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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Westchester holiday rentals

A modern building with the name 'SENIORAL' prominently displayed on the facade.

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,400 reviews)
"10/10 2nd time staying here!"
United States
Rosa
The price is ฿4,567
฿5,361 total
includes taxes & fees
22 Nov - 23 Nov
Sentral Michigan Avenue
A modern kitchen with a large island, bar stools, and a city view.

2. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (557 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
The price is ฿5,837
฿7,685 total
includes taxes & fees
23 Nov - 24 Nov
Level Chicago – Old Town
A modern living room with a sofa, a round coffee table, and a dining area with a table and chairs.

3. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (81 reviews)
"Amazing property would stay here again. Looks exactly like pics!!"
United States
Felipe
The price is ฿6,046
฿9,196 total
includes taxes & fees
4 Nov - 5 Nov
Kasa Lake Shore Chicago
A spacious lobby with a high ceiling, a reception desk, comfortable seating, and a large stained glass window.

4. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (301 reviews)
"Good breakfast"
United States
Zhaohua
The price is ฿6,743
฿7,720 total
includes taxes & fees
8 Nov - 9 Nov
The Gem Museum Suites
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

5. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.0 out of 10, Wonderful, (50 reviews)
"What a gem right next to Wrigleyville Stadium! I had an emergency and needed somewhere to stay for two nights while my son was in the hospital. This was the perfect accommodation walkable to where I needed to go. Clean community townhome with lock off rooms, community kitchen and living room room – very lovely environment and excellent location. Walkable to many restaurants."
United States
Diana
The price is ฿4,195
฿4,925 total
includes taxes & fees
4 Nov - 5 Nov
Wrigleyville Suites
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

6. 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 ฿8,159
฿16,009 total
includes taxes & fees
4 Nov - 5 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

The Wade

The Wade

8/10 Good
"Very nice and comfortable"
Samantha 2-night trip
Posted 1 hour ago
The Wade

Find out more about Westchester

Search for holiday rentals in Westchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Westchester using one of the methods below:

  • View our selection of featured holiday rentals in Westchester
  • Use the map to find apartments and other holiday homes in the Westchester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Westchester while they last

Look no further and take a look at our great range of rental properties in Westchester!

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 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 Soldier 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.