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
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Crestwood vacation rentals

A dining area with a wooden table and chairs, a ceiling fan, and a couch.

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

Charming 2-bedroom apartment in marvelous Blue Island with WiFi
Blue Island
6.4 out of 10, (11 reviews)
"Town was quite walkable which was fun. Teddy is very nice. "
United States
India L.
The price is AED 542
AED 1,150 total
includes taxes & fees
9 Nov - 10 Nov
Charming 2-bedroom apartment in marvelous Blue Island with WiFi
A hotel lobby with a reception desk, a staircase, and a small seating area.

2. 2 Full Beds | Non-Smoking

2 Full Beds | Non-Smoking
Harvey
10.0 out of 10, Exceptional, (4 reviews)
"Would tell anyone passing through to stop here. Nothing flashy but all essentials met our needs with no fuss. Clean bathroom, working TV, and decent parking spot included."
United States
Anonymous traveler
The price is AED 247
AED 280 total
includes taxes & fees
12 Nov - 13 Nov
2 Full Beds | Non-Smoking
A neatly arranged bedroom with a bed, bedside tables, and abstract wall art.

3. Hyde Park Trendy Studio Apartment in Good Spot

Hyde Park Trendy Studio Apartment in Good Spot
Hyde Park
10.0 out of 10, Exceptional, (1 review)
"Such a cozy stay! Definitely recommend!"
United States
Angelina
The price is AED 239
AED 554 total
includes taxes & fees
12 Nov - 13 Nov
Hyde Park Trendy Studio Apartment in Good Spot
A dining area with a table set for two, a black leather sofa, and a ceiling fan.

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

Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
Berwyn
9.8 out of 10, Exceptional, (35 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 264
AED 648 total
includes taxes & fees
16 Nov - 17 Nov
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
A living room with a grey sofa, two chairs, a coffee table, and a small side table.

5. Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
Brighton Park
10.0 out of 10, Exceptional, (2 reviews)
"The rooms were spotless. The apartment was spacious. I enjoyed my stay. "
United States
Rachel
The price is AED 231
AED 837 total
includes taxes & fees
9 Nov - 10 Nov
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
Game room

6. 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
9.6 out of 10, Exceptional, (14 reviews)
"Excellent communication from The Host on a beautiful property located close to everything you could want to do in Chicago. The check-in process was smooth and the host kept in constant communication to ensure that everything was Flawless from check in to check out"
United States
AJ B.
Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade
A compact kitchen with dark wood cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

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

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (82 reviews)
"Excellent place to stay!"
United States
Alicia K.
The price is AED 397
AED 992 total
includes taxes & fees
10 Nov - 11 Nov
Cozy, Comfortable and Convenient apartment. Close to everything!
A bedroom with a bed, a nightstand, a wall-mounted lamp, and a plant.

8. Romantic Escape - Adult Playhouse with Exotic Dungeon

Romantic Escape - Adult Playhouse with Exotic Dungeon
South Holland
8.8 out of 10, Excellent, (15 reviews)
"enjoyed my stay cant wait to book again "
United States
Anonymous traveler
The price is AED 1,432
AED 1,587 total
includes taxes & fees
9 Nov - 10 Nov
Romantic Escape - Adult Playhouse with Exotic Dungeon
A compact kitchen with a sink, a microwave, a refrigerator, a small table with stools, and a ceiling fan.

9. Beautiful Rustic Cabin for Two!

Beautiful Rustic Cabin for Two!
Griffith
8.4 out of 10, Very good, (35 reviews)
"It was a very nice property and was near many great places like Toast and Jam"
United States
jaco C.
The price is AED 305
AED 391 total
includes taxes & fees
6 Dec - 7 Dec
Beautiful Rustic Cabin for Two!
A modern living room with a grey sofa, a dining table with chairs, and a kitchen area with a kettle.

10. Perfect 1BR Spot near Attractions

Perfect 1BR Spot near Attractions
Hyde Park
6.0 out of 10, (1 review)
"I would characterize this property as “fine”. I only needed to stay one night for a business trip and it got the job done. Getting in/out was a little cumbersome with a lockbox to retrieve a set of keys. Hot water took quite a long time to heat up and deliver for a shower. Shower bathtub and amenities were lacking. Again, it got the job done for a night of sleep."
United States
Andrew M.
The price is AED 261
AED 819 total
includes taxes & fees
10 Nov - 11 Nov
Perfect 1BR Spot near Attractions
A modern living room with a grey sofa, a round wooden coffee table, and a patterned rug.

11. Laundry Room Access, Near Hwy, Convenient Parking Just A Few Feet Away

Laundry Room Access, Near Hwy, Convenient Parking Just A Few Feet Away
Lockport
The price is AED 391
AED 962 total
includes taxes & fees
12 Nov - 13 Nov
Laundry Room Access, Near Hwy, Convenient Parking Just A Few Feet Away
A modern living room with a grey sofa, a glass coffee table, and a potted plant.

12. Conveniently Situated 1BR Apartment

Conveniently Situated 1BR Apartment
Hyde Park
10.0 out of 10, Exceptional, (1 review)
"Cute, cozy place in walking distance to UChicago. Would stay here again."
United States
Jane L.
The price is AED 261
AED 778 total
includes taxes & fees
9 Nov - 10 Nov
Conveniently Situated 1BR Apartment
Kitchen

13. 1BR in Prime Hyde Park Apartment

1BR in Prime Hyde Park Apartment
Hyde Park
The price is AED 253
AED 769 total
includes taxes & fees
9 Nov - 10 Nov
1BR in Prime Hyde Park Apartment
A modern living room with a sofa, coffee table, and TV. There are windows with blinds, a radiator, and a plant.

14. Sleek & Functional 2-Bedroom Apt

Sleek & Functional 2-Bedroom Apt
Hyde Park
10.0 out of 10, Exceptional, (1 review)
"Great place, great location!"
United States
Lisa T.
The price is AED 327
AED 727 total
includes taxes & fees
9 Nov - 10 Nov
Sleek & Functional 2-Bedroom Apt
A neatly made bed with a black headboard, two fluffy pillows, and a stack of towels.

15. Bright & Spacious 2BR– Prime Hyde Park Location

Bright & Spacious 2BR– Prime Hyde Park Location
Hyde Park
The price is AED 320
AED 737 total
includes taxes & fees
9 Nov - 10 Nov
Bright & Spacious 2BR– Prime Hyde Park Location
A modern living room with a grey sofa, white and patterned cushions, a round coffee table, and a ceiling fan.

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

Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9.6 out of 10, Exceptional, (75 reviews)
"Had an amazing stay and would definitely book again!"
United States
Makenna
The price is AED 317
AED 780 total
includes taxes & fees
17 Nov - 18 Nov
Chic Suite/Mins to L Train /Laundry/Free Parking
A hotel room with a bed, desk, chair, and a ceiling fan.

17. Cozy King bed,Nsmk|Kitchen|Studio 6 Chicago

Cozy King bed,Nsmk|Kitchen|Studio 6 Chicago
Chicago
9.8 out of 10, Exceptional, (28 reviews)
"Great staff clean rooms"
United States
Anonymous traveler
The price is AED 315
AED 348 total
includes taxes & fees
12 Nov - 13 Nov
Cozy King bed,Nsmk|Kitchen|Studio 6 Chicago
A modern hotel room with a large bed, a sitting area with a table and chairs, a kitchenette, and artwork on the wall.

18. Cozy Charm Studio Apt in Chicago

Cozy Charm Studio Apt in Chicago
Hyde Park
The price is AED 275
AED 795 total
includes taxes & fees
15 Nov - 16 Nov
Cozy Charm Studio Apt in Chicago
A modern building with the name 'SENIORAL' prominently displayed on the facade.

19. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,406 reviews)
"10/10 2nd time staying here!"
United States
Rosa
The price is AED 467
AED 548 total
includes taxes & fees
7 Dec - 8 Dec
Sentral Michigan Avenue
A waterfront promenade with high-rise buildings, a sandy beach, and a pedestrian walkway.

20. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (85 reviews)
"The bathroom was really clean. The beds were really comfortable"
United States
Jair
The price is AED 558
AED 882 total
includes taxes & fees
22 Nov - 23 Nov
Kasa Lake Shore Chicago
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

8/10 Good
"Our stay started off not the best but the staff went above and beyond to fix the mistakes. When we checked in the room was very tight and not the best kept. Expedia didnt give the best description of the room so it wasnt the fault of the hotel. The first night was awful though due to our ac being broken, the room was extremely hot and it was hard to sleep. We went down to complaint he next morning and the staff was extremely kind and helpful in getting us switched to a new room. The next room had the same issue, the ac was not working. so we got moved to another room. The next room we stayed in they had upgraded us due to the inconvenience. This room was much bigger and the ac finally worked! The staff being so kind and helpful made us want to stay again. The hotel is older so of course its not going to be perfect but i can handle the hotel not being perfect when the staff actually cares enough to try to make the stay as comfortable as possible. because of that i will be staying at this location again!"
Julia 3-night trip
Posted 6 hours ago
Hotel Saint Clair- 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 Marquette 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.