Westchester Vacation Rentals, Chicago: house rentals & more

Discover a selection of 5 homes and other vacation rentals in Westchester that are perfect for your trip. Whether you’re staying in a vacation home with friends, family, or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a garden. Whatever you're looking for, you'll be sure to find a rental that has what everyone needs, including a place that is accessible or non-smoking.

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Find the best place to stay - Westchester

Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking

Sleeps 5 · 2 bedrooms · 2 bathrooms

Cozy One Bedroom, Washer Dryer, Central Location, Fireplace, Monthly Discounts

Sleeps 4 · 1 bedroom · 1 bathroom

Top rated rentals - Westchester

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All the privacy of home
Enjoy full kitchens, laundry, pools, yards and more
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More space, more privacy, more amenities — more value
A place for everyone
We stand for diversity, inclusion and families everywhere.
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Head to the charming city of Westchester

Experience the unique character of Westchester with a stay in a vacation home rental. Travelers like the basketball games, shopping and restaurants in this romantic and welcoming city. Wrigley Field and Grant Park are just a couple of the must-sees in the area. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Westchester

Do you want to find attractions to visit while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that Westchester has to offer. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

Oak Brook Golf Course (2.6 mi / 4.1 km)
TopGolf Chicago (11 mi / 17.8 km)
Seven Bridges Golf Club (11.3 mi / 18.2 km)
Cog Hill Golf & Country Club (12.8 mi / 20.6 km)
Lincoln Park Zoo (13.6 mi / 21.9 km)
Cantigny Golf Club (14.1 mi / 22.7 km)

Exploring the natural features in Westchester

Whether you're an outdoor enthusiast or just want to take in the scenery, Westchester is a great spot to appreciate mother nature. Here are some of the area’s most eye-catching sights, all within 30 miles (48.2 km) of the city center:

Grant Park (13.5 mi / 21.7 km)
Millennium Park (13.5 mi / 21.7 km)
Norridge Park District (8.6 mi / 13.9 km)
Garfield Park (8.7 mi / 14 km)
Garfield Park Conservatory (8.8 mi / 14.1 km)
Morton Arboretum (9 mi / 14.5 km)

Traveling to and around Westchester

The nearest airport is in Chicago Midway Airport (MDW), located 8.4 mi (13.4 km) from the city center. If you can't find a flight that's convenient for your trip, you can also fly into Chicago O'Hare Intl. Airport (ORD), which is 8.9 mi (14.3 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Westchester?

The most in-demand types of vacation rentals in Westchester are houses. Prefer something different? Vrbo has many options to match our guests' unique requirements, so you'll see vacation homes in all sizes and shapes. The perfect home away from home is waiting for you — get yours today.

How much does it cost to rent a vacation rental in Westchester?

A number of factors can determine what you'll pay for a vacation rental in Westchester, like the length of stay, type of property and season. But, all our vacation homes have something in common — amazing value. Simply enter your travel dates to find your perfect fit.

How much does it cost to rent a beach house in Westchester?

When you travel and the size and style of the property will influence how much you'll pay for your beachside stay. Enter your Westchester travel dates to view your available options on Vrbo. Can't live without a hot tub, or maybe a private pool? Use our filters to select the features and amenities you want.

What are popular rental amenities in Westchester?

The most popular rental amenities people are looking for in Westchester include a fireplace, off-street parking options and a pool table. Whether you're hitting the road with pals, family or even pets, Vrbo vacation rentals include the best amenities for fun and relaxation with the people that matter most.

What are the top attractions for families in Westchester?

Keep the kids entertained at these fantastic family-friendly attractions in Westchester:

Brookfield Zoo
Parkway Bank Park Entertainment District
Galloping Ghost

How old do you have to be to rent a vacation rental in Westchester?

The minimum age is typically 16, 18 or 21. It can differ from one property to another on Vrbo, so check the rules of your chosen Westchester stay before booking your stay.

How long can I rent a vacation rental in Westchester for?

The length of time you can book a vacation rental in Westchester is down to the property. Simply enter your preferred travel dates to view a list of options offering extended stays. With a range of creature comforts such as washing machines and kitchens, as well as some offering weekly or monthly discounted prices, you're sure to find someplace just right to call your home away from home in Westchester.