Destination guide

Why people love visiting charming Westchester

Learn about the unique charm of Westchester with a stay in a holiday home rental. Revered for its basketball games, shopping and restaurants, this city is both romantic and welcoming. Willis Tower and Skydeck Ledge are just a couple of the must-see attractions in the area. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.


Activities and attractions in and around Westchester

Are you hoping to discover attractions to visit during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that Westchester has to offer. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Skydeck Ledge (13.5 mi / 21.8 km)
  • Brookfield Zoo (3.3 mi / 5.4 km)
  • Lincoln Park Zoo (14.4 mi / 23.2 km)
  • John G. Shedd Aquarium (14.5 mi / 23.4 km)
  • Adler Planetarium and Astronomy Museum (14.9 mi / 23.9 km)
  • Navy Pier (15 mi / 24.1 km)
Natural highlights

Exploring the natural features in Westchester

Whether you're an active traveller or just want to appreciate the scenery, Westchester is a great spot to appreciate mother nature. Here are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Millennium Park (14.1 mi / 22.7 km)
  • Grant Park (14.2 mi / 22.9 km)
  • Lincoln Park (14.8 mi / 23.8 km)
  • York Woods County Forest Preserve (1.9 mi / 3.1 km)
  • Stevenson Park (2.6 mi / 4.2 km)
  • Ty Warner Park (4.5 mi / 7.2 km)

Travelling to and around Westchester

The nearest airport is in Chicago, IL (ORD-O'Hare Intl.), located 8.8 mi (14.1 km) from the city centre. If you can't find a flight that's convenient for your trip, you might consider flying into Chicago, IL (MDW-Midway Intl.), which is 9 mi (14.5 km) away.

Where to stay near Westchester?

Our 2019 accommodation listings offer a large selection of 120 holiday rentals near Westchester. From 37 Houses to 4 Bungalows, find unique holiday homes for you to enjoy a memorable stay with your family and friends. The best place to stay near Westchester for a long holiday or a weekend break is on HomeAway.

What is the best area to stay when travelling to Westchester?

Whether you are travelling solo or with family and friends, here are the areas with the largest selection of holiday rentals for a long holiday or just a weekend break in Westchester:

  • Chicago Loop: 488 holiday homes
  • Old Town: 189 holiday homes
  • Lakeshore East: 65 holiday homes
  • Near West Side: 260 holiday homes
  • West Rogers Park: 39 holiday homes

For other neighbourhoods, please use our search bar to access the selection of holiday homes available.

Can I rent Houses in Westchester?

Yes, of course. HomeAway offers 37 Houses in Westchester. Our other popular types of Westchester holiday rentals include:

  • Bungalows: 4 holiday houses
  • Cabins: 4 holiday houses
  • Cottages: 4 holiday houses

But you can also enjoy a great stay in one of our other holiday rentals including Studios and more.

Can I find a holiday accommodation with pool in Westchester?

Yes, you can select your preferred holiday accommodation with pool among our 10 holiday homes with pool available in Westchester. Please use our search bar to access the selection of holiday rentals available.