Where to stay around Winnetka?

Our 2019 accommodation listings offer a large selection of 186 holiday lettings near Winnetka. From 126 Flats to 111 Studios, find unique self catering accommodation 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 accommodations for a long holiday or just a weekend break in Winnetka:

  • Chicago Loop: 437 holiday homes
  • Ukrainian Village: 240 holiday homes
  • Near West Side: 262 holiday homes
  • Lakeview: 283 holiday homes
  • Ravenswood: 84 holiday homes

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

What are the most popular points of interest and landmarks to stay near when travelling to Winnetka?

HomeAway offers a large selection of holiday accommodations near great places in Winnetka. From HomeAway travellers, the most popular points of interest to stay near are:

  • Winnetka Station: 1,004 holiday lettings
  • Glencoe Hubbard Woods Station: 995 holiday lettings
  • Winnetka Indian Hill Station: 1,011 holiday lettings
  • Alexian Brothers Medical Center: 638 holiday lettings
  • Stage 773: 1,095 holiday lettings

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

Can I rent Flats in Winnetka?

Yes, of course. HomeAway offers 126 Flats in Winnetka. Our other popular types of Winnetka holiday rentals include:

  • Studios: 111 self catering accommodations
  • Houses: 41 self catering accommodations
  • Townhouses: 7 self catering accommodations

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)

    Explore destinations around Winnetka

    Chicago
    1,115 holiday rentals
    Villa Park
    78 holiday rentals
    Gurnee
    40 holiday rentals
    Lincolnshire
    28 holiday rentals
    Evanston
    782 holiday rentals
    Lake Bluff
    18 holiday rentals
    Oak Park
    936 holiday rentals
    Schaumburg
    51 holiday rentals
    Highland Park
    38 holiday rentals
    Riverside
    504 holiday rentals
    Northbrook
    84 holiday rentals
    Des Plaines
    163 holiday rentals
    Elk Grove Village
    60 holiday rentals
    Wilmette
    367 holiday rentals
    Maywood
    532 holiday rentals
    Glencoe
    66 holiday rentals
    Hillside
    115 holiday rentals
    Libertyville
    47 holiday rentals
    Buffalo Grove
    47 holiday rentals
    Mundelein
    58 holiday rentals