Crestwood Holiday Rentals

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Holiday Rentals in Crestwood

Aparthotel in Downtown Chicago

4.0 star property
9.2 out of 10, Wonderful, (1001)
"Beautiful view, and a very nice condo. "
United States
Tiffanie
The price is AU$253
includes taxes & fees
24 Dec - 25 Dec
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

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 AU$187
includes taxes & fees
11 Dec - 12 Dec
Chicago luxury home suites

Aparthotel in Downtown Chicago

4.0 star property
9.0 out of 10, Wonderful, (396)
"Clean room cool staff enjoyed my stay will come stay again. "
United States
Donald
Level Chicago – Old Town

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (1)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is AU$257
includes taxes & fees
1 Jan - 2 Jan 2026
1BR Modern Luxe Apt with In-Unit Laundry

Apartment in Downtown Chicago

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 AU$314
includes taxes & fees
14 Dec - 15 Dec
Twice as Nice: Chic 2BR Stay with Style & Space

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (2)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is AU$257
includes taxes & fees
1 Jan - 2 Jan 2026
Sun-Drenched 1BR Apartment

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (3)
"Pretty cool place to stay for a short trip ! Everything was close to where we were which made traveling a lot easier. Apartment is a pretty decent size I would recommend just 2-3 people. You can easily contact the host about anything and they’ll respond within a timely manner. The only down side of this place was the shower cleanliness itself. Overall, cool place not bad at all definitely a quick trip kind of thing!"
United States
Majanique M.
The price is AU$257
includes taxes & fees
1 Jan - 2 Jan 2026
West Loop Living – Bright 1BR

Apartment in Downtown Chicago

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 AU$257
includes taxes & fees
1 Jan - 2 Jan 2026
Stylish 1BR in West Loop

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (4)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is AU$252
includes taxes & fees
1 Jan - 2 Jan 2026
Gold Coast Living: Modern Studio Unit

Apartment in Downtown Chicago

9.0 out of 10, Wonderful, (2)
"We loved the property! It was well kept, clean, with a seamless check in and check out process! I wish the parking garage would have been closer but otherwise everything was great! Shout out to the host for his promptness with all my questions! I would recommend this place if they are looking for a place to stay! "
United States
Bridney K.
The price is AU$463
includes taxes & fees
8 Jan - 9 Jan 2026
South Loop Rooftop With In & Out Parking 1

Apartment in Downtown Chicago

2.0 star property
8.0 out of 10, Very good, (1)
"Great location, plenty of space and clean home. "
United States
Brittany T.
The price is AU$473
includes taxes & fees
17 Dec - 18 Dec
Modern West Loop Gem-City Views & Prime Location 5

Apartment in Downtown Chicago

9.6 out of 10, Exceptional, (4)
"Convenient location and clean place"
United States
David S.
The price is AU$257
includes taxes & fees
1 Jan - 2 Jan 2026
The One: A 1BR Stay That Feels Like Home

Apartment in Downtown Chicago

2.0 star property
The price is AU$554
includes taxes & fees
23 Dec - 24 Dec
Downtown Chicago Stay with Free In & Out Parking 3

Apartment in Downtown Chicago

8.4 out of 10, Very good, (8)
"Clean, simple space close to the parks at the waterfront (Millennium, Grant, etc) and several spots for coffee. A bit of an odd building location (it's in a dorm tower with a laundry space next door! Not noisy tho) but easy to access at all hours, nice view as pictured."
United States
Pip M.
The price is AU$632
includes taxes & fees
11 Dec - 12 Dec
Your Chicago get Away

Aparthotel in Downtown Chicago

4.0 star property
9.6 out of 10, Exceptional, (181)
"Awesome stay "
United States
Sally
Kasa River North Chicago

Aparthotel in West Town

2.0 star property
9.6 out of 10, Exceptional, (5)
"Cute little studio that was clean. There was a nice size kitchen and was close to our activities in the West loop of Chicago. There was also assistance with parking located in the lofts."
United States
Jennifer
The price is AU$328
includes taxes & fees
10 Dec - 11 Dec
Chicago Third Floor Studio by 747 Lofts

Apartment in Downtown Chicago

9.0 out of 10, Wonderful, (2)
"Awesome location, great place would definitely recommend will hopefully return"
United States
lucas c.
The price is AU$538
includes taxes & fees
14 Dec - 15 Dec
River North Rooftop With In and Out Parking 1

Apartment in Hyde Park

10.0 out of 10, Exceptional, (2)
"This apartment is a very basic rental unit – – had what we needed for our three nights stay, and we were very pleased. Great value for the money."
United States
Alan F.
The price is AU$251
includes taxes & fees
10 Dec - 11 Dec
Bright & Cozy 1BR Near UChicago

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (1)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveller
The price is AU$257
includes taxes & fees
4 Jan - 5 Jan 2026
Sleek 1BR Apt w/ Laundry

Apartment in Hyde Park

9.6 out of 10, Exceptional, (4)
"Nice place for a girls trip weekend. "
United States
Madonna A.
The price is AU$281
includes taxes & fees
16 Dec - 17 Dec
Sleek & Functional 2-Bedroom Apt
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

Find out more about Crestwood

Everything you need to know about Crestwood holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Crestwood holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Crestwood holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Crestwood holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Crestwood. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Crestwood holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Crestwood holiday rentals we have selected for you start as low as AU$144 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Crestwood rentals

At Expedia, we put the best Crestwood holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Crestwood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Crestwood holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Crestwood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

LakeHouse: This holiday home rental outside of Crestwood is located on the beach, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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 Abbott 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.