Where to stay near Winnetka?

Our 2020 accommodation listings offer a large selection of 170 holiday rentals near Winnetka. From 39 Houses to 89 Studios, find unique holiday homes for you to enjoy a memorable stay with your family and friends. The best place to stay near Winnetka for a long holiday or a weekend break is on HomeAway.

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:

  • The Loop: 602 holiday homes
  • West Loop: 557 holiday homes
  • Logan Square: 308 holiday homes
  • Near South Side: 662 holiday homes
  • Printers Row: 253 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? offers a large selection of holiday homes near great places in Winnetka. From travellers, the most popular points of interest to stay near are:

  • Winnetka Indian Hill Station: 1,340 holiday rentals
  • Winnetka Station: 1,331 holiday rentals
  • Chocolate Box: 1,293 holiday rentals
  • 311 S Wacker Dr: 1,416 holiday rentals
  • Wrigley Building: 1,438 holiday rentals

But there are many other points of interest around Winnetka listed on 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. offers 39 Houses in Winnetka. Our other popular types of Winnetka holiday rentals include:

  • Studios: 89 holiday houses
  • Condos/Apartments: 116 holiday houses
  • Townhouses: 5 holiday houses

Can I find a holiday accommodation with pool in Winnetka?

Yes, you can select your preferred holiday accommodation with pool among our 18 holiday homes with pool available in Winnetka. Please use our search bar to access the selection of holiday rentals available.

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