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Westchester Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Westchester vacation rentals

Exterior

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,283 reviews)
"Nice stay"
United States
Heather
The price is ₩209,206
₩286,192 total
includes taxes & fees
Sep 8 - Sep 9
Sentral Michigan Avenue
Lake

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.2 out of 10, Very Good, (20 reviews)
"Great location and super clean!"
United States
Erica
The price is ₩253,206
₩383,286 total
includes taxes & fees
Sep 9 - Sep 10
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, (520 reviews)
"We only stayed one night but we definitely want to go back and stay at least two nights. It really was beautiful, clean and very secure."
United States
Martha
The price is ₩334,572
₩426,840 total
includes taxes & fees
Sep 1 - Sep 2
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, (224 reviews)
"Great location and newly remodeled, clean rooms."
United States
Brian
The price is ₩223,822
₩256,235 total
includes taxes & fees
Aug 30 - Aug 31
The Gem Museum Suites
Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Exterior

5. 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 ₩264,774
₩456,543 total
includes taxes & fees
Sep 13 - Sep 14
Historic Oak Park Residence
Living area

6. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
8.2 out of 10, Very Good, (52 reviews)
"We had a great stay! Perfect location for cubs games and hanging out in wrigleyville."
United States
Kate
The price is ₩288,904
₩339,147 total
includes taxes & fees
Sep 8 - Sep 9
Wrigleyville Suites
Studio | Interior

7. 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 ₩125,980
₩234,610 total
includes taxes & fees
Sep 2 - Sep 3
Cabin 105 by 747 Lofts
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 ₩295,667
₩614,655 total
includes taxes & fees
Sep 7 - Sep 8
Classic Forest Park Foursquare < 1 Mi to Blue Line
Design Apartment, Private Bathroom (The Oak Park Loft) | Exterior

9. 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 price is ₩279,841
₩474,007 total
includes taxes & fees
Sep 16 - Sep 17
The Oak Park Loft
Studio | Exterior

10. 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 ₩265,340
₩536,041 total
includes taxes & fees
Aug 30 - Aug 31
Chicago Third Floor Studio by 747 Lofts
Interior

11. River West, Third Floor Chicago by 747 Lofts

River West, Third Floor Chicago by 747 Lofts
2.0 star property
West Town
8.8 out of 10, Excellent, (19 reviews)
"Loved the space and location "
United States
Caroline
The price is ₩255,669
₩394,370 total
includes taxes & fees
Aug 27 - Aug 28
River West, Third Floor Chicago by 747 Lofts
Studio | Living area

12. Ground Floor Studios in Chicago by 747 Lofts

Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
West Town
8.6 out of 10, Excellent, (25 reviews)
"It’s a really nice place. Its quite a distance from downtown Chicago. But it’s like 3 minutes from Chicago Blue line and a minute away from the bus station. Food is not a problem since there is a Korean grocery nearby. There is also a nearby Catholic church. The ameneties in this loft hotel is complete so if you are looking for a budget style trip and accommodation, I highly recommend this place."
United States
Joel
The price is ₩141,200
₩253,399 total
includes taxes & fees
Sep 9 - Sep 10
Ground Floor Studios in Chicago by 747 Lofts
Studio | Living area

13. 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, (15 reviews)
"i loved this place! would definitely come again"
United States
adrian
The price is ₩255,669
₩394,370 total
includes taxes & fees
Sep 24 - Sep 25
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
"Loved our stay"
Jaclyn 3-night trip
Posted 1 hour ago
Crowne Plaza Chicago West Loop by IHG

Find out more about Westchester

Search for Vacation rentals in Westchester on Expedia.co.uk! You can easily find your home rentals, villas, Vacation apartments in Westchester using one of the methods below:

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Look no further and take a look at our great range of rental properties in Westchester!

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.

How many vacation rentals are there in Westchester?

Expedia has 7 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.