Where to stay near Winnetka?

Our 2019 accommodation listings offer a large selection of 182 holiday rentals near Winnetka. From 122 Condos/Apartments to 107 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:

  • Lakeview: 296 holiday homes
  • River West: 106 holiday homes
  • Sheffield Neighbors: 116 holiday homes
  • Rush & Division: 149 holiday homes
  • West Bucktown: 82 holiday homes

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

Can I rent Condos/Apartments in Winnetka?

Yes, of course. HomeAway offers 122 Condos/Apartments in Winnetka. Our other popular types of Winnetka holiday rentals include:

  • Studios: 107 holiday houses
  • Houses: 40 holiday houses
  • Townhouses: 9 holiday houses

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

Can I find a holiday accommodation with pool in Winnetka?

Yes, you can select your preferred holiday accommodation with pool among our 9 holiday homes with pool available in Winnetka. Please use our search bar to access the selection of holiday rentals available.

    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)

    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)