Westchester holiday accommodation, Chicago: holiday houses & more

Discover a selection of 5 homes and other holiday rentals in Westchester that are perfect for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll find the amenities that you need and want, which might include Wi-Fi and a hot tub. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

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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

Perfect place for our visit

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Head to the charming city of Westchester

Learn about the unique charm of Westchester with a stay in a holiday home rental. Travellers especially 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-see attractions 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 discover top things to see and do while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that Westchester has to offer. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

Oak Brook Golf Course (2.6 mi / 4.1 km)
The Dome at the Parkway Bank Sports Complex (9.1 mi / 14.6 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)
Dave & Buster's (13.3 mi / 21.4 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 place to get outside. These are some of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

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)

Travelling to and around Westchester

The nearest airport is in Chicago Midway Airport (MDW), located 8.4 mi (13.4 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Chicago O'Hare International Airport (ORD), which is 8.9 mi (14.3 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Westchester?

The most in-demand types of holiday homes in Westchester are houses. Prefer something different? Vrbo has many options to match our guests' unique requirements, so you'll see holiday 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 holiday home in Westchester?

A number of factors can determine what you'll pay for a holiday home in Westchester, like the length of stay, type of property and season. But, all our holiday 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 home amenities in Westchester?

The most popular home 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 holiday homes 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 holiday home 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 holiday home in Westchester for?

The length of time you can book a holiday home 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.