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Westchester Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Westchester vacation rentals

A modern kitchen with stainless steel appliances, wooden cabinets, and a tiled backsplash.

1. PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Westchester
9.6 out of 10, Exceptional, (24 reviews)
"Great place Great location "
United States
Josh W.
The price is ￥30,982
￥70,480 total
includes taxes & fees
Oct 14 - Oct 15
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
A bedroom with a bed, a bench, a window, and a wall-mounted shelf.

2. Near Brookfield Zoo - King Bed - Sleeps 6

Near Brookfield Zoo - King Bed - Sleeps 6
Westchester
8.0 out of 10, Very good, (2 reviews)
"Great location for what we were needing for our trip. Very clean!"
United States
Brandi B.
The price is ￥21,099
￥42,737 total
includes taxes & fees
Oct 27 - Oct 28
Near Brookfield Zoo - King Bed - Sleeps 6
A spacious bedroom with a large bed, a desk, and a chair.

3. Westchester House | Sleeps 10 | Near Chicago & Parks | Close to Restaurants & Easy Local Transport Access | Long private driveway

Westchester House | Sleeps 10 | Near Chicago & Parks | Close to Restaurants & Easy Local Transport Access | Long private driveway
Westchester
10.0 out of 10, Exceptional, (1 review)
"Cute house with easy access to shopping and interstate"
United States
Jenny W.
The price is ￥57,904
￥131,010 total
includes taxes & fees
Oct 14 - Oct 15
Westchester House | Sleeps 10 | Near Chicago & Parks | Close to Restaurants & Easy Local Transport Access | Long private driveway
A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

4. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (64 reviews)
"We had a wonderful stay"
United States
Anonymous traveler
The price is ￥28,555
￥56,514 total
includes taxes & fees
Oct 14 - Oct 15
LUXE 3 BR, 2 BA + Hot Tub
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

5. Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood
7.8 out of 10, Good, (34 reviews)
"Very nice home with basement bar. Host was very accommodating."
United States
Carl T.
The price is ￥23,558
￥47,944 total
includes taxes & fees
Oct 14 - Oct 15
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Lake

6. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (66 reviews)
"First time staying there and we absolutely loved our stay. We will definitely be going back."
United States
Iliana
The price is ￥28,337
￥43,102 total
includes taxes & fees
Nov 10 - Nov 11
Kasa Lake Shore Chicago
Terrace/patio

7. 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 ￥30,407
￥52,428 total
includes taxes & fees
Oct 28 - Oct 29
At Home in Oak Park
A modern building with the name 'SENIORAL' prominently displayed on the facade.

8. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,370 reviews)
"Perfect location to stay at if attending the bears games !"
United States
Jacob
The price is ￥22,718
￥26,670 total
includes taxes & fees
Nov 9 - Nov 10
Sentral Michigan Avenue
A modern living room with teal sofas, a coffee table, and a TV.

9. Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
Northlake
10.0 out of 10, Exceptional, (25 reviews)
"The room was very clean, and the host was timely with communications. The couches and bed were so comfy!"
United States
Kaitlyn W.
The price is ￥20,580
￥25,404 total
includes taxes & fees
Nov 1 - Nov 2
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
A compact kitchen with dark wood cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

10. Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (82 reviews)
"Excellent place to stay!"
United States
Alicia K.
The price is ￥17,561
￥47,528 total
includes taxes & fees
Oct 26 - Oct 27
Cozy, Comfortable and Convenient apartment. Close to everything!
A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

11. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (286 reviews)
"Really helpful staff, really nice rooms."
United States
Archita
The price is ￥36,329
￥41,590 total
includes taxes & fees
Nov 12 - Nov 13
The Gem Museum Suites
A dining area with a table set for two, a black leather sofa, and a ceiling fan.

12. Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
Berwyn
9.8 out of 10, Exceptional, (35 reviews)
"Relaxing stay and safe location. Host JD provided great communication throughout the stay. Stores are nearby in case you need items for your trip. Food options are abundant in the area. 30 min drive to downtown Chicago."
United States
Cynthia M.
The price is ￥10,894
￥28,627 total
includes taxes & fees
Oct 14 - Oct 15
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
A living room with a gray sofa, a coffee table, a TV mounted on the wall, and a wooden door.

13. Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW

Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
Berwyn
9.8 out of 10, Exceptional, (23 reviews)
"Parking was free and right out front. Great apartment and the host was great with accommodations."
United States
Travis C.
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
A modern kitchen with a large island, bar stools, and a city view.

14. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (541 reviews)
"Great location, very clean, loved the gym and cafe!"
United States
Kerry
The price is ￥42,262
￥53,524 total
includes taxes & fees
Nov 1 - Nov 2
Level Chicago – Old Town
A modern living room with a grey sofa, white and patterned cushions, a round coffee table, and a ceiling fan.

15. Chic Suite/Mins to L Train /Laundry/Free Parking

Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9.4 out of 10, Exceptional, (73 reviews)
"Easy access to the Green Line."
United States
Michael
The price is ￥15,277
￥37,468 total
includes taxes & fees
Oct 26 - Oct 27
Chic Suite/Mins to L Train /Laundry/Free Parking
A glass elevator with a city view.

16. Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Oak Park
9.6 out of 10, Exceptional, (115 reviews)
"Excellent communication from the host, we also appreciated their modern, organized and clean home."
United States
Robin D.
The price is ￥21,416
￥46,311 total
includes taxes & fees
Oct 27 - Oct 28
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
A modern building with large glass windows, surrounded by a grassy area with trees and a pathway.

17. The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.4 out of 10, Exceptional, (8 reviews)
The price is ￥28,141
￥49,832 total
includes taxes & fees
Oct 27 - Oct 28
The Oak Park Loft
A living room with a brick fireplace, a flat-screen TV mounted above it, and a large potted plant.

18. Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP

Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Berwyn
9.2 out of 10, Wonderful, (41 reviews)
"Beautiful clean and comfy loved my stay"
United States
Tania W.
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
A hallway with a wooden floor, a bench, and two abstract paintings on the wall.

19. Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT

Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT
Berwyn
9.4 out of 10, Exceptional, (25 reviews)
"A very comfy older building that has been upgraded in several areas. Convenient to transportation, restaurants and local events. "
United States
Carrie
The price is ￥15,530
￥34,228 total
includes taxes & fees
Oct 14 - Oct 15
Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT
Private kitchen

20. 1BR Apartment - Walk to Shops - Downtown OAK PARK

1BR Apartment - Walk to Shops - Downtown OAK PARK
Oak Park
9.2 out of 10, Wonderful, (44 reviews)
"Great location! Enjoyed my stay!"
United States
Shannon H.
The price is ￥17,768
￥40,682 total
includes taxes & fees
Oct 27 - Oct 28
1BR Apartment - Walk to Shops - Downtown OAK PARK
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 Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

8/10 Good
"Friendly helpful staff. Nice clean room. Hot water was not working and of course it was late afternoon and I needed to shower before evening outing. Oh well, cold shower not the worst thing to endure."
Eric 2-night trip
Posted 1 hour ago
The Chicago Hotel Collection - Magnificent Mile

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.

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.