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

Westchester Vacation 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: 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.

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Dates

November 2026

December 2026

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Our top choices for Westchester vacation rentals

A modern living room with a sofa, a round coffee table, and a dining area with a table and chairs.

1. Kasa Lake Shore Chicago

Downtown Chicago

Jair

NT$7,883 total

includes taxes & fees

Nov 22 - Nov 23

A modern building with the name 'SENIORAL' prominently displayed on the facade.

2. Sentral Michigan Avenue

Downtown Chicago

Jeff

NT$7,173 total

includes taxes & fees

Nov 12 - Nov 13

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

3. At Home in Oak Park

Oak Park

Melissa

NT$11,298 total

includes taxes & fees

Nov 12 - Nov 13

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

NT$7,515 total

includes taxes & fees

Nov 12 - Nov 13

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

NT$4,577 total

includes taxes & fees

Dec 7 - Dec 8

A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

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

Forest Park

NT$15,585 total

includes taxes & fees

Nov 16 - Nov 17

A modern kitchen with a large island, bar stools, and a city view.

7. Level Chicago – Old Town

Downtown Chicago

Robert Edward

NT$7,884 total

includes taxes & fees

Nov 23 - Nov 24

A spacious living room with a grand piano, a comfortable sofa, and a dining area with a chandelier.

8. Historic Oak Park Home

Oak Park

Janette

NT$11,694 total

includes taxes & fees

Nov 16 - Nov 17

A building with a white exterior and a tree with white blossoms in front.

9. Historic Oak Park Residence

Oak Park

Ann-Marie

View all properties

Find vacation rentals that suit your style

Top Westchester Hotel Reviews

A modern hotel lobby with a bar area, seating arrangements, and a television screen.

Four Points by Sheraton Chicago Westchester/Oak Brook

Westchester

10/10 Excellent

Gary

A spacious dining area with multiple tables and chairs, large windows with a view of the city, and a modern ceiling design.

SureStay Plus Hotel by Best Western Chicago Lombard

Highland Hills

10/10 Excellent

Margaret

A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

10/10 Excellent

Jennifer

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 hotel with a glass facade, a waterfront location, and a large Ferris wheel in the background.

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

10/10 Excellent

Griffin

A modern hotel lobby with a glass ceiling, white seating areas, and a view of the city.

The Godfrey Hotel Chicago

Downtown Chicago

10/10 Excellent

Julie

A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.

L7 CHICAGO by LOTTE HOTELS

Downtown Chicago

10/10 Excellent

Erin

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

A rooftop lounge with a city view, featuring a sofa, tables, and a fire feature.

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 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

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 cityscape at dusk with illuminated skyscrapers, a river, and a bridge.

Swissotel - Chicago

Downtown Chicago

10/10 Excellent

Brian

The Claridge House building with a sign, American and another flag, and outdoor seating with umbrellas.

Claridge House Chicago, Tapestry Collection by Hilton

Downtown Chicago

10/10 Excellent

This lovely hotel is nestled in a neighborhood that is quiet and very upscale. There are several restaurants in the area as well as a bar and restaurant (serving limited light fare) in the hotel lobby. For our purposes, it was located and very walkable. Our room was spacious and very well appointed. We stayed in a deluxe king room that offered a sitting area as well as a sleeping area. The decor was understated but elegant and comfortable. the bathroom featured a walk in shower which we prefer...

jolynn

A hotel room with a view of a cityscape through a large window, a floor lamp, a sofa with cushions, and a small table with a plant.

Sports Illustrated Resorts Chicago

Downtown Chicago

10/10 Excellent

William

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 modern interior with a geometric bookshelf filled with books, a bench, and a lamp.

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

A hotel with a classic facade, large windows, and flags.

Residence Inn Chicago Downtown/Loop

Downtown Chicago

10/10 Excellent

Sergio

A hotel room with a sofa, a small table, and a view of the cityscape through large windows.

Fairfield Inn & Suites Chicago Downtown/River North

Downtown Chicago

10/10 Excellent

Claribeth

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:

View our selection of featured holiday rentals in Westchester
Use the map to find apartments and other holiday homes in the Westchester neighbourhood you prefer
Enter your travel dates to view the best deals on holiday rentals in Westchester while they last

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.

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?

How many vacation rentals are there in Westchester?

What can I see and do in Westchester?

What are vacation rentals like in Westchester?