.6 out of 10, Exceptional, (7 reviews)
"Our stay was wonderful. The views were fantastic. The apartment was centrally located so we were able to walk to restaurants, museums, and theaters. We bookmarked this location for future stays."
United States
Renae S.
The price is HK$2,745
HK$5,536 total
includes taxes & fees
25 Aug - 26 Aug
Downtown Chicago Stay with Free In & Out Parking 4
TV, offices

16. Modern West Loop Gem-City Views & Prime Location 5

Modern West Loop Gem-City Views & Prime Location 5
Downtown Chicago
9.0 out of 10, Wonderful, (6 reviews)
"Great location, plenty of space and clean home. "
United States
Brittany T.
The price is HK$2,219
HK$5,895 total
includes taxes & fees
10 Aug - 11 Aug
Modern West Loop Gem-City Views & Prime Location 5
Dining

17. Plymouth Collection: 3BD 2BA High Floor with Gym

Plymouth Collection: 3BD 2BA High Floor with Gym
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"The suite was excellent. Clean and very well furnished. The building is located within walking distance to many of the things that we did. We would stay in this place again in a heartbeat. Very pleased with our experience"
United States
Derek M.
The price is HK$2,353
HK$4,971 total
includes taxes & fees
10 Aug - 11 Aug
Plymouth Collection: 3BD 2BA High Floor with Gym
TV

18. Spacious and Inviting

Spacious and Inviting
Willowbrook
10.0 out of 10, Exceptional, (1 review)
"I had family in from the West Coast. I would recommend. Very well decorated and very cozy. Nice outside deck with plenty of seating and large yard! It was great to be able to have family over and visit. Communication was very good also! Thank you! "
United States
karin e.
The price is HK$3,532
HK$6,843 total
includes taxes & fees
5 Aug - 6 Aug
Spacious and Inviting
1 bedroom, iron/ironing board, travel cot, WiFi

19. LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.4 out of 10, Exceptional, (16 reviews)
"Highly recommend! Will be staying here again."
United States
Sheila M.
The price is HK$1,521
HK$2,018 total
includes taxes & fees
10 Aug - 11 Aug
LIVN West Loop Chicago Queen Superior Studio
TV, offices

20. LIVN Millennium Park Downtown Chicago Superior 1BR

LIVN Millennium Park Downtown Chicago Superior 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Excelente, well located. Recommended."
United States
Sandra S.
The price is HK$2,133
HK$2,872 total
includes taxes & fees
9 Aug - 10 Aug
LIVN Millennium Park Downtown Chicago Superior 1BR
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 Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"Great location and clean & neat."
Nikolas 1-night trip
Posted 2 hours ago
The Chicago Hotel Collection - 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:

  • View our selection of featured holiday rentals in Crestwood
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  • 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.

What are some of the best holiday rentals that Crestwood has to offer?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This holiday home rental outside of Crestwood is located in the city centre, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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.