Crestwood Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Crestwood

Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (568)
"Very great place to stay!"
United States
Edwin
Kasa Magnificent Mile Chicago
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (960)
"Great location and cleanliness of rooms. Staff was extremely helpful "
United States
Amy
The price is AU$289
includes taxes & fees
10 Nov - 11 Nov
Sentral Michigan Avenue
Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (367)
"Friendly staff and great amenities "
United States
Bryan
Level Chicago – Old Town
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
3.5 star property
8.0 out of 10, Very good, (385)
"Great stay!"
United States
Joe
The price is AU$198
includes taxes & fees
2 Nov - 3 Nov
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Sonder by Marriott Bonvoy The Burnham Apartments Loop
3.5 star property
8.8 out of 10, Excellent, (240)
"Great stay. "
United States
Teresa
The price is AU$244
includes taxes & fees
2 Nov - 3 Nov
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
3.5 star property
8.6 out of 10, Excellent, (690)
"Location was nice."
United States
Juliet
The price is AU$244
includes taxes & fees
2 Nov - 3 Nov
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Kasa South Loop Chicago
4.0 star property
9.4 out of 10, Exceptional, (363)
"An excellent place to stay in Chicago downtown."
United States
ABDULHAFEEZ
Kasa South Loop Chicago
The Neighborhood Hotel-Little Italy
4.0 star property
9.6 out of 10, Exceptional, (211)
"Perfect location and area was wonderful."
United States
Thomas
The Neighborhood Hotel-Little Italy
Sonder by Marriott Bonvoy The Opal Apartments River North
3.5 star property
8.4 out of 10, Very good, (53)
"Place was in a great location close to good restaurants "
United States
Charles
The price is AU$229
includes taxes & fees
16 Nov - 17 Nov
Sonder by Marriott Bonvoy The Opal Apartments River North
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (171)
"This place has everything for a multi-night stay."
United States
Dane
Kasa River North Chicago
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
3.5 star property
8.2 out of 10, Very good, (184)
"Place was amazing! Very centralized, all sorts of restaurants nearby, and right next to the CTA Trains which is AWESOME!"
United States
Alexander
The price is AU$213
includes taxes & fees
2 Nov - 3 Nov
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
3.0 star property
3.8 out of 10, (64)
"Good "
United States
Abel
The price is AU$147
includes taxes & fees
20 Oct - 21 Oct
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Stylish Apartment near Chicago Downtown
2.0 star property
The price is AU$522
includes taxes & fees
19 Oct - 20 Oct
Stylish Apartment near Chicago Downtown
Sonder by Marriott Bonvoy Greektown Apartments
3.5 star property
8.6 out of 10, Excellent, (65)
"The kitchen had everything we needed, great space overall, safe location, clean, near everything we needed, access to bus and rail very close, we really enjoyed our stay. "
United States
Samuel
The price is AU$244
includes taxes & fees
2 Nov - 3 Nov
Sonder by Marriott Bonvoy Greektown Apartments
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
3.5 star property
7.6 out of 10, Good, (144)
"Very clean and affordable "
United States
Matthew
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Cozy Studio in Hyde Park-Walk to Lake & University
9.0 out of 10, Wonderful, (7)
"This place was nice and clean and close to what I needed to do. I appreciated that it was affordable. "
United States
Nancy
The price is AU$276
includes taxes & fees
19 Oct - 20 Oct
Cozy Studio in Hyde Park-Walk to Lake & University
NEW LUXURY PENTHOUSE CONDO
10.0 out of 10, Exceptional, (197)
"Great house with a great rooftop. "
United States
Francisco
NEW LUXURY PENTHOUSE CONDO
Art Villa
5.0 star property
10.0 out of 10, Exceptional, (2)
" "
United States
tomonobu
The price is AU$1,586
includes taxes & fees
24 Oct - 25 Oct
Art Villa
Twice as Nice: Chic 2BR Stay with Style & Space
9.4 out of 10, Exceptional, (9)
"Had a very nice time in Chicago!"
United States
Valerie S.
The price is AU$349
includes taxes & fees
20 Oct - 21 Oct
Twice as Nice: Chic 2BR Stay with Style & Space
Chicago Luxury Penthouse Massive Rooftop Walk to Beach and Restaurants
10.0 out of 10, Exceptional, (2)
"I used to live in Chicago and have a short term rental in Ohio myself. This place is legit. This property is in the best location close to beach restaurants and bars. Perfect for college reunion. Rooftop was awesome place for us to catch up over coffee and plan the day. The kitchen has everything we needed. Speakers throughout was a nice touch. I can’t be more complementary of the hosts responsiveness and helpfulness. We would definitely stay here again."
United States
Justin F.
Chicago Luxury Penthouse Massive Rooftop Walk to Beach and Restaurants
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.
Save an average of 15% on thousands of hotels when you're signed in

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 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?

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.

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.