Where to stay around Winnetka, IL?

Our 2019 property listings offer a large selection of 239 vacation rentals near Winnetka. From 122 Condos/Apartments to 107 Studios, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Winnetka for a holiday or a weekend are on VRBO.

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

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Winnetka:

  • Lakeview: 301 vacation rentals
  • Chicago Loop: 704 vacation rentals
  • Streeterville: 203 vacation rentals
  • Old Town: 236 vacation rentals
  • Wrigleyville: 326 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

Can I rent Condos/Apartments in Winnetka?

Yes, of course. VRBO has 122 Condos/Apartments in Winnetka. Our other popular types of vacation rentals in Winnetka include:

  • Studios: 107 rentals available
  • Hotels: 57 rentals available
  • Houses: 39 rentals available

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

Can I find a vacation rental with pool in Winnetka?

Yes, you can select your prefered vacation rental with pool among our 48 vacation rentals with pool available in Winnetka. Please use our search bar to access the selection of vacation rentals available.

    Take in the lush beauty of Winnetka

    The forests and surrounding scenery provide a peaceful ambiance to your vacation 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-sees in the area. If you need more space to accommodate a family vacation or friends trip, 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 vacation 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 center:

    • 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 center:

    • 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)