Crestwood Holiday Rentals

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Holiday Rentals in Crestwood

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (632)
"The view was excellent "
The price is S$215
includes taxes & fees
2 Jan - 3 Jan,2025
Sentral Michigan Avenue
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, (344)
"Great stay "
Kasa Magnificent Mile Chicago
Sonder South Wabash
Living area

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (408)
"Outstanding accommodations! Will choose this property again for my travels."
The price is S$170
includes taxes & fees
28 Jan - 29 Jan,2025
Sonder South Wabash
Sonder Market Hall
Interior

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (231)
"Very nice place for the cost. Could hear outside and inside noises but noise doesn’t bother me. Would stay here again."
The price is S$104
includes taxes & fees
21 Jan - 22 Jan,2025
Sonder Market Hall
Level Chicago – Old Town
Front of property – evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (277)
"I loved the amenities available to us - garage parking, washer/dryer in unit, full kitchen and fully furnished. Staff were polite and helpful. Great location"
The price is S$309
includes taxes & fees
5 Jan - 6 Jan,2025
Level Chicago – Old Town
Sonder The Burnham Apartments
Marina

Sonder The Burnham Apartments

3.5 star property
9.0 out of 10, Wonderful, (124)
"Wonderful place with some personality "
The price is S$200
includes taxes & fees
27 Jan - 28 Jan,2025
Sonder The Burnham Apartments
Found Chicago powered by Sonder
Exterior

Found Chicago powered by Sonder

3.5 star property
7.6 out of 10, Good, (179)
"Excellent location, amazing price. No nonsense stay, you only get the basics here but very clean and simple. Pros: no carpet in rooms, no extra frilly pillows or curtains, all surfaces look like they can be easily wiped down and disinfected. You can actually open the windows. Self serve toiletry station. Coded locks instead of keys. Great location close to restaurants and bus stops. THE PRICE!!! Cons: non responsive staff in person and online, sometimes no staff at all. No view, stuffy room...
The price is S$192
includes taxes & fees
19 Jan - 20 Jan,2025
Found Chicago powered by Sonder
The Neighborhood Hotel-Little Italy
50-inch Smart TV with satellite channels

The Neighborhood Hotel-Little Italy

3.5 star property
9.6 out of 10, Exceptional, (113)
"Very nice, quiet and comfortable. As good or better than any 4 star hotel I've ever stayed at."
The Neighborhood Hotel-Little Italy
Kasa South Loop Chicago
42-inch Smart TV with digital channels, TV, streaming services

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (249)
"Everything was great from the beginning. From the instructions on where to park and enter to how to exit. "
Kasa South Loop Chicago
Kasa River North Chicago
Exterior

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (113)
"Very good location"
The price is S$200
includes taxes & fees
8 Jan - 9 Jan,2025
Kasa River North Chicago
Sonder Jewelers Row
Free toiletries, hair dryer, towels, soap

Sonder Jewelers Row

3.5 star property
8.2 out of 10, Very good, (136)
"Sonder check in experience as a first timer was super easy! Great instructions and no issues entering or exiting the property. Property was in great condition with all the amenities you could need. Only downside was the cigar bar downstairs... you could at certain times of day smell the cigar scent in our room upstairs. Not a huge issue, but if you were sensitive to the smell it would not be ideal."
The price is S$182
includes taxes & fees
13 Jan - 14 Jan,2025
Sonder Jewelers Row
Sonder The Plymouth
City view from property

Sonder The Plymouth

3.5 star property
8.4 out of 10, Very good, (87)
"Loved the location. "
The price is S$165
includes taxes & fees
23 Jan - 24 Jan,2025
Sonder The Plymouth
Sonder The Opal
Exterior

Sonder The Opal

3.5 star property
8.6 out of 10, Excellent, (28)
"We loved the location in River North with shops around plenty of nice restaurants. Walkable and good buses around. Apartment was very nice, we were 5 adults. A bit noisy because of bar nearby ( it depends of your tolerance to noise. Some of us were disturbed some heard nothing). We enjoyed our stay !"
The price is S$185
includes taxes & fees
21 Jan - 22 Jan,2025
Sonder The Opal
Sonder Greektown
40-inch flat-screen TV with digital channels, TV

Sonder Greektown

3.5 star property
9.0 out of 10, Wonderful, (36)
"The place was awesome, they had to kick out the people before me, so getting my room was a little bit late "
The price is S$201
includes taxes & fees
23 Jan - 24 Jan,2025
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, (11)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
Ground Floor Studios in Chicago by 747 Lofts
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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Other types of properties in Crestwood you may be interested in

Congress Plaza Hotel
Aerial view

Congress Plaza Hotel

3.5 star property
7.8 out of 10, Good, (8308)
"Loved the location and the history of the building. "
The price is S$148
includes taxes & fees
8 Jan - 9 Jan,2025
Congress Plaza Hotel
River Hotel
View from property

River Hotel

4.0 star property
8.8 out of 10, Excellent, (3650)
"This place was great for my family and I. The location was perfect for all the activities we planned. The service was great. When we asked for extra towels and coffee, they were delivered promptly. The only thing that was a bit of an inconvenience was that one of the elevators was out of service which caused a bit of a delay going to and from the lobby."
The price is S$148
includes taxes & fees
27 Jan - 28 Jan,2025
River Hotel
Hyatt Regency Chicago
2 bars/lounges

Hyatt Regency Chicago

4.0 star property
9.2 out of 10, Wonderful, (3125)
"Good location, close to Magnificent Mile , Milenium Park , dining."
The price is S$262
includes taxes & fees
10 Jan - 11 Jan,2025
Hyatt Regency Chicago
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.

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 Oak Hill Park. In the wider area, you’ll find Trinity Christian College and Gaelic Park.

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.