Westchester Vacation Rentals

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Check prices for these dates

In two weeks
Apr 10 - Apr 12
In two months
May 22 - May 24
In three months
Jun 19 - Jun 21
In four months
Jul 17 - Jul 19

Our top choices for Westchester vacation rentals

Dining room

Aparthotel in Downtown Chicago

Kasa Magnificent Mile Chicago
4.0 star property
9.4 out of 10, Exceptional, (717 reviews)
"Fantastic location with great amenities and secure."
United States
Tomeka
Kasa Magnificent Mile Chicago
Indoor pool

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1,113 reviews)
"Clean spacious my go to vacation spot all year around "
United States
xavier
The price is NT$4,043
NT$5,683 total
includes taxes & fees
Apr 1 - Apr 2
Sentral Michigan Avenue
Full-size fridge, microwave, oven, stovetop

Aparthotel in Downtown Chicago

Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (449 reviews)
"Great value, friendly staff"
United States
Marcus
The price is NT$5,481
NT$7,222 total
includes taxes & fees
Mar 29 - Mar 30
Level Chicago – Old Town
Design Apartment, Private Bathroom (The Oak Park Loft) | 2 bedrooms

Apartment in Oak Park

The Oak Park Loft
2.0 star property
10.0 out of 10, Exceptional, (5 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is NT$4,136
NT$8,280 total
includes taxes & fees
Mar 30 - Mar 31
The Oak Park Loft
Lounge

Aparthotel in Downtown Chicago

Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (187 reviews)
"Nice area if you are renting a car, be aware that you would have to pay for street parking or go over a few blocks and park in a parking lot."
United States
Daysha
Kasa River North Chicago
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

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"Nice quiet hotel walking distance to a lot of the tourist hot spots. Hotel was nice, could use some cleaning. Hotel is magnificent. "
Heather 4-night trip
Posted 1 hour ago
Congress Plaza 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 9 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.