Westchester Vacation Rentals

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Check prices for these dates

In two weeks
Mar 20 - Mar 22
In two months
May 1 - May 3
In three months
May 29 - May 31
In four months
Jun 26 - Jun 28

Our top choices for Westchester vacation rentals

Fridge, microwave, oven, stovetop

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
9.8 out of 10, Exceptional, (20 reviews)
"Great place Great location "
United States
Josh W.
The price is ￥28,495
￥69,644 total
includes taxes & fees
Mar 8 - Mar 9
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
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 ￥35,002
￥79,269 total
includes taxes & fees
Mar 18 - Mar 19
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 ￥43,390
￥99,391 total
includes taxes & fees
Mar 8 - Mar 9
Cozy Westchester Retreat Near Chicago & Parks
Fridge, microwave, oven, stovetop

Modern 3BR Home w/ Huge Backyard | LCP Collection

Modern 3BR Home w/ Huge Backyard | LCP Collection
Westchester
10.0 out of 10, Exceptional, (1 review)
"Everything was exactly like we hoped and ghen sum. Great single level floor plan with garage access."
United States
Alva E.
The price is ￥30,767
￥74,281 total
includes taxes & fees
Mar 31 - Apr 1
Modern 3BR Home w/ Huge Backyard | LCP Collection
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 ￥17,736
￥36,220 total
includes taxes & fees
Mar 11 - Mar 12
Sun-Drenched 1BR Apartment
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 ￥23,544
￥60,152 total
includes taxes & fees
Mar 8 - Mar 9
River North Rooftop With In and Out Parking 3
Fridge, microwave, oven, stovetop

Sleek 1BR Apartment w/ In-unit Laundry

Sleek 1BR Apartment w/ In-unit 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 traveler
The price is ￥17,736
￥35,637 total
includes taxes & fees
Mar 18 - Mar 19
Sleek 1BR Apartment w/ In-unit Laundry
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 ￥17,736
￥36,607 total
includes taxes & fees
Mar 12 - Mar 13
Modern Comfort: 1BR Unit w/ Laundry
1 bedroom, iron/ironing board, travel crib, 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 ￥17,736
￥36,411 total
includes taxes & fees
Mar 8 - Mar 9
West Loop Living – Bright 1BR
Dining room

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (705 reviews)
"Perfect location and very clean! "
United States
Latoya
Kasa Magnificent Mile Chicago
Desk, iron/ironing board, travel crib, 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)
"We had a wonderful stay at this Vrbo! The home was spotless, cozy, and exactly as described. The host was friendly, responsive, and made everything easy from check-in to check-out. We would absolutely stay here again. Highly recommend!"
United States
Brianna K.
The price is ￥17,736
￥34,455 total
includes taxes & fees
Mar 8 - Mar 9
Chic Studio in the Heart of the Gold Coast
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,098 reviews)
"Best full kitchen multi-room family lodging"
United States
Lee
The price is ￥19,881
￥27,946 total
includes taxes & fees
Apr 5 - Apr 6
Sentral Michigan Avenue
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 ￥17,736
￥36,411 total
includes taxes & fees
Mar 8 - Mar 9
1BR Modern Luxe Apt with In-Unit Laundry
Full-size fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (436 reviews)
"Clean, nice amenities and great staff."
United States
Sydnee
Level Chicago – Old Town
Exterior

A quiet stay while you are away

A quiet stay while you are away
Oak Park
9.8 out of 10, Exceptional, (34 reviews)
"Everything was very comfortable and Jay did a great job of showing the house. I would definitely come back again"
United States
Fred D.
The price is ￥14,902
￥37,834 total
includes taxes & fees
Mar 10 - Mar 11
A quiet stay while you are away
TV, offices

Ideal 2BR Getaway Close to Attractions

Ideal 2BR Getaway Close to Attractions
Rogers Park
8.4 out of 10, Very Good, (7 reviews)
"Loved this sweet space tucked into a special neighborhood in the city. Space was clean & comfortable, wonderful shower & a nice respite from city life. "
United States
Ever
The price is ￥13,656
￥33,212 total
includes taxes & fees
Mar 17 - Mar 18
Ideal 2BR Getaway Close to Attractions
Exterior

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (9 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
The price is ￥110,288
￥192,753 total
includes taxes & fees
Mar 11 - Mar 12
Spacious 4BR Central Apartment w/ Skyline Views
Property grounds

2-bedroom apartment just 2 minutes drive to Wrigley Field

2-bedroom apartment just 2 minutes drive to Wrigley Field
North Center
9.6 out of 10, Exceptional, (59 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is ￥18,223
￥47,273 total
includes taxes & fees
Mar 8 - Mar 9
2-bedroom apartment just 2 minutes drive to Wrigley Field
Interior

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, (4 reviews)
"Had a great experience here, and also close to the airport!"
United States
Yafeat D.
The price is ￥14,911
￥19,311 total
includes taxes & fees
Mar 17 - Mar 18
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (185 reviews)
"Awesome stay "
United States
Sally
Kasa River North Chicago
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/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"Clean room spacious friendly staff"
Theresa 4-night trip
Posted 2 hours ago
Hilton Chicago/Magnificent Mile Suites

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?

Wrigley Field/Lakeview -Entire Home- Large Groups!: This vacation home rental outside of Westchester is located on a lake and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Westchester?

Expedia has 9 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 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.