Discover a selection of 143 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 $80 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 2020 property listings offer a large selection of 143 vacation rentals around Winnetka. From 40 house rentals to 96 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

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:

  • Near North Side: 572 vacation rentals
  • The Loop: 622 vacation rentals
  • West Town: 527 vacation rentals
  • Lakeview: 233 vacation rentals
  • Lincoln Park: 525 vacation rentals

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

What are the popular point of interests near where I can stay when traveling to Winnetka?

Vrbo offers a large selection of vacation rentals near lovely places in Winnetka. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Winnetka Indian Hill Station: 1,319 vacation rentals
  • Winnetka Station: 1,304 vacation rentals
  • Chocolate Box: 1,308 vacation rentals
  • Garfield Park: 1,425 vacation rentals
  • United Center: 227 vacation rentals

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

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: 96 rentals available
  • Studios: 72 rentals available
  • Townhouses: 4 rentals available

Can I find a vacation rental with pool in Winnetka?

Yes, you can select your preferred vacation rental with pool among our 19 vacation rentals with pool available in Winnetka. Please use our search bar to access the selection of vacation rentals available.

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