Westchester Holiday Rentals

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Check prices for these dates

In two weeks
13 Feb - 15 Feb
In two months
27 Mar - 29 Mar
In three months
24 Apr - 26 Apr
In four months
22 May - 24 May

Our top choices for Westchester holiday rentals

Fireplace

King Bed, Game Room & Fire Pit | LCP Collection

King Bed, Game Room & Fire Pit | LCP Collection
Westchester
8.0 out of 10, Very good, (2 reviews)
"Great location, price and the place was well kept and accommodating."
United States
Carl M.
The price is HK$1,742
HK$3,996 total
includes taxes & fees
3 Feb - 4 Feb
King Bed, Game Room & Fire Pit | LCP Collection
TV, offices

Cozy Westchester Retreat Near Chicago & Parks

Cozy Westchester Retreat Near Chicago & Parks
Westchester
The price is HK$2,243
HK$6,903 total
includes taxes & fees
3 Feb - 4 Feb
Cozy Westchester Retreat Near Chicago & Parks
Fridge, microwave, oven, stovetop

Less is more! Pet friendly Tiny Home near Chicago!

Less is more! Pet friendly Tiny Home near Chicago!
Burr Ridge
9.8 out of 10, Exceptional, (37 reviews)
"We loved it! We were in for a short time and it was perfect!!"
United States
nicole l.
The price is HK$809
HK$1,643 total
includes taxes & fees
15 Feb - 16 Feb
Less is more! Pet friendly Tiny Home near Chicago!
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,066 reviews)
"Best full kitchen multi-room family lodging"
United States
Lee
The price is HK$857
HK$1,235 total
includes taxes & fees
3 Feb - 4 Feb
Sentral Michigan Avenue
Desk, iron/ironing board, travel cot, WiFi

Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is HK$524
HK$1,275 total
includes taxes & fees
3 Feb - 4 Feb
Chic Studio in the Heart of the Gold Coast
1 bedroom, WiFi, bed sheets

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is HK$539
HK$1,371 total
includes taxes & fees
4 Feb - 5 Feb
1BR Modern Luxe Apt with In-Unit Laundry
1 bedroom, iron/ironing board, travel cot, WiFi

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (7 reviews)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
The price is HK$539
HK$1,371 total
includes taxes & fees
3 Feb - 4 Feb
West Loop Living – Bright 1BR
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, (416 reviews)
"Clean, nice amenities and great staff."
United States
Sydnee
Level Chicago – Old Town
TV, offices

Complete 1BR Home Sum

Complete 1BR Home Sum
Downtown Chicago
The price is HK$539
HK$1,371 total
includes taxes & fees
4 Feb - 5 Feb
Complete 1BR Home Sum
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
Interior

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
The price is HK$945
HK$2,676 total
includes taxes & fees
19 Feb - 20 Feb
River North Rooftop With In and Out Parking 3
TV, offices

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
9.2 out of 10, Wonderful, (15 reviews)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is HK$539
HK$1,371 total
includes taxes & fees
3 Feb - 4 Feb
Modern Comfort: 1BR Unit w/ Laundry
TV, offices

Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is HK$539
HK$1,371 total
includes taxes & fees
8 Feb - 9 Feb
Sun-Drenched 1BR Apartment
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 HK$1,137
HK$1,335 total
includes taxes & fees
3 Feb - 4 Feb
Wrigleyville Suites
Fridge, microwave, oven, stovetop

Sleek 1BR Apt w/ Laundry

Sleek 1BR Apt w/ Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveller
The price is HK$539
HK$1,371 total
includes taxes & fees
8 Feb - 9 Feb
Sleek 1BR Apt w/ Laundry
Interior

2BR Chic & Comfortable Furnished Unit

2BR Chic & Comfortable Furnished Unit
Hermosa
10.0 out of 10, Exceptional, (4 reviews)
"Comfortable beds, great location"
United States
Jason
The price is HK$539
HK$1,489 total
includes taxes & fees
3 Feb - 4 Feb
2BR Chic & Comfortable Furnished Unit
Terrace/patio

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Uptown
10.0 out of 10, Exceptional, (49 reviews)
"It was perfect for a concert at the aragon ballroom, it was only a block away!"
United States
Maria G.
The price is HK$394
HK$1,838 total
includes taxes & fees
4 Feb - 5 Feb
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
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

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

10/10 Excellent
"Amazing staff, very friendly, clean, comfortable, amazing breakfast. "
Cathy 2-night trip
Posted 21 hours ago
Hotel Riu Plaza Chicago

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.

What are some of the best holiday rentals that Westchester has to offer?

HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony: This holiday home rental outside of Westchester is located in the city centre, and has a balcony, an arcade/games room and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Westchester?

Expedia has 8 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.