Westchester Holiday Rentals

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Check prices for these dates

In two weeks
16 Jan - 18 Jan
In two months
27 Feb - 1 Mar
In three months
27 Mar - 29 Mar
In four months
24 Apr - 26 Apr

Our top choices for Westchester holiday rentals

Private kitchen
ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments
2.0 star property
10.0 out of 10, Exceptional, (8)
"We loved at our stay at this property. It was one of the best stays we have had on vacation."
United States
Javeria
The price is S$859
includes taxes & fees
30 Dec - 31 Dec
ENVITAE Hotel 4 Bedroom Luxury Apartments
Indoor pool
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1026)
"My favorite place to stay hands-down"
United States
Michele
The price is S$216
includes taxes & fees
4 Jan - 5 Jan, 2026
Sentral Michigan Avenue
Business centre
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
Front of property – evening/night
Level Chicago – Old Town

Aparthotel in Downtown Chicago

Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (406)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town
Front of property
Chicago luxury home suites

Aparthotel in Downtown Chicago

Chicago luxury home suites
2.0 star property
10.0 out of 10, Exceptional, (4)
"Amazing stay! The location is very central and close to everything. The room was spotless, and the mattress was very comfortable. I really appreciated that the property is pet friendly. I was able to bring my dog along, which made the trip even better. The view was absolutely stunning. The hosts were very responsive and helpful throughout our stay. Highly recommend!"
Canada
Alex
The price is S$198
includes taxes & fees
30 Dec - 31 Dec
Chicago luxury home suites
Exterior
Chicago Third Floor Studio by 747 Lofts

Aparthotel in West Town

Chicago Third Floor Studio by 747 Lofts
2.0 star property
9.8 out of 10, Exceptional, (6)
"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 S$289
includes taxes & fees
30 Dec - 31 Dec
Chicago Third 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

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"When I pulled up I was wholeheartedly greeted by the doorman. Upon entering the hotel it was a joyful and friendly atmosphere. The receptionist was very courteous and professional. I’ve stayed here multiply times and have been very satisfied. Will return again. One more thing, the hotel is in a great location."
Margo 3-night trip
Posted 1 day ago
The Royal Sonesta Chicago Downtown

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.