Crestwood Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Crestwood vacation rentals

Indoor pool
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1006)
"Beautiful view, and a very nice condo. "
United States
Tiffanie
The price is ￥18,371
￥26,128 total
includes taxes & fees
Dec 21 - Dec 22
Sentral Michigan Avenue
Front of property - evening/night
Level Chicago – Old Town

Aparthotel in Downtown Chicago

Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (397)
"Clean room cool staff enjoyed my stay will come stay again. "
United States
Donald
Level Chicago – Old Town
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago

Aparthotel in Downtown Chicago

Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (650)
"Great location and place "
United States
Robert
Kasa Magnificent Mile Chicago
Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Balcony
Kasa South Loop Chicago

Aparthotel in Downtown Chicago

Kasa South Loop Chicago
4.0 star property
9.4 out of 10, Exceptional, (387)
"Great apartment, great view, close to good amenities, very safe."
United Kingdom
Ian
Kasa South Loop Chicago
Free WiFi, bed sheets
Chicago luxury home suites

Aparthotel in Downtown Chicago

Chicago luxury home suites
2.0 star property
7.4 out of 10, Good, (3)
"Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job."
Canada
pouya
The price is ￥20,467
￥24,026 total
includes taxes & fees
Dec 15 - Dec 16
Chicago luxury home suites
Property entrance
The Neighborhood Hotel-Little Italy

Aparthotel in Near West Side

The Neighborhood Hotel-Little Italy
4.0 star property
9.6 out of 10, Exceptional, (224)
"great place- excellent rooms and near tons of dining "
United States
chris
The Neighborhood Hotel-Little Italy
Business center
Kasa River North Chicago

Aparthotel in Downtown Chicago

Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (182)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Comfort Double Room | Desk, laptop workspace, blackout drapes, free WiFi
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Aparthotel in Harvey

Comfort Inn Chicago Southland I-80 & I-294 Near Casino
3.0 star property
3.8 out of 10, (67)
"Good "
United States
Abel
The price is ￥13,154
￥14,862 total
includes taxes & fees
Dec 13 - Dec 14
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Terrace/patio
NEW LUXURY PENTHOUSE CONDO

Condo in West Town

NEW LUXURY PENTHOUSE CONDO
10.0 out of 10, Exceptional, (200)
"Great house with a great rooftop. "
United States
Francisco
NEW LUXURY PENTHOUSE CONDO
Classic Apartment | Private kitchen
Stylish Apartment near Chicago Downtown

Aparthotel in Bridgeport

Stylish Apartment near Chicago Downtown
2.0 star property
Stylish Apartment near Chicago Downtown
Interior
Twice as Nice: Chic 2BR Stay with Style & Space

Apartment in Downtown Chicago

Twice as Nice: Chic 2BR Stay with Style & Space
9.6 out of 10, Exceptional, (14)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
The price is ￥12,284
￥32,020 total
includes taxes & fees
Dec 16 - Dec 17
Twice as Nice: Chic 2BR Stay with Style & Space
Outdoor dining
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

Apartment in Near West Side

3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
10.0 out of 10, Exceptional, (270)
"Beautiful property fully loaded with amenities."
United States
Allie P.
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
TV, offices
Modern West Loop Gem-City Views & Prime Location 6

Apartment in Downtown Chicago

Modern West Loop Gem-City Views & Prime Location 6
2.0 star property
10.0 out of 10, Exceptional, (6)
"Great place. Very comfortable & really nice location- loved the corner coffee shop "
United States
Sandra
Modern West Loop Gem-City Views & Prime Location 6
Interior
Urban Farm Fun with Goats 10 Minutes To Downtown!

Apartment in East Garfield Park

Urban Farm Fun with Goats 10 Minutes To Downtown!
7.8 out of 10, Good, (9)
"Great space, inside and out. Very kind friendly hosts. This was an amazing experience and we are grateful to Nicky and Drew for being so welcoming. "
United States
Jamie A.
Urban Farm Fun with Goats 10 Minutes To Downtown!
Interior
Art Villa

Aparthotel in West Town

Art Villa
5.0 star property
10.0 out of 10, Exceptional, (2)
Art Villa
Dining
55-56 Mag Mile Penthouse

Apartment in Downtown Chicago

55-56 Mag Mile Penthouse
10.0 out of 10, Exceptional, (300)
"Great location, great property, great views. "
United States
Mark D.
55-56 Mag Mile Penthouse
Interior
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Vacation Home in Near North Side

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
9.4 out of 10, Exceptional, (106)
"Awesome space for our large group! Location couldn’t have been better - on a very nice street with tons of bars and restaurants near by."
United States
Elias P.
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Fridge, microwave, oven, stovetop
Stylish 1BR in West Loop

Apartment in Downtown Chicago

Stylish 1BR in West Loop
10.0 out of 10, Exceptional, (10)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
United States
Jacob D.
The price is ￥9,796
￥26,197 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Stylish 1BR in West Loop
2 bedrooms, WiFi, wheelchair access
Charming 2-bedroom apartment in marvelous Blue Island with WiFi

Apartment in Blue Island

Charming 2-bedroom apartment in marvelous Blue Island with WiFi
7.6 out of 10, Good, (4)
"Only issue was the water pressure in the bathroom was very very low. "
United States
Derrick M.
The price is ￥22,950
￥53,496 total
includes taxes & fees
Dec 13 - Dec 14
Charming 2-bedroom apartment in marvelous Blue Island with WiFi
Microwave, oven, stovetop, dishwasher
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Vacation Home in Maywood

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
8.0 out of 10, Very Good, (19)
"Very nice place "
United States
Elliot H.
The price is ￥23,090
￥37,013 total
includes taxes & fees
Dec 13 - Dec 14
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
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

Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop

10/10 Excellent
"Cleanliness of the room "
ciera 1-night trip
Posted 3 hours ago
Homewood Suites by Hilton Chicago Downtown South Loop

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
  • Use the map to find apartments and other holiday homes in the Crestwood neighbourhood you prefer
  • 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 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?

LakeHouse: Visitors like this Crestwood vacation home rental. It is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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 Abbott Park. In the larger area, you’ll find Soldier Field and Trinity Christian College.

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.