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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 ₩240,334
₩365,547 total
includes taxes & fees
Nov 15 - Nov 16
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)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is ₩257,346
₩443,719 total
includes taxes & fees
Oct 29 - Oct 30
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, (1,372 reviews)
"Perfect location to stay at if attending the bears games !"
United States
Jacob
The price is ₩192,425
₩225,887 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, (287 reviews)
"Really helpful staff, really nice rooms."
United States
Archita
The price is ₩309,063
₩353,816 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 ₩376,210
₩474,774 total
includes taxes & fees
Nov 3 - Nov 4
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 ₩238,368
₩422,099 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

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"Our room was large and spacious as requested. Everything was clean and cozy. The staff was pleasant and very helpful. The hotel was overall in great shape considering its age , location and continual use. The only issue was for Chi marathon weekend only one elevator was working which caused a huge issue trying to go up to your room or down to the lobby. At one point I waited over 10 minutes to get down to the lobby from the 7th floor. That was a hassle."
Judith 2-night trip
Posted less than an hour ago
Congress Plaza Hotel

Find out more about Westchester

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

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