Where to stay around Old Town?

Our 2018 property listings offer a large selection of 133 vacation rentals near Old Town. From 70 apartments to 29 houses, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Old Town for a holiday or a weekend are on HomeAway.

What is the best area to stay when traveling to Old Town?

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 Old Town:

  • Chicago Loop: 159 vacation rentals
  • Wrigleyville: 115 vacation rentals
  • Lakeview: 211 vacation rentals
  • Gold Coast: 144 vacation rentals
  • Wicker Park: 116 vacation rentals

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

What are the popular points of interest near where I can stay when traveling to Old Town?

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

  • Royal George Theater: 1,014 vacation rentals
  • Steppenwolf Theatre: 1,014 vacation rentals
  • Legacy Motors Automotive Art Gallery: 1,010 vacation rentals
  • Chicago Water Tower: 1,008 vacation rentals
  • Wrigley Field: 1,008 vacation rentals

But there are many other points of interest around Old Town listed on HomeAway 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 apartments in Old Town?

Yes, of course. HomeAway has 70 apartments in Old Town. Our other popular types of vacation rentals in Old Town include:

  • Houses: 29 rentals available
  • Condos: 27 rentals available
  • Studios: 2 rentals available

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

Can I rent downtown rentals in Old Town?

Absolutely, HomeAway has 30 downtown rentals in Old Town. You have also many other possibilities in Old Town area, including:

  • Golf resort rentals: 23 rentals
  • Lake rentals: 7 rentals
  • Waterfront rentals: 5 rentals

Please use our search bar to access the selection of vacation rentals.

Can I find a vacation rental with pool in Old Town?

Yes, you can select your preferred vacation rental with pool among our 6 vacation rentals with pool available in Old Town. Please use our search bar to access the selection of vacation rentals available.

    The Lakeside Setting of Old Town is Ready to Explore

    The area's history and museums are just some of the reasons to vacation in Old Town. This city is walkable and welcoming, recognized for its pubs, zoo and restaurants. Top attractions in the area include John Hancock Center, Millennium Park and Willis Tower. Why not consider a vacation rental for your family holiday, romantic stay or friends trip? Many rentals offer more space along with kitchens and Internet access.