Westchester Holiday Rentals

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Check prices for these dates

Tonight
20 Jan - 21 Jan
Tomorrow
21 Jan - 22 Jan
This weekend
24 Jan - 26 Jan
Next weekend
31 Jan - 2 Feb

Holiday Rentals in Westchester

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (658)
"Everything was amazing I forgot the two ladies that helped if I’m not mistaken one was Sandra they were great "
The price is S$216
includes taxes & fees
21 Jan - 22 Jan
Sentral Michigan Avenue
Sonder South Wabash
Living area

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (418)
"I liked it a lot. The only detail that is important to me is the blackout on the windows, it let in a lot of light in the morning. For those who like to sleep in the dark, this is important. But there is nothing to criticize. We liked it a lot, we will definitely come back."
The price is S$176
includes taxes & fees
10 Feb - 11 Feb
Sonder South Wabash
Sonder Market Hall
Interior

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (242)
"New. Modern. Cozy.Clean & quiet place. Will book it again!"
The price is S$101
includes taxes & fees
10 Feb - 11 Feb
Sonder Market Hall
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, (353)
"Great property. Quick check in and in great location. Will definitely come back "
Kasa Magnificent Mile Chicago
Sonder The Burnham Apartments
Marina

Sonder The Burnham Apartments

3.5 star property
8.8 out of 10, Excellent, (132)
"If you are a walker and just want to explore what Chicago has to offer please book this place. You can store your bags before and after checkin/out and the lobby is so nice and quiet. "
The price is S$202
includes taxes & fees
23 Jan - 24 Jan
Sonder The Burnham Apartments
Level Chicago – Old Town
Front of property – evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (283)
"The lady in the front was amazing and very helpful."
The price is S$298
includes taxes & fees
21 Jan - 22 Jan
Level Chicago – Old Town
Found Chicago powered by Sonder
Exterior

Found Chicago powered by Sonder

3.5 star property
7.6 out of 10, Good, (180)
"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$194
includes taxes & fees
11 Feb - 12 Feb
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, (120)
"Unique, modern rooms"
The Neighborhood Hotel-Little Italy
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$165
includes taxes & fees
10 Feb - 11 Feb
Sonder Jewelers Row
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, (251)
"It was great. Place was clean. Stocked with essentials. Great place to be. Would definitely stay here again"
Kasa South Loop Chicago
Kasa River North Chicago
Exterior

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (117)
"Great"
The price is S$140
includes taxes & fees
26 Jan - 27 Jan
Kasa River North Chicago
Sonder The Plymouth
City view from property

Sonder The Plymouth

3.5 star property
8.4 out of 10, Very good, (88)
"Loved the location. "
The price is S$185
includes taxes & fees
23 Jan - 24 Jan
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$175
includes taxes & fees
21 Jan - 22 Jan
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$259
includes taxes & fees
23 Jan - 24 Jan
Sonder Greektown
Ground Floor Studios in Chicago by 747 Lofts
Exterior

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.6 out of 10, Exceptional, (12)
"Overall for solo travel is recommended."
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 Westchester you may be interested in

Congress Plaza Hotel
Aerial view

Congress Plaza Hotel

3.5 star property
7.8 out of 10, Good, (8422)
"My room didn’t have a remote and they never brought it. The bathroom could have been remodeled or something, the tub was old but other than that pretty decent"
The price is S$149
includes taxes & fees
21 Jan - 22 Jan
Congress Plaza Hotel
River Hotel
View from property

River Hotel

4.0 star property
8.8 out of 10, Excellent, (3725)
"I enjoyed my stay no complaints ☺️"
The price is S$141
includes taxes & fees
26 Jan - 27 Jan
River Hotel
Eurostars Magnificent Mile
Lobby lounge

Eurostars Magnificent Mile

4.0 star property
8.6 out of 10, Excellent, (2816)
"Staycation was very nice. Spa is the absolute best! Service and Ambiance was perfect."
The price is S$150
includes taxes & fees
18 Feb - 19 Feb
Eurostars Magnificent Mile
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 holiday rentals in Westchester?

Yes, there are holiday rentals close to the most popular sights in Westchester, 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 Westchester. Make sure you have time to check out the basketball games while you're in the area.

How many holiday rentals are there in Westchester?

Expedia has 5 holiday rentals for your stay in Westchester.

What can I see and do in Westchester?

Explore the area and family-friendly sights such as Parkway Bank Park Entertainment District, or get out into nature at a spot like Millennium Park. You’ll find favourite places to visit such as Michigan Avenue and Wrigley Field in the wider area.

What are holiday rentals like in Westchester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Westchester. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for family trips.