Discover a selection of 208 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 kitchens. Prices start at $89 per night, and houses and studios are popular options for a stay in Winnetka. Either way, you'll find a rental for everyone's needs.
AsyncDestinationUrgency
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
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 208 vacation rentals around Winnetka. From 39 house rentals to 123 studio vacation 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: 253 vacation rentals
  • Chicago Loop: 249 vacation rentals
  • Lake View: 204 vacation rentals
  • Lincoln Park: 355 vacation rentals
  • Logan Square: 257 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 Station: 1,067 vacation rentals
  • Winnetka Indian Hill Station: 1,077 vacation rentals
  • Chocolate Box: 1,067 vacation rentals
  • Maple Street Beach: 1,063 vacation rentals
  • Wrigley Field: 1,131 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 39 Houses in Winnetka. Our other popular types of vacation rentals in Winnetka include:

  • Studios: 123 rentals available
  • Condos/Apartments: 125 rentals available
  • Hotels: 9 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 preferred vacation rental with pool among our 10 vacation rentals with pool available in Winnetka. Please use our search bar to access the selection of vacation rentals available.

    Explore destinations around Winnetka

    Chicago
    1,223 vacation rentals
    Oakbrook Terrace
    230 vacation rentals
    Evanston
    605 vacation rentals
    Libertyville
    91 vacation rentals
    Forest Park
    875 vacation rentals
    Oak Park
    857 vacation rentals
    Downers Grove
    194 vacation rentals
    Northbrook
    161 vacation rentals
    Des Plaines
    338 vacation rentals
    Lombard
    233 vacation rentals
    Bloomingdale
    220 vacation rentals
    Lincolnshire
    81 vacation rentals
    Oak Brook
    237 vacation rentals
    Barrington
    175 vacation rentals
    Elk Grove Village
    149 vacation rentals
    Wheeling
    167 vacation rentals
    Glen Ellyn
    203 vacation rentals
    Arlington Heights
    186 vacation rentals
    Downers Grove Township
    268 vacation rentals
    Addison
    265 vacation rentals