Westchester Vacation Rentals

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Our top choices for Westchester vacation rentals

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 location and the place was immaculate. Host was very nice."
United States
Carl M.
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

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
The price is ¥50,921
¥122,182 total
includes taxes & fees
May 25 - May 26
Westchester House | Sleeps 10 | Near Chicago & Parks | Close to Restaurants & Easy Local Transport Access | Long private driveway

Modern Luxury 2BR Near Downtown Chicago - Sleeps 6 & Designer Stay

Modern Luxury 2BR Near Downtown Chicago - Sleeps 6 & Designer Stay
Westchester
The price is ¥30,036
¥65,488 total
includes taxes & fees
May 11 - May 12
Modern Luxury 2BR Near Downtown Chicago - Sleeps 6 & Designer Stay

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)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is ¥18,175
¥35,139 total
includes taxes & fees
May 13 - May 14
Chic Studio in the Heart of the Gold Coast

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
8.8 out of 10, Excellent, (18 reviews)
"Great location, apt well equipped and host very responsive. Wonderful stay. "
United States
Gina G.
The price is ¥23,032
¥43,941 total
includes taxes & fees
May 26 - May 27
Modern Comfort: 1BR Unit w/ Laundry

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, (22 reviews)
"Everything was walking distance and had everything needed for a comfortable stay "
United States
Daniel
The price is ¥25,696
¥90,121 total
includes taxes & fees
May 13 - May 14
Modern West Loop Gem-City Views & Prime Location 6

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
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 ¥35,410
¥60,567 total
includes taxes & fees
May 21 - May 22
Sunlit 1BR Apartment | Warm & Welcoming Space

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (751 reviews)
"Great location"
United States
Alex
The price is ¥25,151
¥38,722 total
includes taxes & fees
May 11 - May 12
Kasa Magnificent Mile Chicago

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,156 reviews)
"Spacious apartment with stunning view. A great stay!!"
United States
Tina
The price is ¥23,839
¥32,582 total
includes taxes & fees
May 25 - May 26
Sentral Michigan Avenue

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
9.8 out of 10, Exceptional, (10 reviews)
"Great spot next to the green line train a few restaurants and a Starbucks right up the street I will book again for sure "
United States
2k G.
The price is ¥27,889
¥49,823 total
includes taxes & fees
May 13 - May 14
West Loop Living – Bright 1BR

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, (5 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 ¥41,520
¥95,524 total
includes taxes & fees
May 26 - May 27
River North Rooftop With In and Out Parking 3

LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
The price is ¥146,496
¥194,996 total
includes taxes & fees
May 15 - May 16
LIVN Millennium Park Downtown Chicago 2BR

LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
The price is ¥29,299
¥39,424 total
includes taxes & fees
May 14 - May 15
LIVN West Loop Chicago Queen Superior Studio

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (17 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
The price is ¥60,949
¥123,355 total
includes taxes & fees
Jun 1 - Jun 2
Spacious 4BR Central Apartment w/ Skyline Views

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (474 reviews)
"Love the amenities. Great location too"
United States
Paul
The price is ¥34,139
¥43,940 total
includes taxes & fees
May 26 - May 27
Level Chicago – Old Town

River North Private Deck With In and Out Parking

River North Private Deck With In and Out Parking
Downtown Chicago
9.6 out of 10, Exceptional, (9 reviews)
"Excellent location, very clean, spacious."
United States
John David K.
The price is ¥144,929
¥245,801 total
includes taxes & fees
May 15 - May 16
River North Private Deck With In and Out Parking

Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 3
Downtown Chicago
10.0 out of 10, Exceptional, (7 reviews)
"Loved the place 4 bedroom & 4 bathrooms was ideal for our stayGreat locationLoved the well stocked convenience store a block away "
United States
Tina Y.
The price is ¥24,599
¥89,927 total
includes taxes & fees
May 20 - May 21
Modern West Loop Gem-City Views & Prime Location 3

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (192 reviews)
"Great property - would come back. Decent size rooms and generally good all around"
United States
Suyash
The price is ¥28,743
¥46,618 total
includes taxes & fees
May 11 - May 12
Kasa River North Chicago

LIVN Millennium Park Downtown Chicago Superior 2 BR

LIVN Millennium Park Downtown Chicago Superior 2 BR
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Very nice place and reasonable price."
United States
Maya K.
The price is ¥96,358
¥128,399 total
includes taxes & fees
May 15 - May 16
LIVN Millennium Park Downtown Chicago Superior 2 BR

LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Great location, lovely furnishings and amenities."
United States
Georgina E.
The price is ¥21,465
¥29,067 total
includes taxes & fees
May 12 - May 13
LIVN Millennium Park Downtown Chicago Studio
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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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?

ENVITAE Hotel, 4BR Luxury Modern Apartments: This vacation home rental outside of Westchester is located in the city center and offers a barbecue grill, air-conditioning, and laundry facilities to help you feel perfectly comfortable 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 10 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 Navy Pier 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.