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Check prices for these dates

In two weeks
2 Jan - 4 Jan
In two months
13 Feb - 15 Feb
In three months
13 Mar - 15 Mar
In four months
10 Apr - 12 Apr

Our top choices for Westchester holiday rentals

Lounge
Kasa River North Chicago

Aparthotel in Downtown Chicago

Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (182)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Full-sized fridge, microwave, oven, stovetop
Level Chicago – Old Town

Aparthotel in Downtown Chicago

Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (401)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town
Indoor pool
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1011)
"This place made a great landing spot for a holiday weekend w family. Clean, great location, loved the holiday decorations and indoor pool / outside hot tub. Will stay again! "
United States
Deidre
The price is 3.110.181 ₫
4.423.485 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Sentral Michigan Avenue
Exterior
Chicago luxury home suites

Aparthotel in Downtown Chicago

Chicago luxury home suites
2.0 star property
7.4 out of 10, Good, (3)
"Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job."
Canada
pouya
The price is 3.553.740 ₫
4.171.736 ₫ total
includes taxes & fees
20 Dec - 21 Dec
Chicago luxury home suites
Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Exterior
Historic Oak Park Residence

Apartment in Oak Park

Historic Oak Park Residence
2.0 star property
9.6 out of 10, Exceptional, (12)
"Absolutely awesome "
United States
Erik
The price is 5.503.179 ₫
9.224.013 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Historic Oak Park Residence
Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Lounge
Historic Oak Park Home

Apartment in Oak Park

Historic Oak Park Home
2.0 star property
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
The price is 5.791.280 ₫
9.552.980 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Historic Oak Park Home
Studio | Interior
Cabin 105 by 747 Lofts

Aparthotel in West Town

Cabin 105 by 747 Lofts
2.0 star property
10.0 out of 10, Exceptional, (1)
The price is 1.586.284 ₫
3.564.269 ₫ total
includes taxes & fees
30 Dec - 31 Dec
Cabin 105 by 747 Lofts
Living area
Wrigleyville Suites

Aparthotel in Lakeview

Wrigleyville Suites
2.0 star property
9.6 out of 10, Exceptional, (26)
"Excellent location and very clean! Would stay again!"
United States
Jacob
The price is 3.222.058 ₫
3.782.375 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Wrigleyville Suites
Breakfast, lunch, dinner served; Greek cuisine
The Gem Museum Suites

Aparthotel in Downtown Evanston

The Gem Museum Suites
3.5 star property
9.4 out of 10, Exceptional, (98)
"Great stay. The studio is small but has everything necessary."
United States
Julia
The price is 4.785.703 ₫
5.478.673 ₫ total
includes taxes & fees
20 Dec - 21 Dec
The Gem Museum Suites
House (3 Bedrooms) | Interior
Classic Forest Park Foursquare < 1 Mi to Blue Line

Cottage in Forest Park

Classic Forest Park Foursquare < 1 Mi to Blue Line
3.0 star property
The price is 4.159.192 ₫
10.858.387 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Classic Forest Park Foursquare < 1 Mi to Blue Line
Design Apartment, Private Bathroom (The Oak Park Loft) | 2 bedrooms
The Oak Park Loft

Apartment in Oak Park

The Oak Park Loft
2.0 star property
10.0 out of 10, Exceptional, (5)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is 4.069.456 ₫
7.582.801 ₫ total
includes taxes & fees
21 Dec - 22 Dec
The Oak Park Loft
Interior
River West, Second Floor Chicago by 747 Lofts

Aparthotel in West Town

River West, Second Floor Chicago by 747 Lofts
2.0 star property
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 1.559.697 ₫
5.755.743 ₫ total
includes taxes & fees
23 Dec - 24 Dec
River West, Second Floor 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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Top Westchester Hotel Reviews

Swissotel - Chicago

Swissotel - Chicago

10/10 Excellent
"Wonderful. It’s just an overnight stay but the staff is exceptional "
Susan Ann 1-night trip
Posted 9 hours ago
Swissotel - Chicago

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 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.