Westchester Vacation Rentals

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Our top choices for Westchester vacation rentals

King Bed, Game Room & Fire Pit | LCP Collection

King Bed, Game Room & Fire Pit | LCP Collection
Westchester
8.0 out of 10, Very Good, (3 reviews)
"Great location, price and the place was well kept and accommodating."
United States
Carl M.
The price is ¥35,388
¥80,143 total
includes taxes & fees
Mar 26 - Mar 27
King Bed, Game Room & Fire Pit | LCP Collection

Cozy Westchester Retreat Near Chicago & Parks

Cozy Westchester Retreat Near Chicago & Parks
Westchester
The price is ¥47,607
¥104,718 total
includes taxes & fees
Mar 26 - Mar 27
Cozy Westchester Retreat Near Chicago & Parks

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 ¥23,010
¥43,741 total
includes taxes & fees
Mar 29 - Mar 30
Sun-Drenched 1BR Apartment

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
9.4 out of 10, Exceptional, (16 reviews)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is ¥16,980
¥35,697 total
includes taxes & fees
Mar 29 - Mar 30
Modern Comfort: 1BR Unit w/ Laundry

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (8 reviews)
"Great communication and hosts. Location and unit was perfect."
United States
Greg C.
The price is ¥21,264
¥41,307 total
includes taxes & fees
Mar 29 - Mar 30
West Loop Living – Bright 1BR

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 ¥17,932
¥34,836 total
includes taxes & fees
Mar 29 - Mar 30
Chic Studio in the Heart of the Gold Coast

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (719 reviews)
"Great place "
United States
Lamees
Kasa Magnificent Mile Chicago

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,114 reviews)
"Clean spacious my go to vacation spot all year around "
United States
xavier
The price is ¥17,402
¥25,086 total
includes taxes & fees
Apr 1 - Apr 2
Sentral Michigan Avenue

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 ¥25,390
¥72,469 total
includes taxes & fees
Apr 14 - Apr 15
River North Rooftop With In and Out Parking 3

Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 6
Downtown Chicago
10.0 out of 10, Exceptional, (17 reviews)
"Great place"
United States
Daniel L.
The price is ¥33,166
¥100,873 total
includes taxes & fees
Mar 29 - Mar 30
Modern West Loop Gem-City Views & Prime Location 6

Nice 1BR Spot, Unwind & Relax

Nice 1BR Spot, Unwind & Relax
Lincoln Square
9.8 out of 10, Exceptional, (28 reviews)
"Very clean & cozy! Conveniently located by great shopping & restaurants!"
United States
SHERI C.
The price is ¥13,013
¥30,267 total
includes taxes & fees
Mar 26 - Mar 27
Nice 1BR Spot, Unwind & Relax

Homey 1BR Space Apartment

Homey 1BR Space Apartment
Lincoln Square
9.6 out of 10, Exceptional, (16 reviews)
"Love the location right in Lincoln Square. "
United States
Ticia B.
The price is ¥13,965
¥31,581 total
includes taxes & fees
Mar 30 - Mar 31
Homey 1BR Space Apartment

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (451 reviews)
"Great value, friendly staff"
United States
Marcus
The price is ¥26,050
¥34,493 total
includes taxes & fees
Mar 29 - Mar 30
Level Chicago – Old Town

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

Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9.6 out of 10, Exceptional, (60 reviews)
"Comfortable bed, spacious rooms and clean."
United States
Michael W.
The price is ¥10,197
¥30,749 total
includes taxes & fees
Mar 30 - Mar 31
Chic Suite/Mins to L Train /Laundry/Free Parking

Your Perfect 2BR Home

Your Perfect 2BR Home
Near West Side
8.4 out of 10, Very Good, (15 reviews)
"Great location! "
United States
Kourtney K.
The price is ¥13,965
¥35,145 total
includes taxes & fees
Mar 26 - Mar 27
Your Perfect 2BR Home

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, (7 reviews)
"Had a great experience here, and also close to the airport!"
United States
Yafeat D.
The price is ¥15,076
¥19,524 total
includes taxes & fees
Mar 26 - Mar 27
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is ¥19,152
¥39,547 total
includes taxes & fees
Mar 30 - Mar 31
The Oak Park Loft

Uptown Studio Gem Sum

Uptown Studio Gem Sum
Uptown
7.4 out of 10, Good, (6 reviews)
"The neighborhood was perfect for me. I’d like to book the same property again because of the location.The only problem was checking in. The address was wrong and if I wasn’t raised in that part of Chicago I would have been very confused.Plus I checked in late at night. It wasn’t an easy process. Next time it will be diffeeent."
United States
Darryl C.
The price is ¥14,917
¥30,911 total
includes taxes & fees
Mar 29 - Mar 30
Uptown Studio Gem Sum

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, (65 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is ¥21,280
¥52,496 total
includes taxes & fees
Mar 29 - Mar 30
2-bedroom apartment just 2 minutes drive to Wrigley Field

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (187 reviews)
"Nice area if you are renting a car, be aware that you would have to pay for street parking or go over a few blocks and park in a parking lot."
United States
Daysha
The price is ¥20,137
¥36,679 total
includes taxes & fees
Apr 5 - Apr 6
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

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:

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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?

A Home Away From Home!: This vacation home rental outside of Westchester offers a fireplace, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

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.