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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sep - 13 Sep
In four months
9 Oct - 11 Oct

Our top choices for Westchester holiday rentals

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 ฿3,677
฿9,631 total
includes taxes & fees
17 Jun - 18 Jun
Chicago Third Floor Studio by 747 Lofts
Breakfast, lunch and dinner served

The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (136 reviews)
"Perfect place to stay!"
United States
Anton
The price is ฿4,951
฿5,668 total
includes taxes & fees
17 Jun - 18 Jun
The Gem Museum Suites
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,191 reviews)
"Great location"
United States
JAVIER
The price is ฿5,783
฿7,744 total
includes taxes & fees
1 Jul - 2 Jul
Sentral Michigan Avenue
Design Apartment, Private Bathroom (The Oak Park Loft) | Exterior

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (6 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is ฿5,781
฿10,233 total
includes taxes & fees
30 Jun - 1 Jul
The Oak Park Loft
Living area

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.0 out of 10, Wonderful, (38 reviews)
"Amazing !!!!! Would stay again, clean, beautiful Spot, great area !"
United States
Luka
The price is ฿7,383
฿8,667 total
includes taxes & fees
17 Jun - 18 Jun
Wrigleyville Suites
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, (493 reviews)
"Very clean and loved the location and amenities with the store on the first floor was fantastic"
United States
Kimberly
The price is ฿8,174
฿10,399 total
includes taxes & fees
29 Jun - 30 Jun
Level Chicago – Old Town
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)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is ฿5,863
฿10,346 total
includes taxes & fees
28 Jun - 29 Jun
Historic Oak Park Home
Studio | Interior

Cabin 105 by 747 Lofts

Cabin 105 by 747 Lofts
2.0 star property
West Town
6.0 out of 10, (2 reviews)
"The code that was provided was incorrect. I was so anxious waiting outside the building until I was lucky that other guests were out and helped me get in. I tried reaching the “24/7” line but no response until a while and they had to reset everything before I was able to get in. First and last time I will be staying here. The bed is so small for even one person and the bathroom lights felt like a ghost was there. Do not book here, your anxiety will be through the roof !"
United States
Jamila
The price is ฿3,340
฿6,049 total
includes taxes & fees
18 Jun - 19 Jun
Cabin 105 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)
"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 ฿8,371
฿13,218 total
includes taxes & fees
22 Jun - 23 Jun
Historic Oak Park Residence
Studio | Living area

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, (22 reviews)
"Great area and surprisingly nice room!"
United States
Michael
The price is ฿3,913
฿6,756 total
includes taxes & fees
29 Jun - 30 Jun
Ground Floor Studios in Chicago by 747 Lofts
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, (18 reviews)
"Cvs. Dunkin Donuts. Pizza pie all 1-2 blocks walking distance "
United States
Paul
The price is ฿3,677
฿9,631 total
includes taxes & fees
17 Jun - 18 Jun
River West, Third Floor Chicago by 747 Lofts
Studio | Living area

Chicago Second Floor Studio by 747 Lofts

Chicago Second Floor Studio by 747 Lofts
2.0 star property
West Town
9.0 out of 10, Wonderful, (14 reviews)
"i loved this place! would definitely come again"
United States
adrian
The price is ฿5,568
฿8,785 total
includes taxes & fees
21 Jun - 22 Jun
Chicago Second Floor Studio by 747 Lofts
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

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

8/10 Good
"Location in West Loop is fantastic, a block away from Whole Foods and a number of great restaurants in Greek town. The staff was fantastic in addressing our needs immediately including a clogged sink and sliding door that came off the tracks. The infrastructure is a bit old and outdated. The only complaint was that we had requested a crib, which the check-in staff had reassured us would be in our room. However, it was not there when we arrived. We called to ask for one to be brought up, which took about 20 minutes. Normally, it would not be a big deal, but we arrived at 11 PM, so it was less than ideal for our toddler as it was very much past his bedtime."
Rainy 4-night trip
Posted 5 hours ago
Crowne Plaza Chicago West Loop by IHG

Find out more about Westchester

Search for holiday rentals in Westchester on Expedia! 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 10 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.