Oakland, Chicago, IL, USA

Oakland, Chicago, IL, USA

We found 16 holiday rentals — enter your dates for availability


Find the best place to stay — Oakland

Where to stay around Oakland?

Our 2018 accommodation listings offer a large selection of 16 holiday lettings near Oakland. From 6 houses to 4 apartments, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends. The best place to stay near Oakland for a long holiday or a weekend break is on HomeAway.

What is the best area to stay when travelling to Oakland?

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 Oakland:

  • Chicago Loop: 199 holiday homes
  • Ukrainian Village: 61 holiday homes
  • Near West Side: 249 holiday homes
  • Roscoe Village: 93 holiday homes
  • Ravenswood: 51 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 Oakland?

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

  • Stage 773: 887 holiday lettings
  • Chicago 87th Street Station (Woodruff): 849 holiday lettings
  • Wrigley Field: 886 holiday lettings
  • Chicago Water Tower: 881 holiday lettings
  • Auditorium Building and Theatre: 885 holiday lettings

But there are many other points of interest around Oakland 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 houses in Oakland?

Yes, of course. HomeAway offers 6 houses in Oakland. Our other popular types of Oakland holiday rentals include:

  • Apartments: 4 self catering accommodations
  • Condos: 2 self catering accommodations