Cook County Vacation Rentals: condo and apartment rentals & more

Discover a selection of 2,000 vacation rentals in Cook County 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 private pools. Prices start at $70 per night, and condos and houses are popular options for a stay in Cook County. Either way, you'll find a rental for everyone's needs.

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Find the best place to stay — Cook County

Search 1,784 vacation rentals

Stayed May 2021

Views and more views.

This Vrbo gives a traveler everything you need and want. It is located close to great restaurants and all the different neighborhoods in Chicago. My husband and I have stayed in 5 different hotels in Chicago, this Vrbo is our only choice for future s...

Stayed Apr 2021

Great staycation

I believe this was a wonderful mini staycation for my husband and I. We had a few friends over the first night and we had an amazing time. The danger of this place is not wanting to go home when it’s check out time. It felt so good! It felt warm and ...

Stayed Apr 2021

Weekend Bachelor Party

It was a wonderful experience! The property manager (Ami) was incredibly responsive and helpful. He even offered discounted daily passes to the nearby gym, which we took him up on. The property is very spacious and slept 7 very comfortably. We all ha...

Stayed Apr 2021

Perfect spot!

This place had everything we needed for our getaway! We utilized the parking spot in the back, and loved the convenience of a 7-11 and Starbucks within a block or two. Great options for lunch/drinks within walking distance. Impeccably clean space wit...

Stayed Apr 2021

Picturesque views with all the amenities!

Well kept, clean, beautiful property with a lovely balcony that's absolutely frightening to look down from! The gym, outdoor kitchen facilities, an attached grocery store, etc. make this feel like THE place to be in Chicago! We absolutely loved our ...

Stayed Apr 2021

Perfect woodsy escape

My family rented this property for a short term rental, we needed a temporary residence while moving from out of state. Communication was excellent, house was exactly what we needed space wise, it was clean, fully stocked kitchen. The property was a...

Stayed Apr 2021

Love the Penthouse

The property is Awesome. A great balcony to stand and watch the city. The penthouse is well appointed, tasteful art, and all the things you need if you want to cook. Grand station off the red line is right there as well as a market. Uber was always a...

Stayed Apr 2021

Easter Reunion with Daughters from LA

Kai's place was perfect for our long Easter weekend. Meeting up with our daughter's from LA for the first time since Nov. of 2019. It was great to be able to cook meals to stay away from eating out, the kitchen was well equiped for all we needed. Hav...

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How many vacation rentals are available around Cook County?

Our 2021 property listings offer a large selection of 1,784 vacation rentals around Cook County. From 1,430 condo and apartment rentals to 325 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.