Where to stay around Oak Street?

Our 2019 property listings offer a large selection of 1,337 vacation rentals near Oak Street. From 190 Houses to 1,081 Condos/Apartments, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Oak Street for a holiday or a weekend are on HomeAway.

What is the best area to stay near Oak Street?

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 near Oak Street:

  • Chicago Loop: 580 vacation rentals
  • Wrigleyville: 343 vacation rentals
  • Wicker Park: 568 vacation rentals
  • Lakeview: 322 vacation rentals
  • Gold Coast: 186 vacation rentals

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

Can I rent Houses near Oak Street?

Yes, of course. HomeAway has 190 Houses near Oak Street. Our other popular types of vacation rentals near Oak Street include:

  • Condos/Apartments: 1,081 rentals available
  • Cabins: 4 rentals available
  • Cottages: 4 rentals available

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

Can I find a vacation rental with pool near Oak Street?

Yes, you can select your preferred vacation rental with pool among our 97 rentals with pool available near Oak Street. Please use our search bar to access the selection of vacation rentals available.

    Can I book a vacation rental directly online or instantly near Oak Street?

    Yes, HomeAway offers a selection of 1,337 vacation rentals to book directly online and 956 with instant booking available near Oak Street. Don't wait, have a look at our vacation rentals via our search bar and be ready for your next trip near Oak Street! 

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