Westchester Vacation Rentals from ￥9,866: Search Short-Term Rentals

Q: 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.

Q: 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.

Q: How many vacation rentals are there in Westchester?

Expedia has 5 vacation rentals for your stay in Westchester.

Q: 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 Soldier Field in the larger area.

Q: 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.

A calm lake with ducks, autumn trees, and a grassy park area.

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Our top choices for Westchester vacation rentals

A hotel lobby with sofas, a reception desk, a staircase, and a view of the outside.

1. Kasa Lake Shore Chicago

Downtown Chicago

Jair

￥35,419 total

includes taxes & fees

Nov 22 - Nov 23

A high-rise building with a glass facade, surrounded by other buildings.

2. Sentral Michigan Avenue

Downtown Chicago

Jeff

￥35,859 total

includes taxes & fees

Dec 6 - Dec 7

A two-story house with a brick exterior, a sloped roof, and a front porch.

3. At Home in Oak Park

Oak Park

Melissa

A spacious lobby with a high ceiling, a reception desk, comfortable seating, and a large stained glass window.

4. The Gem Museum Suites

Downtown Evanston

Ernest

￥36,581 total

includes taxes & fees

Nov 15 - Nov 16

A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

5. Wrigleyville Suites

Lakeview

Francisco

￥22,058 total

includes taxes & fees

Dec 7 - Dec 8

A two-story house with a front porch, a staircase leading to the second floor, and a well-maintained garden.

6. Classic Forest Park Foursquare < 1 Mi to Blue Line

Forest Park

￥75,863 total

includes taxes & fees

Nov 18 - Nov 19

A high-rise building with multiple floors, large windows, and a modern architectural design.

7. Level Chicago – Old Town

Downtown Chicago

Robert Edward

￥36,183 total

includes taxes & fees

Nov 22 - Nov 23

A two-story house with a prominent evergreen tree in front, surrounded by various shrubs and a driveway.

8. Historic Oak Park Home

Oak Park

Janette

￥56,962 total

includes taxes & fees

Nov 16 - Nov 17

A residential street with a well-maintained garden, a large coniferous tree, and a house in the background.

9. Historic Oak Park Residence

Oak Park

Ann-Marie

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Find vacation rentals that suit your style

Top Westchester Hotel Reviews

Four Points by Sheraton Chicago Westchester/Oak Brook

Westchester

10/10 Excellent

Gary

A hotel entrance with a prominent 'MORTON' sign, a 'HOTEL BLAKE CHICAGO' sign, and a '542' address number.

Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

10/10 Excellent

Jennifer

A hotel room with two beds, a desk, a chair, and a large window.

SureStay Plus Hotel by Best Western Chicago Lombard

Highland Hills

10/10 Excellent

Margaret

A modern living room with a large window overlooking a body of water, a tripod, and a sofa.

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

10/10 Excellent

Griffin

A bar area with a long counter, multiple stools, and shelves stocked with bottles.

L7 CHICAGO by LOTTE HOTELS

Downtown Chicago

10/10 Excellent

Erin

A cityscape at dusk with high-rise buildings, including a Hilton hotel.

Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

10/10 Excellent

I was traveling with two 14 year olds on a business/vacation trip and we stayed here for five days. The location is great. I wanted a hotel that was convenient to the major attractions and downtown, and safe for the boys to walk around on their own. We were able to walk to Navy Pier, Millennium Park, the Loop, and the Hancock Building. It's a good 20-25 minute walk to Navy Pier, but you walk along Lakeshore Drive and it's very enjoyable. The property is very nice, although we didn't get the two...

Joanna

A bar area with a checkered floor, bar stools, and a well-lit sign above the bar.

ACME Hotel Chicago, Outset Collection by Hilton

Downtown Chicago

10/10 Excellent

Three day trip to Chicago. The hotel was a great central location in downtown and a 10 to 15 minute walk to most sites, Navy Pier, River walk, Michigan Avenue, all the great pizza places. The hotel was smaller compared to most which we loved. Room was updated, bathroom very nice and king sized bed very comfortable. We used the blue line to get to and from O’Hare via Clark station (a 12 minute walk from hotel.). We used the red line via Chicago station (10 min walk from hotel) to go see a Cubs...

Claudia

A modern lounge area with seating, a bar, and large windows offering views.

Hyatt House Chicago/West Loop-Fulton Market

Downtown Chicago

10/10 Excellent

The staff was amazing and the room was super spacious and clean!! The best layout of a room for a family of 3 who enjoy separate beds and a little privacy. We had the room with two queen beds and a sofa. Amazing view of chicago from the sky deck and the pool was a nice temp! Breakfast had great options and was delicious! Rosemary seasoned potatoes and captain crunch caught my eye! The elevator was a bit hard to navigate at times as you need a key. But great safety feature so no complaints!...

Valia

A modern interior with a geometric light wall, a staircase, and hanging crystal chandeliers.

Hampton Inn & Suites Chicago Downtown

Downtown Chicago

10/10 Excellent

Shatani

An outdoor rooftop lounge with seating, planters, and a view of surrounding high-rise buildings.

Hampton Inn Chicago West Loop Fulton Market Area

Downtown Chicago

10/10 Excellent

We will definitely be staying here again! Great location, clean room, and great service. They even have a great complimentary breakfast which is a must have in a city like Chicago. The staff was great also. We had to switch trains for an earlier one due to weather and got into Chicago in the AM. Check in is 4pm and with two small children we were worried about what to do for hours but the staff helped us out and luckily had a room available.

Alexander

A hotel entrance with a sign for Fairfield Inn & Suites by Marriott.

Fairfield Inn & Suites Chicago Downtown/River North

Downtown Chicago

10/10 Excellent

Claribeth

The exterior of the Majestic Building with a prominent entrance, a neon sign, and decorative elements.

Hampton Inn Majestic Chicago Theatre District

Downtown Chicago

10/10 Excellent

Anne

A high-rise building with multiple balconies and a view of a marina below.

Hotel Chicago Downtown, Autograph Collection by Marriott

Downtown Chicago

10/10 Excellent

Abdullah

A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.

DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

10/10 Excellent

Rudy

A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

10/10 Excellent

blerina

Arlo Chicago

Downtown Chicago

10/10 Excellent

Arlo Chicago is in the perfect location for walkable access to so many Chicago sights, excellent food (please try the Broken English Taco Pub around the corner!), bars, shopping, etc. It was also very conveniently located to access the L when we needed to get to other parts of the city! The staff was BEYOND accommodating, friendly, and helpful. The room was clean and exceeded all comfort expectations! I also highly recommend the lobby bar for a great happy hour spot!!! Everyone at this hotel...

Lina

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?

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 5 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 Soldier Field 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.

Westchester Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Westchester vacation rentals

1. Kasa Lake Shore Chicago

2. Sentral Michigan Avenue

3. At Home in Oak Park

4. The Gem Museum Suites

5. Wrigleyville Suites

6. Classic Forest Park Foursquare < 1 Mi to Blue Line

7. Level Chicago – Old Town

8. Historic Oak Park Home

9. Historic Oak Park Residence

Find vacation rentals that suit your style

Top Westchester Hotel Reviews

Four Points by Sheraton Chicago Westchester/Oak Brook

10/10 Excellent

Find out more about Westchester

Frequently Asked Questions

Can I find vacation rentals in Westchester?

What are some of the best vacation rentals that Westchester has to offer?

How many vacation rentals are there in Westchester?

What can I see and do in Westchester?

What are vacation rentals like in Westchester?