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Westchester Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Westchester vacation rentals

Lake

1. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (68 reviews)
"First time staying there and we absolutely loved our stay. We will definitely be going back."
United States
Iliana
The price is NT$5,758
NT$8,758 total
includes taxes & fees
Nov 1 - Nov 2
Kasa Lake Shore Chicago
Terrace/patio

2. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (13 reviews)
"The apartment was clean and had everything we needed for a comfortable stay. Highly recommended!"
Italy
Marco
The price is NT$6,851
NT$11,415 total
includes taxes & fees
Oct 26 - Oct 27
At Home in Oak Park
A modern building with the name 'SENIORAL' prominently displayed on the facade.

3. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,374 reviews)
"Perfect location to stay at if attending the bears games !"
United States
Jacob
The price is NT$4,607
NT$5,408 total
includes taxes & fees
Nov 9 - Nov 10
Sentral Michigan Avenue
A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

4. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (288 reviews)
"Very charming hotel we really enjoyed having breakfast in the morning and ability to have a bottle of wine with dinner at Knight and our bag was very comfortable and nice having the ability to open the window and have some fresh air all in all very charming"
United States
Kathleen
The price is NT$7,367
NT$8,433 total
includes taxes & fees
Nov 12 - Nov 13
The Gem Museum Suites
A modern kitchen with a large island, bar stools, and a city view.

5. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (541 reviews)
"Great location, very clean, loved the gym and cafe!"
United States
Kerry
The price is NT$9,006
NT$11,366 total
includes taxes & fees
Nov 2 - Nov 3
Level Chicago – Old Town
A modern building with large glass windows, surrounded by a grassy area with trees and a pathway.

6. The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.4 out of 10, Exceptional, (8 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is NT$5,749
NT$10,179 total
includes taxes & fees
Oct 27 - Oct 28
The Oak Park Loft
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 Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good
"Room smelled so clean and fresh! Our room size was perfect for our stay. Staff was super nice and helped a lot. I did wish a microwave was available in the room. Location was great - nearby stores, cafes and a good bagel spot. Neighborhood was safe and secure. Would recommend the hotel for future stays."
Kanae 2-night trip
Posted 1 hour ago
The Chicago Hotel Collection Ambassador Gold Coast

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 5 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 Soldier Field 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.