Crestwood Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Crestwood

Sentral Michigan Avenue
Interior
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, 443 reviews
"Great location and the view was fabulous! We had a very comfortable stay. Communication was excellent."
The price is RM761
RM1,031 total
includes taxes & fees
17 Jun - 18 Jun
Sentral Michigan Avenue
Sonder Market Hall
Interior
Sonder Market Hall
3.5 star property
8.4 out of 10, Very good, 96 reviews
"The property was very clean and I loved the fact that it had a kitchen for you to cook. What I did not like was that there was no market close enough to buy groceries. I also didn't like the fact that the TV was not accesible for us, even though, I payed the late fees for a late check out. "
The price is RM498
RM585 total
includes taxes & fees
8 Jul - 9 Jul
Sonder Market Hall
Sonder South Wabash
Interior
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, 315 reviews
"Comfortable to stay"
The price is RM753
RM884 total
includes taxes & fees
2 Jul - 3 Jul
Sonder South Wabash
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Kasa Magnificent Mile Chicago
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, 259 reviews
"The location is great and the room is fully equipped with the useful home appliances like dish washer, laundry and dryer. It’s very helpful for the long stay travelers."
Kasa Magnificent Mile Chicago
Level Chicago – Old Town
Front of property – evening/night
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, 217 reviews
"Great room - fabulous fitness center. Easy access to grocery stores to stock fridge. Room is furnished with all amenities. "
The price is RM1,269
RM1,571 total
includes taxes & fees
18 Jun - 19 Jun
Level Chicago – Old Town
Found Chicago powered by Sonder
Interior
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, 135 reviews
"I loved my stay at Found Chicago! The logistical communication was easy to understand and implement, and I liked that it was contactless. It was nice to use my PIN code for room entrance instead of keeping track of a key. The WiFi was sufficient for remote meetings on my laptop. And all of the amenities (lobby access, luggage locker, and printer) were convenient and easy to use. I highly recommend this hotel, and I'll plan to stay here again. "
The price is RM530
RM623 total
includes taxes & fees
14 Jul - 15 Jul
Found Chicago powered by Sonder
Sonder The Burnham
Individually decorated, individually furnished, free cots/infant beds
Sonder The Burnham
3.5 star property
9.0 out of 10, Wonderful, 80 reviews
"The stay was straight forward. Login with the passcode and get in. But no one at the reception so some nuances are not easy. For e.g. no early check in even if there are rooms. Also, for long stays, they cant change sheets or towels and no cleaning. It is an interesting concept but not so sure about long term stays like 4-5 days"
The price is RM1,010
RM1,186 total
includes taxes & fees
30 Jun - 1 Jul
Sonder The Burnham
The Neighborhood Hotel-Little Italy
50-inch Smart TV with satellite channels
The Neighborhood Hotel-Little Italy
2.0 star property
9.8 out of 10, Exceptional, 36 reviews
"Spacious, modern, bright, well stocked with utensils, pots and pans, towels, soaps, coffee etc. Only one elevator for many units and in case of malfunction, problematic. Overall, great concept with electronic access. The apartments/suites are beautifully appointed. "
The Neighborhood Hotel-Little Italy
Kasa River North Chicago
Exterior
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, 68 reviews
"Room was great! Spacious, clean and perfect for a night or longer stay. View was also very nice!"
Kasa River North Chicago
Sonder Jewelers Row
Exterior
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very good, 111 reviews
"We had a wonderful stay in the very comfortable apartment. I chose it for the location near Millenium Park and because it was a one bedroom. The apartment had excellent furnishings and faciilties. We had two difficulties during our stay, with the AC and with the washing machine, and both were solved quickly by the staff. They were responsive and went the extra mile to be sure everything was okay. We were also right over the L train, but with AC running I didn’t even notice it and slept great....
The price is RM852
RM1,000 total
includes taxes & fees
7 Jul - 8 Jul
Sonder Jewelers Row
Kasa South Loop Chicago
Living area
Kasa South Loop Chicago
4.0 star property
9.2 out of 10, Wonderful, 165 reviews
"Highly recommend! Amazing view of the city and the lake, clean and quiet yet close to everything. Thoughtfully furnished with nice surprises like power strips, white noise machine in bedroom, electric kettle etc. It was ideal and we’d stay there again. "
Kasa South Loop Chicago
Sonder The Plymouth
City view from property
Sonder The Plymouth
3.5 star property
8.4 out of 10, Very good, 68 reviews
"Great place to stay and visit Chicago on foot. The property was exactly what we hoped for. "
The price is RM666
RM782 total
includes taxes & fees
15 Jul - 16 Jul
Sonder The Plymouth
Sonder The Opal
Full-sized fridge, oven, stovetop, dishwasher
Sonder The Opal
3.5 star property
8.2 out of 10, Very good, 15 reviews
"I like that was contactless and easy to access. "
The price is RM977
RM1,147 total
includes taxes & fees
1 Jul - 2 Jul
Sonder The Opal
Sonder Greektown
40-inch flat-screen TV with digital channels, TV
Sonder Greektown
3.5 star property
8.8 out of 10, Excellent, 29 reviews
"LOCATION was terrific - central and close to all our 'outings'. Downside was NOT being able to control the thermostat. And NO response to any of our efforts to contact the property manger(s)."
The price is RM1,010
RM1,186 total
includes taxes & fees
2 Jul - 3 Jul
Sonder Greektown
Ground Floor Studios in Chicago by 747 Lofts
Exterior
Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
9.8 out of 10, Exceptional, 8 reviews
"Easy to check in, good information for parking in the area. The place was clean and nice."
The price is RM547
RM1,296 total
includes taxes & fees
26 Jun - 27 Jun
Ground Floor Studios in Chicago by 747 Lofts
Don't see what you're looking for?
See all available properties in Crestwood
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.

Other types of properties in Crestwood you may be interested in

Congress Plaza Hotel
Lobby
Congress Plaza Hotel
3.5 star property
7.6 out of 10, Good, 6,991 reviews
"Great values. "
The price is RM778
RM914 total
includes taxes & fees
17 Jun - 18 Jun
Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North
Lobby
Embassy Suites by Hilton Chicago Downtown River North
4.0 star property
8.0 out of 10, Very good, 2,391 reviews
"Nice omelette, breakfast and happy hour drinks."
The price is RM972
RM1,142 total
includes taxes & fees
1 Jul - 2 Jul
Embassy Suites by Hilton Chicago Downtown River North
River Hotel
View from property
River Hotel
4.0 star property
8.8 out of 10, Excellent, 2,956 reviews
"Perfect place with a water view. Walkable "
The price is RM767
RM900 total
includes taxes & fees
2 Jul - 3 Jul
River Hotel
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.

Search for holiday rentals in Crestwood on Expedia.co.uk! 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 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.

Recent reviews of Crestwood properties
Expedia verified reviews

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

5/5 Excellent
"We had a pleasant stay here! Staff were friendly and our room and amenities are very clean. Location was also convenient. It’s walking distance to many places in downtown and very easy to get rideshare/taxi service right outside of the property. "
A verified traveller stayed at The Royal Sonesta Chicago Downtown
Posted 18 hours ago
The Royal Sonesta Chicago Downtown