Destination guide

Take in the lush beauty of Winnetka

The forests and surrounding scenery provide a peaceful ambience to your holiday home in Winnetka. Renowned for its shopping, sporting events and restaurants, this city welcomes all visitors. Wrigley Field and John Hancock Center are just a couple of the must-see attractions in the area. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.


Activities and attractions in and around Winnetka

Are you looking for top things to see and do in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that Winnetka has to offer. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Skydeck Ledge (16.5 mi / 26.5 km)
  • Lincoln Park Zoo (13.9 mi / 22.4 km)
  • Navy Pier (16.2 mi / 26.1 km)
  • Wagner Farm (1.9 mi / 3.1 km)
  • Willowhill Golf Course (3.1 mi / 4.9 km)
  • The Glen Club (3.9 mi / 6.3 km)
Natural highlights

Exploring the natural features in Winnetka

Whether you're looking for adventure or just want to spend some time taking in the scenery, Winnetka is a great place to get out in nature. These are some of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Millennium Park (16.5 mi / 26.5 km)
  • Lincoln Park (11.9 mi / 19.1 km)
  • Kent Fuller Air Station Prairie (3.3 mi / 5.3 km)
  • Gallery Park (3.7 mi / 5.9 km)
  • Chicago Botanic Garden (4 mi / 6.4 km)
  • Ravinia Park (4.2 mi / 6.8 km)
How to get there

Transport to and around Winnetka

Fly into Chicago, IL (PWK-Chicago Executive), the closest airport, located 7.6 mi (12.2 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to Chicago, IL (ORD-O'Hare Intl.), which is 11.6 mi (18.6 km) away.

If you prefer train travel, make your way to Winnetka Station or Winnetka Indian Hill Station to see more of the city.

How many holiday accommodation are available around Winnetka?

Our 2019 accommodation listings offer a large selection of 239 holiday rentals around Winnetka. From 43 Houses to 176 Condos/Apartments, find unique holiday homes for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay around Winnetka is on Stayz.

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

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 Winnetka:

  • Gold Coast: 217 holiday homes
  • Lincoln Park: 658 holiday homes
  • Sheffield Neighbors: 116 holiday homes
  • Rush & Division: 219 holiday homes
  • North Center: 190 holiday homes

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

What are the most popular points of interest and landmarks to stay near when travelling to Winnetka?

Stayz offers a large selection of holiday homes near great places in Winnetka. From Stayz travellers, the most popular points of interest to stay near are:

  • Winnetka Station: 1,535 holiday rentals
  • Chocolate Box: 1,559 holiday rentals
  • Winnetka Indian Hill Station: 1,562 holiday rentals
  • Swedish Covenant Hospital: 1,677 holiday rentals
  • Lake County Fairgrounds: 115 holiday rentals

But there are many other points of interest around Winnetka listed on Stayz where you can find your place to stay. Please use our search bar to access the selection of holiday rentals available near the point of interest of your choice.

Can I rent Houses in Winnetka?

Yes, of course. Stayz offers 43 Houses in Winnetka. Our other popular types of Winnetka holiday rentals include:

  • Condos/Apartments: 176 holiday houses
  • Townhouses: 9 holiday houses
  • Studios: 155 holiday houses

Can I find a holiday accommodation with pool in Winnetka?

Yes, you can select your preferred holiday accommodation with pool among our 15 holiday homes with pool available in Winnetka. Please use our search bar to access the selection of holiday rentals available.

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