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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Crestwood vacation rentals

1 bedroom, desk, iron/ironing board, WiFi

1. Cozy Garden Unit 1st flr with private entrance and Turo vehicle available.

Cozy Garden Unit 1st flr with private entrance and Turo vehicle available.
Hickory Hills
9.6 out of 10, Exceptional, (8 reviews)
"Easy to locate shopping mall close by friendly neighborhood and safe. when you're looking at stay away from home that's where you want to be."
United States
Ralph
The price is AED 413
AED 717 total
includes taxes & fees
29 Sep - 30 Sep
Cozy Garden Unit 1st flr with private entrance and Turo vehicle available.
Dining

2. Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI

Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI
Berwyn
9.2 out of 10, Wonderful, (21 reviews)
"Great little place not far from downtown. Clean apartment and a comfortable bed. Daughter slept on the couch and said it wasn't too bad. Everything worked as expected with no issues. Can hear people walking up the steps from time to time but overall pretty quiet. Took some time to find a parking spot but not the host's fault. Overall a great experience and would stay again."
United States
Garrett C.
The price is AED 249
AED 620 total
includes taxes & fees
30 Sep - 1 Oct
Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI
2 bedrooms, iron/ironing board, WiFi (free), bed sheets

3. Romantic Escape - Adult Playhouse with Exotic Dungeon

Romantic Escape - Adult Playhouse with Exotic Dungeon
South Holland
8.8 out of 10, Excellent, (13 reviews)
"enjoyed my stay cant wait to book again "
United States
Anonymous traveler
The price is AED 1,576
AED 1,902 total
includes taxes & fees
24 Sep - 25 Sep
Romantic Escape - Adult Playhouse with Exotic Dungeon
Dining

4. Cozy Urban View Retreat Near Downtown - Sleeps 7

Cozy Urban View Retreat Near Downtown - Sleeps 7
Lawndale
The price is AED 270
AED 817 total
includes taxes & fees
30 Sep - 1 Oct
Cozy Urban View Retreat Near Downtown - Sleeps 7
Exterior

5. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,336 reviews)
"Great venue"
United States
Arthur Noel
The price is AED 559
AED 764 total
includes taxes & fees
27 Sep - 28 Sep
Sentral Michigan Avenue
Dining

6. Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
Berwyn
10.0 out of 10, Exceptional, (32 reviews)
"Relaxing stay and safe location. Host JD provided great communication throughout the stay. Stores are nearby in case you need items for your trip. Food options are abundant in the area. 30 min drive to downtown Chicago."
United States
Cynthia M.
The price is AED 280
AED 693 total
includes taxes & fees
13 Oct - 14 Oct
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
Smart TV, books

7. Stylish 2BR Near Hyde Park, UChicago & Lake

Stylish 2BR Near Hyde Park, UChicago & Lake
Woodlawn
10.0 out of 10, Exceptional, (7 reviews)
"Property looks recently renovated and has everything you need for a comfortable stay."
United States
Anna P.
The price is AED 617
AED 1,500 total
includes taxes & fees
29 Sep - 30 Sep
Stylish 2BR Near Hyde Park, UChicago & Lake
Game room

8. Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade

Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade
Brighton Park
9.4 out of 10, Exceptional, (13 reviews)
"It was great it had the basic amenities for a family to enjoy the stay"
United States
Damary T.
The price is AED 221
AED 957 total
includes taxes & fees
29 Sep - 30 Sep
Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade
Property grounds

9. Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Robertsdale
9.8 out of 10, Exceptional, (35 reviews)
"I had a fun stay "
United States
Jusu K.
The price is AED 526
AED 757 total
includes taxes & fees
29 Sep - 30 Sep
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Smart TV, books

10. Chic Suite/Mins to L Train /Laundry/Free Parking

Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9.4 out of 10, Exceptional, (71 reviews)
"Easy access to the Green Line."
United States
Michael
The price is AED 400
AED 921 total
includes taxes & fees
28 Sep - 29 Sep
Chic Suite/Mins to L Train /Laundry/Free Parking
Smart TV

11. Spacious 3br home near Chicago, fenced yard for pets

Spacious 3br home near Chicago, fenced yard for pets
Richton Park
9.0 out of 10, Wonderful, (28 reviews)
"Very spacious accommodations in a very nice neighborhood. Convenient to food and shopping. Great value for the cost. "
United States
Greg S.
The price is AED 757
AED 1,690 total
includes taxes & fees
20 Oct - 21 Oct
Spacious 3br home near Chicago, fenced yard for pets
Smart TV

12. Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW

Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
Berwyn
9.8 out of 10, Exceptional, (22 reviews)
"Great place to stay "
United States
Harquesha S.
The price is AED 249
AED 659 total
includes taxes & fees
6 Oct - 7 Oct
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
Coffee/tea maker, fridge, microwave, oven

13. Experience Forest Park living near Top Places like downtown Chicago

Experience Forest Park living near Top Places like downtown Chicago
Forest Park
9.4 out of 10, Exceptional, (18 reviews)
"Good location for visiting family just outside Chicago."
United States
Josh H.
The price is AED 496
AED 1,265 total
includes taxes & fees
27 Sep - 28 Sep
Experience Forest Park living near Top Places like downtown Chicago
Interior

14. Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP

Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Berwyn
9.4 out of 10, Exceptional, (40 reviews)
"Beautiful clean and comfy loved my stay"
United States
Tania W.
The price is AED 312
AED 747 total
includes taxes & fees
13 Oct - 14 Oct
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Coffee/tea maker, fridge, microwave, oven

15. Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (80 reviews)
"Excellent place to stay!"
United States
Alicia K.
The price is AED 413
AED 1,104 total
includes taxes & fees
28 Sep - 29 Sep
Cozy, Comfortable and Convenient apartment. Close to everything!
Smart TV

16. Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood
7.8 out of 10, Good, (33 reviews)
"Was a very nice stay and the host was very helpful and got very quick responses "
United States
Eduardo
The price is AED 545
AED 1,102 total
includes taxes & fees
28 Sep - 29 Sep
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Smart TV

17. Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
Westmont
9.4 out of 10, Exceptional, (3 reviews)
"Very welcoming and smells good, cozy feeling to it and quiet neighborhood."
United States
Tomas R.
The price is AED 452
AED 782 total
includes taxes & fees
30 Sep - 1 Oct
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
Interior

18. King Size Bed, Near Hwy, Work Desk, Parking Just A Few Feet Away

King Size Bed, Near Hwy, Work Desk, Parking Just A Few Feet Away
Lockport
10.0 out of 10, Exceptional, (10 reviews)
"We had a great stay. The host communicated well, property was clean, well stocked, and had plenty of space. If we were visiting this area again we would definitely stay here."
United States
Jennifer A.
The price is AED 460
AED 964 total
includes taxes & fees
28 Sep - 29 Sep
King Size Bed, Near Hwy, Work Desk, Parking Just A Few Feet Away
Coffee/tea maker, fridge, microwave, oven

19. Cozy Luxury 1BR - 10 Min to Downtown Chicago

Cozy Luxury 1BR - 10 Min to Downtown Chicago
Lawndale
7.8 out of 10, Good, (12 reviews)
"Don't miss out on this spot!! It's truly a must & great location!!! I really enjoyed my time here for real"
United States
Alexis R.
The price is AED 331
AED 912 total
includes taxes & fees
7 Oct - 8 Oct
Cozy Luxury 1BR - 10 Min to Downtown Chicago
Exterior

20. A quiet stay while you are away

A quiet stay while you are away
Oak Park
9.8 out of 10, Exceptional, (36 reviews)
"Excellent home! The neighborhood is great and the home has everything you need for a great stay. And if you have any questions, Jay is very good for getting back to you."
United States
Fred D.
The price is AED 487
AED 1,058 total
includes taxes & fees
12 Oct - 13 Oct
A quiet stay while you are away
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

8/10 Good
"Really nice hotel. Clean and comfortable staff was very helpful. Rooftop bar was a plus. It was also quiet."
Shandaka 1-night trip
Posted 2 hours ago
The Chicago Hotel Collection - Magnificent Mile

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.

What are some of the best vacation home rentals in Crestwood?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: Visitors like this Crestwood vacation home rental. It is located in the city center and has a balcony, a barbecue grill, 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 you can cook with friends or family.

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 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.