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.
The price is CA $281
CA $656 total
includes taxes & fees
May 26 - May 27
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 CA $447
CA $1,081 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 CA $264
CA $575 total
includes taxes & fees
May 25 - May 26
Modern Luxury 2BR Near Downtown Chicago - Sleeps 6 & Designer Stay

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 CA $138
CA $297 total
includes taxes & fees
May 26 - May 27
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, (760 reviews)
"Great place to stay."
United States
Benedictine
The price is CA $209
CA $327 total
includes taxes & fees
May 25 - May 26
Kasa Magnificent Mile Chicago

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, (6 reviews)
"This was a great stay! Great size and location. Would recommend it a lot."
United States
Dulce
The price is CA $138
CA $280 total
includes taxes & fees
May 26 - May 27
Chic Studio in the Heart of the Gold Coast

Modern 3BR Apartment Near North Ave Shops

Modern 3BR Apartment Near North Ave Shops
Near North Side
The price is CA $1,100
CA $1,863 total
includes taxes & fees
Jun 12 - Jun 13
Modern 3BR Apartment Near North Ave Shops

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,169 reviews)
"Spacious apartment with stunning view. A great stay!!"
United States
Tina
The price is CA $205
CA $282 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 CA $138
CA $297 total
includes taxes & fees
May 26 - May 27
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 CA $364
CA $828 total
includes taxes & fees
May 26 - May 27
River North Rooftop With In and Out Parking 3

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (480 reviews)
"Beautiful clean place. Great safe location within proximity to restaurants and transportation around the city with fantastic views. Would recommend and stay here again. "
Canada
Lissa
The price is CA $238
CA $313 total
includes taxes & fees
May 26 - May 27
Level Chicago – Old Town

Chicago-Themed 1BR in a Central Spot near Downtown

Chicago-Themed 1BR in a Central Spot near Downtown
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Clean spacious great location easy to get everywhere "
United States
Melissa M.
The price is CA $138
CA $297 total
includes taxes & fees
May 26 - May 27
Chicago-Themed 1BR in a Central Spot near Downtown

LIVN West Loop Chicago King Studio

LIVN West Loop Chicago King Studio
Downtown Chicago
10.0 out of 10, Exceptional, (4 reviews)
"Amazing studio apartment style room, super clean, very helpful staff, and great location."
United States
William
The price is CA $223
CA $299 total
includes taxes & fees
May 27 - May 28
LIVN West Loop Chicago King Studio

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 CA $188
CA $255 total
includes taxes & fees
May 25 - May 26
LIVN Millennium Park Downtown Chicago Studio

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
8.8 out of 10, Excellent, (3 reviews)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is CA $174
CA $344 total
includes taxes & fees
May 26 - May 27
1BR Modern Luxe Apt with In-Unit 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, (23 reviews)
"Everything was walking distance and had everything needed for a comfortable stay "
United States
Daniel
The price is CA $473
CA $1,152 total
includes taxes & fees
Jun 17 - Jun 18
Modern West Loop Gem-City Views & Prime Location 6

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 CA $515
CA $1,074 total
includes taxes & fees
May 24 - May 25
Spacious 4BR Central Apartment w/ Skyline Views

Downtown Chicago Stay with Free In & Out Parking 3

Downtown Chicago Stay with Free In & Out Parking 3
Downtown Chicago
10.0 out of 10, Exceptional, (4 reviews)
"Perfect Stay!"
United States
Miyauna G.
The price is CA $587
CA $1,132 total
includes taxes & fees
Jun 21 - Jun 22
Downtown Chicago Stay with Free In & Out Parking 3

Cozy Boho Chicago - 10 Minutes to Downtown Chicago

Cozy Boho Chicago - 10 Minutes to Downtown Chicago
Lawndale
9.8 out of 10, Exceptional, (10 reviews)
"Wonderful space and convenient location. Really responsive host and super quiet neighborhood! "
United States
Jess S.
The price is CA $126
CA $310 total
includes taxes & fees
Jun 16 - Jun 17
Cozy Boho Chicago - 10 Minutes to Downtown Chicago

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
North Center
9.6 out of 10, Exceptional, (74 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is CA $197
CA $472 total
includes taxes & fees
May 25 - May 26
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Westchester. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.