Search Holiday Rentals in Westchester

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
4 Dec - 5 Dec
Tomorrow
5 Dec - 6 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Holiday Rentals in Westchester

Indoor pool
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

4.0 star property
9.2 out of 10, Wonderful, (997)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is ฿3,215
฿4,710 total
includes taxes & fees
8 Dec - 9 Dec
Sentral Michigan Avenue
Front of property – evening/night
Level Chicago – Old Town

Aparthotel in Downtown Chicago

4.0 star property
9.0 out of 10, Wonderful, (392)
"Clean room cool staff enjoyed my stay will come stay again. "
United States
Donald
Level Chicago – Old Town
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago

Aparthotel in Downtown Chicago

4.0 star property
9.2 out of 10, Wonderful, (642)
"Clean facilities, great staff, good location "
United States
Emily
Kasa Magnificent Mile Chicago
Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Balcony
Kasa South Loop Chicago

Aparthotel in Downtown Chicago

4.0 star property
9.4 out of 10, Exceptional, (379)
"A very clean and spacious apartment with a great view. The parking garage right next to the building is very convenient. If the water pressure be improved, that will be perfect."
United States
Tammy
Kasa South Loop Chicago
Property entrance
The Neighborhood Hotel-Little Italy

Aparthotel in Near West Side

4.0 star property
9.6 out of 10, Exceptional, (221)
"Staff was courteous. Great location."
United States
Pamela
The Neighborhood Hotel-Little Italy
Free WiFi, bed sheets
Chicago luxury home suites

Aparthotel in Downtown Chicago

2.0 star property
10.0 out of 10, Exceptional, (2)
"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 ฿4,307
฿5,056 total
includes taxes & fees
7 Dec - 8 Dec
Chicago luxury home suites
Living area
Wrigleyville Suites

Aparthotel in Lakeview

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 ฿2,699
฿3,168 total
includes taxes & fees
9 Dec - 10 Dec
Wrigleyville Suites
Business centre
Kasa River North Chicago

Aparthotel in Downtown Chicago

4.0 star property
9.4 out of 10, Exceptional, (180)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Suite, 2 Bedrooms, Kitchen (Three Beds, Washer/Dryer) | Private kitchen | Full-sized fridge, microwave, stovetop, dishwasher
The Gem Museum Suites

Aparthotel in Downtown Evanston

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 ฿5,800
฿6,640 total
includes taxes & fees
5 Dec - 6 Dec
The Gem Museum Suites
Classic Apartment | Private kitchen
Stylish Apartment near Chicago Downtown

Aparthotel in Bridgeport

2.0 star property
The price is ฿7,944
฿12,621 total
includes taxes & fees
8 Dec - 9 Dec
Stylish Apartment near Chicago Downtown
Interior
Art Villa

Aparthotel in West Town

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
United States
tomonobu
Art Villa
Studio | Exterior
Ground Floor Studios in Chicago by 747 Lofts

Aparthotel in West Town

2.0 star property
9.0 out of 10, Wonderful, (21)
"The stay lacked in shelf space as well as other amenities that could be useful. "
United States
Zugeily
The price is ฿1,890
฿4,277 total
includes taxes & fees
10 Dec - 11 Dec
Ground Floor Studios in 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Westchester Hotel Reviews

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

10/10 Excellent
"Very kind staff, small but clean and comfortable room with a beautiful view! Great location, quiet. Checked all the boxes for my overnight trip!!"
Patrick 1-night trip
Posted 2 days ago
Club Quarters Hotel Wacker at Michigan, Chicago

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 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.