A serene lake with reflections of trees and a cloudy sky.

Crestwood Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Crestwood holiday rentals

TV, offices

River North Rooftop With In and Out Parking 1

River North Rooftop With In and Out Parking 1
Downtown Chicago
9.8 out of 10, Exceptional, (7 reviews)
"Awesome location, great place would definitely recommend will hopefully return"
United States
lucas c.
The price is HK$1,638
HK$3,565 total
includes taxes & fees
10 Aug - 11 Aug
River North Rooftop With In and Out Parking 1
Interior

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
Near North Side
9.6 out of 10, Exceptional, (8 reviews)
"Excellent, clean, modern, fully furnished apartment in downtown Chicago that is a short car ride or walk to anything you need or want to visit. The neighborhood and building are very safe and the covered parking is well worth the extra expense. We loved the extra space to spread out and the skyline views were beautiful at night. The staff responded right away to any questions we had and even helped to accommodate us an extra night when an event kept us in town longer. The beds were comfortable...
United States
Kathryn
4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,216 reviews)
"Clean room, great staff, family-friendly, pet-friendly, and great rooms with a kitchen and wonderful showers. Great location!"
United States
Alessandra
The price is HK$1,123
HK$1,548 total
includes taxes & fees
17 Aug - 18 Aug
Sentral Michigan Avenue
1 bedroom, iron/ironing board, travel cot, WiFi

LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.2 out of 10, Wonderful, (13 reviews)
"Beautiful place exciting city everything was wonderful"
United States
Kyna C.
The price is HK$1,333
HK$1,777 total
includes taxes & fees
19 Jul - 20 Jul
LIVN West Loop Chicago Queen Superior Studio
TV, offices

LIVN Millennium Park Downtown Chicago 1 BR

LIVN Millennium Park Downtown Chicago 1 BR
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great location to sights, shops, and food."
United States
Adrianna W.
The price is HK$1,317
HK$1,759 total
includes taxes & fees
19 Jul - 20 Jul
LIVN Millennium Park Downtown Chicago 1 BR
Smart TV

Luxury Retreat w/ King Bed, 3-in-1 Pool Table, 15 Min to Chicago, Free Parking

Luxury Retreat w/ King Bed, 3-in-1 Pool Table, 15 Min to Chicago, Free Parking
Oak Park
The price is HK$832
HK$2,120 total
includes taxes & fees
29 Jul - 30 Jul
Luxury Retreat w/ King Bed, 3-in-1 Pool Table, 15 Min to Chicago, Free Parking
TV, offices

Modern West Loop Gem-City Views & Prime Location 5

Modern West Loop Gem-City Views & Prime Location 5
Downtown Chicago
9.0 out of 10, Wonderful, (6 reviews)
"Great location, plenty of space and clean home. "
United States
Brittany T.
The price is HK$2,524
HK$6,153 total
includes taxes & fees
10 Aug - 11 Aug
Modern West Loop Gem-City Views & Prime Location 5
Private kitchen

Soothing 1 bedroom apartment with AC in charming Oak Lawn,

Soothing 1 bedroom apartment with AC in charming Oak Lawn,
Oak Lawn
9.0 out of 10, Wonderful, (2 reviews)
"The host was very friendly and helpful. There was a massive storm before and the host accommodated us with everything we needed"
United States
Bailey H.
The price is HK$1,094
HK$1,338 total
includes taxes & fees
22 Jul - 23 Jul
Soothing 1 bedroom apartment with AC in charming Oak Lawn,
Dining

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Belmont Cragin
8.8 out of 10, Excellent, (3 reviews)
"I called the host about the thermostat not working and he said he would get in touch with somebody, never heard back from him and the problem was never solved. There were two window air conditioning units that I cleaned the filters myself as they were not very efficient."
United States
Raymond
The price is HK$550
HK$2,993 total
includes taxes & fees
27 Jul - 28 Jul
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Fridge, microwave, oven, stovetop

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Worth
9.4 out of 10, Exceptional, (63 reviews)
"Checking in was easy, the place is as advertised, communication was easy as well, had no problems, will be staying there again. "
United States
Joe M.
The price is HK$1,568
HK$3,172 total
includes taxes & fees
9 Aug - 10 Aug
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Smart TV, fireplace, video games, DVD player

Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax

Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax
Calumet Park
9.0 out of 10, Wonderful, (10 reviews)
"Lakeia was very accommodating throughout our stay."
United States
Timothy K.
The price is HK$988
HK$2,172 total
includes taxes & fees
28 Jul - 29 Jul
Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax
TV

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 HK$753
HK$2,294 total
includes taxes & fees
4 Aug - 5 Aug
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
Interior

South Loop Rooftop With In and Out Parking 3

South Loop Rooftop With In and Out Parking 3
Downtown Chicago
8.8 out of 10, Excellent, (5 reviews)
"Clean place. Family friendly. Location was great. A lot of restaurants close by. Great communication from the host."
United States
jaspreet
The price is HK$2,054
HK$4,654 total
includes taxes & fees
16 Aug - 17 Aug
South Loop Rooftop With In and Out Parking 3
Coffee/tea maker, fridge, microwave, oven

River North Private Deck With In and Out Parking

River North Private Deck With In and Out Parking
Downtown Chicago
9.8 out of 10, Exceptional, (12 reviews)
"Excellent location, very clean, spacious."
United States
John David K.
The price is HK$3,700
HK$7,229 total
includes taxes & fees
23 Jul - 24 Jul
River North Private Deck With In and Out Parking
Property grounds

Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Robertsdale
9.8 out of 10, Exceptional, (27 reviews)
"I had a fun stay "
United States
Jusu K.
The price is HK$1,247
HK$1,703 total
includes taxes & fees
17 Aug - 18 Aug
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
1 bedroom

Cozy King bed,Nsmk|Kitchen|Shower|Studio 6 Chicago

Cozy King bed,Nsmk|Kitchen|Shower|Studio 6 Chicago
Chicago
9.6 out of 10, Exceptional, (28 reviews)
"Nice, clean, and a quiet hotel"
United States
Anonymous traveller
The price is HK$822
HK$909 total
includes taxes & fees
12 Aug - 13 Aug
Cozy King bed,Nsmk|Kitchen|Shower|Studio 6 Chicago
Smart TV

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood
8.0 out of 10, Very good, (29 reviews)
"Pros: Quiet neighborhood, felt safe going in and out of the house. Upstairs bathroom shower was amazing. Cons: warmer in living room, stained pillows, couches and floors felt like dust mites all over( simple fix) All in all it was a good stay."
United States
Amal
The price is HK$1,164
HK$2,361 total
includes taxes & fees
20 Jul - 21 Jul
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Interior

Downtown Chicago Stay with Free In & Out Parking 1

Downtown Chicago Stay with Free In & Out Parking 1
Downtown Chicago
9.0 out of 10, Wonderful, (2 reviews)
"My overall experience was great! This 4 bedroom apartment.2 bath with included parking is a great place to stay when you are visiting Chicago and doing activities in the city.The management staff was great to work with. The front desk staff was also great.My family felt safe and we would return.Thigpen Family"
United States
Kimberly T.
The price is HK$2,563
HK$5,691 total
includes taxes & fees
28 Jul - 29 Jul
Downtown Chicago Stay with Free In & Out Parking 1
Interior

King Size Bed, Near Hwy, Work Desk, Parking Just A Few Feet Away

King Size Bed, Near Hwy, Work Desk, Parking Just A Few Feet Away
Lockport
10.0 out of 10, Exceptional, (9 reviews)
"Great stay. Nice place. Easy access. Clean. "
United States
Juan S.
The price is HK$983
HK$2,057 total
includes taxes & fees
20 Jul - 21 Jul
King Size Bed, Near Hwy, Work Desk, Parking Just A Few Feet Away
Coffee/tea maker, fridge, microwave, oven

Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (77 reviews)
"The host responded quickly to my requests. Apartment was clean. Kitchen well stocked with cooking, utensils, spices, etc. He registered my car so I coiud park on the street without any problem. Close to the Blue Line stop to take the "L" into downtown Chicago."
United States
Michael
The price is HK$1,101
HK$2,660 total
includes taxes & fees
27 Jul - 28 Jul
Cozy, Comfortable and Convenient apartment. Close to everything!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Crestwood Hotel Reviews

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

10/10 Excellent
"what a great location, and the rooftop bar was sensational. Service was friendly and solid, breakfast was enough to last you till dinner, and the rooms (especially the showers) were great."
Janna 3-night trip
Posted less than an hour ago
Hotel Riu Plaza Chicago

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 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?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This holiday home rental outside of Crestwood is located in the city centre, and has a balcony, a BBQ 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 that you can cook with friends or family.

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 Centennial 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.