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Westchester Vacation Rentals

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Check prices for these dates

In two weeks
25 Sep - 27 Sep
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Westchester vacation rentals

Exterior

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,310 reviews)
"clean property, amazing staff, in-unit laundry machines, awesome location"
United States
Allison
The price is SAR 635
SAR 856 total
includes taxes & fees
21 Sep - 22 Sep
Sentral Michigan Avenue
Lake

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (26 reviews)
"Great location and super clean!"
United States
Erica
The price is SAR 732
SAR 1,094 total
includes taxes & fees
20 Sep - 21 Sep
Kasa Lake Shore Chicago
Full-size fridge, microwave, oven, stovetop

3. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (523 reviews)
"Location and facility was very nice"
United States
Brian
The price is SAR 1,137
SAR 1,428 total
includes taxes & fees
27 Sep - 28 Sep
Level Chicago – Old Town
Breakfast, lunch and dinner served

4. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (253 reviews)
"Really helpful staff, really nice rooms."
United States
Archita
The price is SAR 693
SAR 793 total
includes taxes & fees
28 Sep - 29 Sep
The Gem Museum Suites
Apartment, Private Bathroom | Lounge

5. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is SAR 854
SAR 1,395 total
includes taxes & fees
21 Sep - 22 Sep
At Home in Oak Park
Living area

6. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
8.2 out of 10, Very Good, (54 reviews)
"We had a great stay! Perfect location for cubs games and hanging out in wrigleyville."
United States
Kate
The price is SAR 899
SAR 1,055 total
includes taxes & fees
6 Oct - 7 Oct
Wrigleyville Suites
Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Lounge

7. 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 SAR 1,092
SAR 1,667 total
includes taxes & fees
27 Sep - 28 Sep
Historic Oak Park Home
House (3 Bedrooms) | Interior

8. 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 SAR 909
SAR 1,783 total
includes taxes & fees
27 Sep - 28 Sep
Classic Forest Park Foursquare < 1 Mi to Blue Line
Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Exterior

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
The price is SAR 903
SAR 1,451 total
includes taxes & fees
30 Sep - 1 Oct
Historic Oak Park Residence
Design Apartment, Private Bathroom (The Oak Park Loft) | Exterior

10. The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.2 out of 10, Wonderful, (7 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
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

Hilton Chicago

Hilton Chicago

10/10 Excellent
"My stay at the Chicago Hilton was truly exceptional. From the moment I arrived, I was impressed by the beautiful and elegant surroundings, outstanding amenities, and impeccable service. The staff were gracious, attentive, and professional, making the entire experience feel warm and welcoming. The hotel itself is absolutely gorgeous, with amenities that exceeded my expectations. I look forward to staying here again and would highly recommend the Chicago Hilton to anyone seeking a memorable and luxurious experience in Chicago."
Emelita 2-night trip
Posted 1 hour ago
Hilton Chicago

Frequently asked questions

Can I find vacation rentals in Westchester?

Yes, you can find vacation rentals close to popular points of interest in Westchester, or you can select a secluded option if you want a relaxing place to 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 vacation rentals that Westchester has to offer?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This vacation home rental outside of Westchester is located in the city center and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Westchester?

Expedia has 5 vacation 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 favorite places to visit like Wrigley Field and Soldier Field in the larger area.

What are vacation rentals like in Westchester?

Vacation rentals are privately owned accommodations you can book for a few days or a quick weekend in Westchester. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll feel right at home. If you're concerned about a clean environment, a vacation rental can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for a small group gathering.