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Westchester Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Westchester holiday rentals

A modern living room with a sofa, a round coffee table, and a dining area with a table and chairs.

1. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (89 reviews)
"The bathroom was really clean. The beds were really comfortable"
United States
Jair
The price is S$307
includes taxes & fees
22 Nov - 23 Nov
Kasa Lake Shore Chicago
A modern building with the name 'SENIORAL' prominently displayed on the facade.

2. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,414 reviews)
"Great for extended stays."
United States
Jeff
The price is S$280
includes taxes & fees
12 Nov - 13 Nov
Sentral Michigan Avenue
A two-story house with a brick exterior, a sloped roof, and a front porch.

3. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (14 reviews)
"Great location with parking included"
United States
Melissa
The price is S$441
includes taxes & fees
12 Nov - 13 Nov
At Home in Oak Park
A modern bathroom with a built-in washer and dryer, a shower with a glass door, and a towel rack above the sink.

4. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (307 reviews)
"The rooms were clean, and the staff was courteous and the Breakfast was excellent."
United States
Ernest
The price is S$249
includes taxes & fees
19 Nov - 20 Nov
The Gem Museum Suites
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

5. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.6 out of 10, Exceptional, (50 reviews)
"The area was nice! Many restaurants and stores are at walking distance Room was very nice and clean"
United States
Francisco
The price is S$177
includes taxes & fees
30 Nov - 1 Dec
Wrigleyville Suites
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

6. 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 S$607
includes taxes & fees
16 Nov - 17 Nov
Classic Forest Park Foursquare < 1 Mi to Blue Line
A modern kitchen with a large island, bar stools, and a city view.

7. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (562 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
The price is S$307
includes taxes & fees
23 Nov - 24 Nov
Level Chicago – Old Town
A spacious living room with a grand piano, a comfortable sofa, and a dining area with a chandelier.

8. Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
8.8 out of 10, Excellent, (6 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
Historic Oak Park Home
A building with a white exterior and a tree with white blossoms in front.

9. 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
Historic Oak Park Residence
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

10/10 Excellent
"Excellent stay! Will definitely seek this property out again for my stay in Chicago"
Melissa 1-night trip
Posted less than an hour ago
The Chicago Hotel Collection Ambassador Gold Coast

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 Galloping Ghost, 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.