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Check prices for these dates

In two weeks
27 Feb - 1 Mar
In two months
10 Apr - 12 Apr
In three months
8 May - 10 May
In four months
5 Jun - 7 Jun

Our top choices for Westchester holiday rentals

Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,071 reviews)
"Best full kitchen multi-room family lodging"
United States
Lee
The price is 2.841.800 ₫
4.096.531 ₫ total
includes taxes & fees
24 Feb - 25 Feb
Sentral Michigan Avenue
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (183 reviews)
"Awesome stay "
United States
Sally
Kasa River North Chicago
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, (425 reviews)
"Clean, nice amenities and great staff."
United States
Sydnee
The price is 5.019.747 ₫
6.533.261 ₫ total
includes taxes & fees
11 Feb - 12 Feb
Level Chicago – Old Town
Living area

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.2 out of 10, Wonderful, (29 reviews)
"Nice place "
United States
Barry
The price is 3.078.702 ₫
3.614.087 ₫ total
includes taxes & fees
16 Feb - 17 Feb
Wrigleyville Suites
Interior

Chicago Third Floor Studio by 747 Lofts

Chicago Third Floor Studio by 747 Lofts
2.0 star property
West Town
9.8 out of 10, Exceptional, (7 reviews)
"Clean, easy to check in, all the household items you’d expect"
United States
Jason
The price is 1.770.881 ₫
8.791.289 ₫ total
includes taxes & fees
15 Feb - 16 Feb
Chicago Third Floor Studio by 747 Lofts
Apartment, Private Bathroom | Lounge

At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.4 out of 10, Exceptional, (9 reviews)
"Great location in Oak Park- walkable, wondering area for restaurants and strolling through the beautiful neighborhoods."
United States
Kathryn
The price is 3.166.295 ₫
6.502.592 ₫ total
includes taxes & fees
24 Feb - 25 Feb
At Home in Oak Park
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, (104 reviews)
"This is a fantastic hotel with super friendly staff"
United States
German
The price is 4.711.347 ₫
5.393.689 ₫ total
includes taxes & fees
16 Feb - 17 Feb
The Gem Museum Suites
Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Lounge

Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"Wanted a house in oak park and this was such a pleasant, comfortable and convenient place. Really comfortable beds too. Even a lovely piano. "
United States
judith
The price is 3.106.690 ₫
6.434.694 ₫ total
includes taxes & fees
24 Feb - 25 Feb
Historic Oak Park Home
Dining room

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (691 reviews)
"Perfect location and very clean! "
United States
Latoya
Kasa Magnificent Mile Chicago
Interior

River West, Third Floor Chicago by 747 Lofts

River West, Third Floor Chicago by 747 Lofts
2.0 star property
West Town
9.0 out of 10, Wonderful, (17 reviews)
"Loved the space and location "
United States
Caroline
The price is 3.074.115 ₫
7.557.985 ₫ total
includes taxes & fees
13 Feb - 14 Feb
River West, Third Floor Chicago by 747 Lofts
Exclusive Room, Private Bathroom, Garden View (2nd Floor) | 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 3.115.920 ₫
6.450.474 ₫ total
includes taxes & fees
11 Feb - 12 Feb
Historic Oak Park Residence
Exterior

Ground Floor Studios in Chicago by 747 Lofts

Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
West Town
9.0 out of 10, Wonderful, (21 reviews)
"The stay lacked in shelf space as well as other amenities that could be useful. "
United States
Zugeily
The price is 1.677.663 ₫
5.148.222 ₫ total
includes taxes & fees
12 Feb - 13 Feb
Ground Floor Studios in Chicago by 747 Lofts
Design Apartment, Private Bathroom (The Oak Park Loft) | 2 bedrooms

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 2.902.479 ₫
6.206.133 ₫ total
includes taxes & fees
11 Feb - 12 Feb
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

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

10/10 Excellent
"Great location"
Wei 1-night trip
Posted 1 day ago
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

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.