Discover a selection of 153 vacation rentals in Winnetka, IL that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $114 per night, and houses and condos are popular options for a stay in Winnetka. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Winnetka
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Destination guide

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

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)
Natural features

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)
How to get there

Transportation to and around Winnetka

Fly into Chicago, IL (PWK-Chicago Executive), the closest airport, located 7.6 mi (12.2 km) from the city center. 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 vacation rentals are available around Winnetka, IL?

Our 2021 property listings offer a large selection of 153 vacation rentals around Winnetka. From 40 house rentals to 109 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Houses in Winnetka?

Yes, of course. Vrbo has 40 Houses in Winnetka. Our other popular types of vacation rentals in Winnetka include:

  • Condos/Apartments: 109 rentals available
  • Studios: 79 rentals available
  • Cabins: 2 rentals available

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

Can I find a vacation rental with pool in Winnetka?

Yes, you can select your preferred vacation rental with pool among our 23 vacation rentals with pool available in Winnetka. Please use our search bar to access the selection of vacation rentals available.