Westchester Holiday Rentals

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Check prices for these dates

Tonight
13 Nov - 14 Nov
Tomorrow
14 Nov - 15 Nov
This weekend
14 Nov - 16 Nov
Next weekend
21 Nov - 23 Nov

Holiday Rentals in Westchester

Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (983)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is S$219
includes taxes & fees
7 Dec - 8 Dec
Sentral Michigan Avenue
Private kitchen
4BR Corporate Suite Central and Modern

4BR Corporate Suite Central and Modern

2.0 star property
Near North Side
10.0 out of 10, Exceptional, (6)
"Great location in Lincoln Park. Easy walk to several shops and restaurants. And about a 5 minute walk to the redline station (North/Clybourn). Very clean and quiet inside the unit. Building is very new. Room access through the Latch app is simple. I would definitely stay here again. The overall experience was excellent and my other guests would agree. "
United States
Phillip
4BR Corporate Suite Central and Modern
Business centre
Kasa River North Chicago

Kasa River North Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (176)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Front of property – evening/night
Level Chicago – Old Town

Level Chicago – Old Town

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (378)
"Property was clean, centrally located with wonderful staff. Will definitely stay again."
United States
Michelle
Level Chicago – Old Town
Free WiFi
Chicago luxury home suites

Chicago luxury home suites

2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"This was Amazing stay I have ever had in my life. Wonderful host, super clean. Stunning views, close to everything that you would needed. "
New Zealand
Moha
The price is S$447
includes taxes & fees
17 Nov - 18 Nov
Chicago luxury home suites
Exterior
Chicago Third Floor Studio by 747 Lofts

Chicago Third Floor Studio by 747 Lofts

2.0 star property
West Town
9.6 out of 10, Exceptional, (5)
"Excellent facility with great amenities: laundry, kitchen and a great location close to the Loop and easy access to O’Hare airport via Blue Line or Kennedy Expressway."
United States
Philip
Chicago Third Floor Studio by 747 Lofts
Private kitchen
The Gem Museum Suites

The Gem Museum Suites

3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (95)
"Great stay. The studio is small but has everything necessary."
United States
Julia
The price is S$271
includes taxes & fees
18 Nov - 19 Nov
The Gem Museum Suites
Private kitchen
Stylish Apartment near Chicago Downtown

Stylish Apartment near Chicago Downtown

2.0 star property
Bridgeport
The price is S$505
includes taxes & fees
16 Nov - 17 Nov
Stylish Apartment near Chicago Downtown
Interior
Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line

3.0 star property
Forest Park
The price is S$501
includes taxes & fees
20 Nov - 21 Nov
Classic Forest Park Foursquare < 1 Mi to Blue Line
Interior
Art Villa

Art Villa

5.0 star property
West Town
10.0 out of 10, Exceptional, (2)
" "
United States
tomonobu
The price is S$858
includes taxes & fees
14 Dec - 15 Dec
Art Villa
View from property
The Oak Park Loft

The Oak Park Loft

2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is S$323
includes taxes & fees
16 Nov - 17 Nov
The Oak Park Loft
Living area
Wrigleyville Suites

Wrigleyville Suites

2.0 star property
Lakeview
9.6 out of 10, Exceptional, (25)
"Excellent location and very clean! Would stay again!"
United States
Jacob
The price is S$252
includes taxes & fees
14 Nov - 15 Nov
Wrigleyville Suites
Free WiFi
Logan Square SRO Hotel

Logan Square SRO Hotel

2.0 star property
Logan Square
The price is S$344
includes taxes & fees
15 Nov - 16 Nov
Logan Square SRO Hotel
Interior
Historic Oak Park Home

Historic Oak Park Home

2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
Historic Oak Park Home
Exterior
Ground Floor Studios in Chicago by 747 Lofts

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
West Town
9.0 out of 10, Wonderful, (21)
"This property is excellent!"
United States
Philip
The price is S$278
includes taxes & fees
16 Nov - 17 Nov
Ground Floor Studios in Chicago by 747 Lofts
Exterior
Historic Oak Park Residence

Historic Oak Park Residence

2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12)
"It was very spacious. The kids had a great time. I love having a washer and dryer to use due to having alot of kids"
United States
Makita
The price is S$375
includes taxes & fees
20 Nov - 21 Nov
Historic Oak Park Residence
Private kitchen
River West, Third Floor Chicago by 747 Lofts

River West, Third Floor Chicago by 747 Lofts

2.0 star property
West Town
9.0 out of 10, Wonderful, (17)
"Overall solid property, I will return."
United States
Fletcher
The price is S$182
includes taxes & fees
30 Nov - 1 Dec
River West, Third Floor Chicago by 747 Lofts
Private kitchen
Chicago Second Floor Studio by 747 Lofts

Chicago Second Floor Studio by 747 Lofts

2.0 star property
West Town
8.8 out of 10, Excellent, (13)
"Great location, convenient to downtown and blue line to airport. Everything necessary in unit, comfortable temperature and full kitchen with unique grocery store nearby."
United States
Barbara
The price is S$175
includes taxes & fees
1 Dec - 2 Dec
Chicago Second Floor Studio 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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Top Westchester Hotel Reviews

Eurostars Magnificent Mile

Eurostars Magnificent Mile

10/10 Excellent
"We loved our stay!! The views in the panoramic room were amazing!! Rooms were clean. Definitely coming back!! "
Italo 2-night trip
Posted 2 days ago
Eurostars Magnificent Mile

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 7 holiday rentals for your stay in Westchester.

What can I see and do in Westchester?

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