Crestwood Holiday Rentals

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Holiday Rentals in Crestwood

Sentral Michigan Avenue

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (983)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is NZ$296
includes taxes & fees
7 Dec - 8 Dec
Sentral Michigan Avenue

Level Chicago – Old Town

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (380)
"Property was clean, centrally located with wonderful staff. Will definitely stay again."
United States
Michelle
Level Chicago – Old Town

1BR Modern Luxe Apt with In-Unit Laundry

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 NZ$315
includes taxes & fees
17 Nov - 18 Nov
1BR Modern Luxe Apt with In-Unit Laundry

Gold Coast Living: Modern Studio Unit

Downtown Chicago
10.0 out of 10, Exceptional, (3)
"Perfect pet friendly pied-à-terre! This sweet studio comes highly recommended!!!!"
United States
Brandy
The price is NZ$291
includes taxes & fees
17 Nov - 18 Nov
Gold Coast Living: Modern Studio Unit

Kasa River North Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (178)
"Awesome stay "
United States
Sally
Kasa River North Chicago

West Loop Living – Bright 1BR

Downtown Chicago
10.0 out of 10, Exceptional, (1)
"Thorough and easy to follow parking and check in instructions. Clean apartment. "
United States
Kira V.
The price is NZ$315
includes taxes & fees
17 Nov - 18 Nov
West Loop Living – Bright 1BR

Sun-Drenched 1BR Apartment

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 NZ$321
includes taxes & fees
24 Nov - 25 Nov
Sun-Drenched 1BR Apartment

Stylish 1BR in West Loop

Downtown Chicago
10.0 out of 10, Exceptional, (9)
"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 NZ$315
includes taxes & fees
19 Nov - 20 Nov
Stylish 1BR in West Loop

The One: A 1BR Stay That Feels Like Home

Downtown Chicago
9.4 out of 10, Exceptional, (3)
"Convenient location and clean place"
United States
David S.
The price is NZ$315
includes taxes & fees
17 Nov - 18 Nov
The One: A 1BR Stay That Feels Like Home

Chicago luxury home suites

2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"This was Amazing stay I have ever had in my life. Wonderful host, super clean. Stunning views, close to everything that you would needed. "
New Zealand
Moha
The price is NZ$586
includes taxes & fees
17 Nov - 18 Nov
Chicago luxury home suites

Sleek 1BR Apt w/ Laundry

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 NZ$357
includes taxes & fees
14 Dec - 15 Dec
Sleek 1BR Apt w/ Laundry

South Loop Rooftop With In and Out Parking 3

Downtown Chicago
8.6 out of 10, Excellent, (4)
"Modern and stylish apartment in a great location. Lots of extra thoughtful touches made it a great stay. "
Australia
Angela M.
The price is NZ$562
includes taxes & fees
24 Nov - 25 Nov
South Loop Rooftop With In and Out Parking 3

River North Private Balcony With In and Out Parking

Downtown Chicago
10.0 out of 10, Exceptional, (3)
"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 NZ$661
includes taxes & fees
4 Dec - 5 Dec
River North Private Balcony With In and Out Parking

River North Rooftop With In and Out Parking 5

Downtown Chicago
10.0 out of 10, Exceptional, (2)
"As advertised. Beautiful, well appointed apartment. Centrally located to restaurants, shopping and the L train. Hosts were very communicative and attentive to our needs. Highly recommend. "
United States
Mike S.
The price is NZ$599
includes taxes & fees
11 Dec - 12 Dec
River North Rooftop With In and Out Parking 5

Your Chicago get Away

Downtown Chicago
8.4 out of 10, Very good, (8)
"We came to Chicago to visit museums and the apartment was clean and conveniently located. It had everything we needed for our stay. One note, parking is listed as an amenity. However, it wasn’t included, though there were many secure lots within a block to pay and park."
United States
Laura D.
The price is NZ$885
includes taxes & fees
24 Nov - 25 Nov
Your Chicago get Away

Vintage Studio in Chicago’s Gold Coast

Downtown Chicago
The price is NZ$291
includes taxes & fees
17 Nov - 18 Nov
Vintage Studio in Chicago’s Gold Coast

Bright & Cozy 1BR Near UChicago

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 NZ$315
includes taxes & fees
18 Nov - 19 Nov
Bright & Cozy 1BR Near UChicago

Bright & Modern 1BR in Hyde Park

Hyde Park
10.0 out of 10, Exceptional, (1)
"Great place to stay. It was easy to settle in and relax after a long day of traveling. The bed was comfortable and great to sleep on. Will definitely try for this property again if I need to come to the area."
United States
Michael S.
The price is NZ$317
includes taxes & fees
3 Dec - 4 Dec
Bright & Modern 1BR in Hyde Park

Contemporary 2BR Apartment in Vibrant Hyde Park

Hyde Park
10.0 out of 10, Exceptional, (1)
"We stayed in this comfortable, quiet apartment for four weeks when my husband was undergoing radiation treatments for cancer at the University of Chicago Medical Center. It was just what we needed. The location—a block from Lake Michigan with its endless miles of parks and green spaces—was spectacular, and we spent long hours walking our dogs and biking along the lake on the beautifully landscaped walking and biking trails. The apartment itself is well appointed, clean, and blessedly quiet...
United States
Heidi H.
The price is NZ$368
includes taxes & fees
17 Nov - 18 Nov
Contemporary 2BR Apartment in Vibrant Hyde Park

Twice as Nice: Chic 2BR Stay with Style & Space

Downtown Chicago
9.6 out of 10, Exceptional, (13)
"Had a very nice time in Chicago!"
United States
Valerie S.
The price is NZ$389
includes taxes & fees
1 Dec - 2 Dec
Twice as Nice: Chic 2BR Stay with Style & Space
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 favorite 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 depends 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 NZ$168 per night. Entering your travel dates in the search wizard you might find 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?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: This holiday home rental outside of Crestwood offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

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 Lake Katherine Nature Center. 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.