Westchester Holiday Rentals

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Check prices for these dates

In two weeks
17 Apr - 19 Apr
In two months
29 May - 31 May
In three months
26 Jun - 28 Jun
In four months
24 Jul - 26 Jul

Our top choices for Westchester holiday rentals

Room

McCormick Place Apartment-Hotel

McCormick Place Apartment-Hotel
3.5 star property
Near South Side
McCormick Place Apartment-Hotel
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,116 reviews)
"Clean spacious my go to vacation spot all year around "
United States
xavier
The price is S$216
includes taxes & fees
1 Apr - 2 Apr
Sentral Michigan Avenue
Full-sized fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (453 reviews)
"Staff was really nice"
United States
Anita
The price is S$324
includes taxes & fees
31 Mar - 1 Apr
Level Chicago – Old Town
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
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
The price is S$293
includes taxes & fees
12 Apr - 13 Apr
Kasa River North Chicago
Living area

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.2 out of 10, Wonderful, (30 reviews)
"Great location and space ! Will use again "
United States
Vanessa
The price is S$136
includes taxes & fees
31 Mar - 1 Apr
Wrigleyville Suites
Breakfast, lunch, dinner served; Greek cuisine

The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (108 reviews)
"This is a fantastic hotel with super friendly staff"
United States
German
The price is S$289
includes taxes & fees
26 Apr - 27 Apr
The Gem Museum Suites
Exterior

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is S$321
includes taxes & fees
31 Mar - 1 Apr
The Oak Park Loft
Lounge

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 S$341
includes taxes & fees
1 Apr - 2 Apr
Historic Oak Park Home
Exterior

Historic Oak Park Residence

Historic Oak Park Residence
2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"Absolutely awesome "
United States
Erik
The price is S$520
includes taxes & fees
1 Apr - 2 Apr
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

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"It’s older , yet has an amazing antique feel. Staff was more than helpful to find places to eat. It’s walkable to the 3 museums, weather permitting. It’s about 10 to 15 minute walk to the pear, about 7 to the Bean, and about 10 to the museums. Completely worth it! There are sidewalks everywhere, and walking paths that take you under traffic across the street. The air of Chicago was filled with the smell of weed. It’s everywhere. The room was clean, and comfortable. If you’re a little sleeper note it’s close to the train. This is a constant noise you could wake up to during the night. For a deep sleeper you should be fine. Parking in the city is separate from anywhere you will stay. Had to pay to enter into Chicago. There are paid time limits on all parking lots. Watch your times when parking your car. There is a parking area over by the museums as well, and down by the pear. The rides at the pear are fun . Recommend the wheel at night . It gives a great view of the city skyline. "
Kristen 1-night trip
Posted 1 hour ago
Congress Plaza Hotel

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 9 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 Michigan Avenue 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.