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Westchester Vacation Rentals

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Our top choices for Westchester vacation rentals

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 $268
CA $585 total
includes taxes & fees
Jun 16 - Jun 17
Modern Luxury 2BR Near Downtown Chicago - Sleeps 6 & Designer Stay

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 $455
CA $1,100 total
includes taxes & fees
Jun 16 - Jun 17
Westchester House | Sleeps 10 | Near Chicago & Parks | Close to Restaurants & Easy Local Transport Access | Long private driveway

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
Chic Studio in the Heart of the Gold Coast

River North Rooftop With In and Out Parking 5

River North Rooftop With In and Out Parking 5
Downtown Chicago
9.6 out of 10, Exceptional, (5 reviews)
"Everything was amazing, property was even better than expected"
United States
Jacob
The price is CA $390
CA $788 total
includes taxes & fees
Jul 9 - Jul 10
River North Rooftop With In and Out Parking 5

River North Private Balcony With In and Out Parking

River North Private Balcony With In and Out Parking
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"Place was easily accessible- very clean and an amazing alternative to hotel living for 2 colleagues. Coffee was available and all the basics of a hotel. "
United States
Rae M.
The price is CA $407
CA $817 total
includes taxes & fees
Jul 12 - Jul 13
River North Private Balcony With In and Out Parking

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,190 reviews)
"Great location"
United States
JAVIER
The price is CA $249
CA $333 total
includes taxes & fees
Jul 1 - Jul 2
Sentral Michigan Avenue

LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
10.0 out of 10, Exceptional, (7 reviews)
"The service was top notch at this property. The hosts were super responsive and professional. The location was incredible. Loved being able to cook in the apartment. The apartment was newly renovated and very urban chic. "
United States
Michelle R.
The price is CA $318
CA $425 total
includes taxes & fees
Jun 21 - Jun 22
LIVN West Loop Chicago Queen Superior Studio

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
Downtown Chicago
8.0 out of 10, Very good, (3 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 $206
CA $392 total
includes taxes & fees
Jun 21 - Jun 22
Sunlit 1BR Apartment | Warm & Welcoming Space

ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.6 out of 10, Exceptional, (13 reviews)
"Un superbe building avec des prestations sympas, un chouette appartement avec tout ce qu’il faut pour être confortable et les petits détails qui font la différence, notamment pour un court séjour car cela évite de voyager avec ou de courir en acheter: savon pour les mains, shampooing, gel douche, lessive, café etc il est très proche de la ligne rouge du métro et d’un arrêt de bus. "
United States
Emeline B.
The price is CA $477
CA $1,025 total
includes taxes & fees
Jul 8 - Jul 9
ENVITAE Hotel, 4BR Luxury Modern Apartments

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
9.2 out of 10, Wonderful, (12 reviews)
"The host was great at communicating and the apartment was very clean! "
United States
Hannah C.
The price is CA $242
CA $442 total
includes taxes & fees
Jun 22 - Jun 23
West Loop Living – Bright 1BR

3BR Luxury Suite w/Gym and Balcony

3BR Luxury Suite w/Gym and Balcony
Downtown Chicago
9.4 out of 10, Exceptional, (30 reviews)
"A wonderful place to stay and everything was so perfect! Could not recommend staying here enough! "
United States
Cassidy L.
The price is CA $550
CA $1,129 total
includes taxes & fees
Jul 8 - Jul 9
3BR Luxury Suite w/Gym and Balcony

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (20 reviews)
"Great place! The location is perfect. The apartment was comfortable for 5 people. Love the king beds in each room.It was clean and the staff was very helpful.Would definitely stay here again!"
United States
valerie h.
The price is CA $446
CA $982 total
includes taxes & fees
Jul 5 - Jul 6
Spacious 4BR Central Apartment w/ Skyline Views

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 $270
CA $480 total
includes taxes & fees
Jun 30 - Jul 1
Chicago-Themed 1BR in a Central Spot near Downtown

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (493 reviews)
"Very clean and loved the location and amenities with the store on the first floor was fantastic"
United States
Kimberly
The price is CA $353
CA $448 total
includes taxes & fees
Jun 29 - Jun 30
Level Chicago – Old Town

LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"Great location, lovely furnishings and amenities."
United States
Georgina E.
The price is CA $271
CA $367 total
includes taxes & fees
Jun 21 - Jun 22
LIVN Millennium Park Downtown Chicago Studio

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 $375
CA $1,022 total
includes taxes & fees
Jun 28 - Jun 29
Modern West Loop Gem-City Views & Prime Location 6

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, (80 reviews)
"Great location for a short trip "
United States
Eric W.
The price is CA $223
CA $511 total
includes taxes & fees
Jun 21 - Jun 22
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (82 reviews)
"Great stay i loved it"
United States
Cedes W.
The price is CA $151
CA $273 total
includes taxes & fees
Jun 21 - Jun 22
Cozy studio in Andersonville Chicago

Premium Urban 4BR - Perfect Mix of Comfort & Location

Premium Urban 4BR - Perfect Mix of Comfort & Location
Near North Side
10.0 out of 10, Exceptional, (1 review)
"Nice place, clean property, great views "
United States
Zach L.
The price is CA $758
CA $1,400 total
includes taxes & fees
Jul 9 - Jul 10
Premium Urban 4BR - Perfect Mix of Comfort & Location

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Worth
9.6 out of 10, Exceptional, (62 reviews)
"Home was exactly what we were needing fir our stay. Host was responsive and timely. "
United States
Stephanie H.
The price is CA $267
CA $561 total
includes taxes & fees
Jul 9 - Jul 10
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
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.

Explore a world of travel with Expedia

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 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 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.