Search Resorts in Westchester

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Resorts in Westchester

Eaglewood Resort and Spa

4.0 star property
8.6 out of 10, Excellent, (1006)
"Good clean resort "
The price is AED 479
AED 605 total
includes taxes & fees
22 Jun - 23 Jun
Eaglewood Resort and Spa

Hilton Chicago/Oak Brook Hills Resort & Conference Center

4.0 star property
8.6 out of 10, Excellent, (1003)
"Love it !!! ❤️"
The price is AED 445
AED 555 total
includes taxes & fees
29 Jun - 30 Jun
Hilton Chicago/Oak Brook Hills Resort & Conference Center
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.
Save an average of 15% on thousands of hotels when you're signed in

Frequently asked questions

What can I expect from a resort vacation in Westchester?
Longing for a relaxing getaway? Treat yourself to the luxuries and comforts of a resort, where you can find everything you need for your vacation from convenient food and drink options to activities and entertainment. There are 42 resorts in the area, giving you a variety of options that might have the great restaurants or blissful spa treatments you're looking for.
What's the best resort for my stay in Westchester?
Here are our top-rated resorts around Westchester: Eaglewood Resort and Spa - Spa resort. 11 mi (17.8 km) from Westchester. Features 2 restaurants, 2 bars, and a golf course. Hilton Chicago/Oak Brook Hills Resort & Conference Center - Spa resort. 5.1 mi (8.3 km) from Westchester. Has 4 restaurants, 2 bars, and a golf course. Highly rated for its pool.
What can I do in Westchester?
Travelers enjoy the shopping and other activities in Westchester, and also have good things to say about the dining options here. Galloping Ghost offers fun for the whole family, while Wrigley Field is one of the most popular places to visit nearby. You'll also find top attractions like Michigan Avenue and Soldier Field in the area.
What's the seasonal weather like in Westchester?
The hottest months are usually July and August with an average temp of 71°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Westchester are January, November, February, and December, with each month seeing an average of 5 inches of snowfall.
What's the best way to get to and around Westchester?
Fly into Chicago Midway Airport (MDW), which is located 8.4 mi (13.4 km) from the city center. Otherwise, you can search for flights to Chicago O'Hare Intl. Airport (ORD), which is 8.9 mi (14.3 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.