Westchester Vacation Rentals

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Check prices for these dates

Tonight
Nov 19 - Nov 20
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Nov 20 - Nov 21
This weekend
Nov 21 - Nov 23
Next weekend
Nov 28 - Nov 30

Vacation Rentals in Westchester

Indoor pool
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

4.0 star property
9.2 out of 10, Wonderful, (986)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is P5,938
P8,700 total
includes taxes & fees
Dec 18 - Dec 19
Sentral Michigan Avenue
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago

Aparthotel in Downtown Chicago

4.0 star property
9.2 out of 10, Wonderful, (623)
"Room was very nice, location was wonderful."
United States
Nicholas
Kasa Magnificent Mile Chicago
Front of property - evening/night
Level Chicago – Old Town

Aparthotel in Downtown Chicago

4.0 star property
9.0 out of 10, Wonderful, (383)
"Property was clean, centrally located with wonderful staff. Will definitely stay again."
United States
Michelle
Level Chicago – Old Town
1 bedroom, individually decorated, individually furnished, desk
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Aparthotel in Downtown Chicago

3.5 star property
8.0 out of 10, Very Good, (402)
"Great location. Was there for the marathon and had a great stay. "
United States
HELGA
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Balcony
Kasa South Loop Chicago

Aparthotel in Downtown Chicago

4.0 star property
9.4 out of 10, Exceptional, (375)
"An excellent place to stay in Chicago downtown."
United States
ABDULHAFEEZ
Kasa South Loop Chicago
Lobby
Sonder by Marriott Bonvoy The Burnham Apartments Loop

Aparthotel in Downtown Chicago

3.5 star property
8.8 out of 10, Excellent, (254)
"Great stay. "
United States
Teresa
Sonder by Marriott Bonvoy The Burnham Apartments Loop
36-inch flat-screen TV with digital channels, TV
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Aparthotel in Near South Side

3.5 star property
8.6 out of 10, Excellent, (713)
"Love the unit and location close to multiple restaurants and shopping."
United States
Jessie
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
1 bedroom, individually furnished, desk, iron/ironing board
Sonder by Marriott Bonvoy The Opal Apartments River North

Aparthotel in Downtown Chicago

3.5 star property
8.4 out of 10, Very Good, (57)
"Worked great for a work and family trip."
United States
David
Sonder by Marriott Bonvoy The Opal Apartments River North
50-inch flat-screen TV with digital channels, TV
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Aparthotel in Downtown Chicago

3.5 star property
8.2 out of 10, Very Good, (188)
"Place was amazing! Very centralized, all sorts of restaurants nearby, and right next to the CTA Trains which is AWESOME!"
United States
Alexander
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Front of property
The Neighborhood Hotel-Little Italy

Aparthotel in Near West Side

4.0 star property
9.6 out of 10, Exceptional, (219)
"Staff was courteous. Great location."
United States
Pamela
The Neighborhood Hotel-Little Italy
Business center
Kasa River North Chicago

Aparthotel in Downtown Chicago

4.0 star property
9.4 out of 10, Exceptional, (179)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Living area
Wrigleyville Suites

Aparthotel in Lakeview

2.0 star property
9.6 out of 10, Exceptional, (25)
"Excellent location and very clean! Would stay again!"
United States
Jacob
The price is P4,561
P5,354 total
includes taxes & fees
Nov 20 - Nov 21
Wrigleyville Suites
Private kitchen
The Gem Museum Suites

Aparthotel in Downtown Evanston

3.5 star property
9.4 out of 10, Exceptional, (96)
"Great stay. The studio is small but has everything necessary."
United States
Julia
The price is P10,713
P12,264 total
includes taxes & fees
Nov 23 - Nov 24
The Gem Museum Suites
Living room
Sonder by Marriott Bonvoy Greektown Apartments

Aparthotel in Downtown Chicago

3.5 star property
8.6 out of 10, Excellent, (65)
"The kitchen had everything we needed, great space overall, safe location, clean, near everything we needed, access to bus and rail very close, we really enjoyed our stay. "
United States
Samuel
Sonder by Marriott Bonvoy Greektown Apartments
Free WiFi, bed sheets
Chicago luxury home suites

Aparthotel in Downtown Chicago

2.0 star property
10.0 out of 10, Exceptional, (1)
"This was Amazing stay I have ever had in my life. Wonderful host, super clean. Stunning views, close to everything that you would needed. "
New Zealand
Moha
The price is P17,678
P20,752 total
includes taxes & fees
Nov 20 - Nov 21
Chicago luxury home suites
Private kitchen
Stylish Apartment near Chicago Downtown

Aparthotel in Bridgeport

2.0 star property
The price is P14,673
P23,311 total
includes taxes & fees
Nov 20 - Nov 21
Stylish Apartment near Chicago Downtown
Interior
Art Villa

Aparthotel in West Town

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
United States
tomonobu
The price is P22,259
P47,342 total
includes taxes & fees
Nov 20 - Nov 21
Art Villa
Exterior
Ground Floor Studios in Chicago by 747 Lofts

Aparthotel in West Town

2.0 star property
9.0 out of 10, Wonderful, (21)
"The stay lacked in shelf space as well as other amenities that could be useful. "
United States
Zugeily
Ground Floor Studios in Chicago 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

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

10/10 Excellent
"Nice accommodation's and great area, mall And restaurants walking distance "
leticia 3-night trip
Posted 2 days ago
The Whitehall Hotel, BW Premier Collection

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 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 6 vacation rentals for your stay in Westchester.

What can I see and do in Westchester?

Explore the area and family-friendly sights such as Edge Ice Arena, or get out into nature at a spot like Millennium Park. You’ll find favorite places to visit like Wrigley Field and Michigan Avenue 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.