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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 ¥30,703
¥65,687 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 ¥52,052
¥128,027 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

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,184 reviews)
"Great location"
United States
JAVIER
The price is ¥28,497
¥38,162 total
includes taxes & fees
Jul 1 - Jul 2
Sentral Michigan Avenue

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (788 reviews)
"Great place to stay."
United States
Benedictine
The price is ¥42,618
¥59,446 total
includes taxes & fees
Jun 11 - Jun 12
Kasa Magnificent Mile Chicago

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 ¥84,215
¥157,168 total
includes taxes & fees
Jun 25 - Jun 26
ENVITAE Hotel, 4BR Luxury Modern Apartments

3BR Luxury Suite w/Gym and Balcony

3BR Luxury Suite w/Gym and Balcony
Downtown Chicago
9.4 out of 10, Exceptional, (30 reviews)
"The apartment is in a good location, close to restaurants and bars. There is a nice park not far away and we had a lovely stay. "
United States
shayna j.
The price is ¥61,277
¥125,897 total
includes taxes & fees
Jul 8 - Jul 9
3BR Luxury Suite w/Gym and Balcony

River North Rooftop With In and Out Parking 1

River North Rooftop With In and Out Parking 1
Downtown Chicago
9.8 out of 10, Exceptional, (6 reviews)
"Awesome location, great place would definitely recommend will hopefully return"
United States
lucas c.
The price is ¥46,679
¥93,143 total
includes taxes & fees
Jun 21 - Jun 22
River North Rooftop With In and Out Parking 1

LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
9.6 out of 10, Exceptional, (5 reviews)
The price is ¥54,615
¥73,014 total
includes taxes & fees
Jun 16 - Jun 17
LIVN West Loop Chicago 2 BR City View

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (18 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 ¥52,935
¥113,028 total
includes taxes & fees
Jul 5 - Jul 6
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, (490 reviews)
"Very clean and loved the location and amenities with the store on the first floor was fantastic"
United States
Kimberly
The price is ¥40,279
¥51,241 total
includes taxes & fees
Jun 30 - Jul 1
Level Chicago – Old Town

River North Rooftop With In and Out Parking 6

River North Rooftop With In and Out Parking 6
Downtown Chicago
9.0 out of 10, Wonderful, (2 reviews)
"Host was amazing, very responsive. VRBO was spotless! Great location! Would definitely stay here again."
United States
Amy L.
The price is ¥51,331
¥108,885 total
includes taxes & fees
Jun 28 - Jun 29
River North Rooftop With In and Out Parking 6

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 ¥28,874
¥95,829 total
includes taxes & fees
Jun 28 - Jun 29
Modern West Loop Gem-City Views & Prime Location 6

LIVN Millennium Park Downtown Chicago Superior 1BR

LIVN Millennium Park Downtown Chicago Superior 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Excelente, well located. Recommended."
United States
Sandra S.
The price is ¥42,669
¥51,856 total
includes taxes & fees
Jun 15 - Jun 16
LIVN Millennium Park Downtown Chicago Superior 1BR

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood
8.0 out of 10, Very Good, (28 reviews)
"Was a very nice stay and the host was very helpful and got very quick responses "
United States
Eduardo
The price is ¥23,784
¥48,061 total
includes taxes & fees
Jun 16 - Jun 17
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (6 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is ¥19,360
¥39,976 total
includes taxes & fees
Jun 14 - Jun 15
The Oak Park Loft

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 ¥32,242
¥56,122 total
includes taxes & fees
Jun 21 - Jun 22
Sunlit 1BR Apartment | Warm & Welcoming Space

Your Next Vacation Home

Your Next Vacation Home
Oakton
9.4 out of 10, Exceptional, (77 reviews)
"Well welcoming and kind. I’m glad we stayed here. "
United States
Justi N.
The price is ¥40,423
¥68,127 total
includes taxes & fees
Jun 11 - Jun 12
Your Next Vacation Home

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, (77 reviews)
"Great location for a short trip "
United States
Eric W.
The price is ¥25,537
¥58,626 total
includes taxes & fees
Jun 21 - Jun 22
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (132 reviews)
"Perfect place to stay!"
United States
Anton
The price is ¥24,398
¥27,932 total
includes taxes & fees
Jun 17 - Jun 18
The Gem Museum Suites

Spacious and family friendly getaway. 8 mins from Chicago Premium Outlet Mall.

Spacious and family friendly getaway. 8 mins from Chicago Premium Outlet Mall.
Aurora
10.0 out of 10, Exceptional, (32 reviews)
"Great place to stay! Easy to check-in and check-out. We didn't have any issues with the house or host. Would stay again."
United States
Ava B.
The price is ¥72,040
¥174,609 total
includes taxes & fees
Jun 11 - Jun 12
Spacious and family friendly getaway. 8 mins from Chicago Premium Outlet Mall.
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 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.