Westchester Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Westchester

Indoor pool
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

4.0 star property
9.2 out of 10, Wonderful, (998)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is NT$3,691
NT$5,249 total
includes taxes & fees
Dec 21 - Dec 22
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, (393)
"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, (381)
"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 NT$4,217
NT$4,951 total
includes taxes & fees
Dec 7 - Dec 8
Chicago luxury home suites
Business center
Kasa River North Chicago

Aparthotel in Downtown Chicago

4.0 star property
9.6 out of 10, Exceptional, (181)
"Awesome stay "
United States
Sally
Kasa River North Chicago
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 NT$2,474
NT$2,904 total
includes taxes & fees
Dec 7 - Dec 8
Wrigleyville Suites
Suite, 2 Bedrooms, Kitchen (Three Beds, Washer/Dryer) | Private kitchen | Full-size 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 NT$5,679
NT$6,502 total
includes taxes & fees
Dec 7 - Dec 8
The Gem Museum Suites
Classic Apartment | Private kitchen
Stylish Apartment near Chicago Downtown

Aparthotel in Bridgeport

2.0 star property
The price is NT$7,779
NT$12,358 total
includes taxes & fees
Dec 14 - Dec 15
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 NT$1,851
NT$4,188 total
includes taxes & fees
Dec 10 - Dec 11
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.
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Top Westchester Hotel Reviews

River Hotel

River Hotel

10/10 Excellent
"Close and convenient to everything! Great view from the room :)"
Lasya 2-night trip
Posted 19 hours ago
River Hotel

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 vacation rentals in Westchester?

Yes, you can find vacation rentals close to popular points of interest in Westchester, or you can select a secluded option if you want a relaxing place to 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 vacation rentals are there in Westchester?

Expedia has 6 vacation 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 favorite places to visit like Wrigley Field and Michigan Avenue in the larger area.

What are vacation rentals like in Westchester?

Vacation rentals are privately owned accommodations you can book for a few days or a quick weekend in Westchester. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll feel right at home. If you're concerned about a clean environment, a vacation rental can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for a small group gathering.