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Check prices for these dates

Tonight
18 Nov - 19 Nov
Tomorrow
19 Nov - 20 Nov
This weekend
21 Nov - 23 Nov
Next weekend
28 Nov - 30 Nov

Top Holiday Rentals in Westchester

Business centre
Kasa River North Chicago

Kasa River North Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (179)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Free WiFi, bed sheets
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 7.642.370 ₫
8.971.377 ₫ total
includes taxes & fees
19 Nov - 20 Nov
Chicago luxury home suites
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, (383)
"Property was clean, centrally located with wonderful staff. Will definitely stay again."
United States
Michelle
Level Chicago – Old Town
Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (986)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is 2.655.592 ₫
3.890.757 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Sentral Michigan Avenue
Studio | Private kitchen | Fridge, oven, coffee/tea maker, toaster
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 1.694.761 ₫
3.710.502 ₫ total
includes taxes & fees
30 Nov - 1 Dec
River West, Third Floor Chicago by 747 Lofts
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 2.039.722 ₫
2.394.430 ₫ total
includes taxes & fees
19 Nov - 20 Nov
Wrigleyville Suites
Classic Apartment | Private kitchen
Stylish Apartment near Chicago Downtown

Stylish Apartment near Chicago Downtown

2.0 star property
Bridgeport
The price is 6.561.150 ₫
10.424.173 ₫ total
includes taxes & fees
19 Nov - 20 Nov
Stylish Apartment near Chicago Downtown
Interior
Art Villa

Art Villa

5.0 star property
West Town
10.0 out of 10, Exceptional, (2)
" "
United States
tomonobu
The price is 7.283.238 ₫
17.393.859 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Art Villa
Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Exterior
Historic Oak Park Residence

Historic Oak Park Residence

2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12)
"Absolutely awesome "
United States
Erik
The price is 4.075.755 ₫
7.592.299 ₫ total
includes taxes & fees
20 Nov - 21 Nov
Historic Oak Park Residence
Apartment (4 Bedrooms) | Interior
Walk to Wrigley Field! Townhouse w/ Pool Table

Walk to Wrigley Field! Townhouse w/ Pool Table

3.0 star property
Lakeview
The price is 5.692.248 ₫
15.813.381 ₫ total
includes taxes & fees
20 Nov - 21 Nov
Walk to Wrigley Field! Townhouse w/ Pool Table
Room, 1 Queen Bed, Non Smoking | Free WiFi
Logan Square SRO Hotel

Logan Square SRO Hotel

2.0 star property
Logan Square
The price is 4.743.000 ₫
7.544.058 ₫ total
includes taxes & fees
10 Dec - 11 Dec
Logan Square SRO Hotel
Suite, 2 Bedrooms, Kitchen (Three Beds, Washer/Dryer) | Private kitchen | Full-sized fridge, microwave, stovetop, dishwasher
The Gem Museum Suites

The Gem Museum Suites

3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (96)
"Great stay. The studio is small but has everything necessary."
United States
Julia
The price is 4.790.430 ₫
5.484.226 ₫ total
includes taxes & fees
30 Nov - 1 Dec
The Gem Museum Suites
Studio | 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)
"Cute little studio that was clean. There was a nice size kitchen and was close to our activities in the West loop of Chicago. There was also assistance with parking located in the lofts."
United States
Jennifer
The price is 1.747.994 ₫
6.011.909 ₫ total
includes taxes & fees
20 Nov - 21 Nov
Chicago Third Floor Studio by 747 Lofts
Studio | Exterior
River West, Second Floor Chicago by 747 Lofts

River West, Second Floor Chicago by 747 Lofts

2.0 star property
West Town
9.6 out of 10, Exceptional, (4)
"I need to somewhere to stay for a night in Chicago and found this place. It had a varying level of reviews but found the property more the suitable for what I paid. Easy to follow instructions to get in, clean, and convienent. They even provide ear plugs to drown out the sounds of the city."
United States
Anonymous traveller
The price is 1.747.994 ₫
6.011.909 ₫ total
includes taxes & fees
20 Nov - 21 Nov
River West, Second Floor Chicago by 747 Lofts
Studio | Private kitchen | Fridge, oven, coffee/tea maker, toaster
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 1.534.799 ₫
3.496.780 ₫ total
includes taxes & fees
1 Dec - 2 Dec
Chicago Second Floor Studio by 747 Lofts
House (3 Bedrooms) | 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 4.585.422 ₫
10.150.385 ₫ total
includes taxes & fees
20 Nov - 21 Nov
Classic Forest Park Foursquare < 1 Mi to Blue Line
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
"Loved the room! Clean, cozy, beautiful view!"
ZsaNay 1-night trip
Posted 16 hours 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 6 holiday rentals for your stay in Westchester.

What can I see and do in Westchester?

Explore the area and family-friendly sights such as Edge Ice Arena, 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.