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Westchester Vacation Rentals

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Westchester holiday rentals

Exterior

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,314 reviews)
"clean property, amazing staff, in-unit laundry machines, awesome location"
United States
Allison
The price is RM619
RM846 total
includes taxes & fees
21 Sept - 22 Sept
Sentral Michigan Avenue
Interior

2. Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
3.0 star property
Forest Park
The price is RM985
RM1,933 total
includes taxes & fees
22 Sept - 23 Sept
Classic Forest Park Foursquare < 1 Mi to Blue Line
Private kitchen

3. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (524 reviews)
"Location and facility was very nice"
United States
Brian
The price is RM1,240
RM1,556 total
includes taxes & fees
27 Sept - 28 Sept
Level Chicago – Old Town
Exterior

4. Historic Oak Park Residence

Historic Oak Park Residence
2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"The house is in an amazing neighborhood, easy access to subway, extremely clean and great follow-up and follow through communication with owner!"
United States
Ann-Marie
The price is RM979
RM1,572 total
includes taxes & fees
30 Sept - 1 Oct
Historic Oak Park Residence
Lake

5. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (29 reviews)
"Great location and super clean!"
United States
Erica
The price is RM794
RM1,186 total
includes taxes & fees
20 Sept - 21 Sept
Kasa Lake Shore Chicago
Restaurant

6. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (255 reviews)
"Really helpful staff, really nice rooms."
United States
Archita
The price is RM772
RM884 total
includes taxes & fees
28 Sept - 29 Sept
The Gem Museum Suites
Lounge

7. Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is RM890
RM1,471 total
includes taxes & fees
14 Oct - 15 Oct
Historic Oak Park Home
Living area

8. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
8.2 out of 10, Very good, (54 reviews)
"We had a great stay! Perfect location for cubs games and hanging out in wrigleyville."
United States
Kate
The price is RM978
RM1,148 total
includes taxes & fees
6 Oct - 7 Oct
Wrigleyville Suites
Lounge

9. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is RM816
RM1,386 total
includes taxes & fees
13 Oct - 14 Oct
At Home in Oak Park
Exterior

10. The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.2 out of 10, Wonderful, (7 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is RM723
RM1,280 total
includes taxes & fees
13 Oct - 14 Oct
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

River Hotel

River Hotel

10/10 Excellent
"Great staff easy to work with.and have good per and recomsations they were very pesonable"
David 1-night trip
Posted 2 hours ago
River Hotel

Find out more about Westchester

Search for holiday rentals in Westchester on Expedia.co.uk! 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 5 holiday rentals for your stay in Westchester.

What can I see and do in Westchester?

Explore the area and family-friendly sights such as Norridge Park District, or get out into nature at a spot like Millennium Park. You’ll find favourite places to visit such as Wrigley Field and Soldier Field 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.