Photo by Judy Mahoney

East Side holiday rentals

We found holiday rentals — enter your dates for availability

Discover a selection of holiday rentals in East Side that are perfect for your trip. Holiday homes provide the amenities that you need and want for your family, friends or furry companion, such as a garden and pool. No matter what you're looking for, you'll be able to choose a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Frequently asked questions

How much does it cost to rent a holiday home in East Side?
A range of things can influence how much you’ll pay for a holiday home in East Side, such as the season, type of property and length of stay. But, all our holiday homes have something in common — exceptional value. Simply add your travel dates to find your home away from home.
How much does it cost to rent a beach house in East Side?
The average price for a holiday home by the beach in East Side depends on when you’re travelling and the type and size of property you want. Find prices quickly and easily on Stayz by entering your preferred travel dates and destination. Then use the filter tool to select the number of bedrooms and amenities that you need, like a pool, WiFi and air conditioning.
What are the top attractions for families in East Side?
There are plenty of cool things to see and do with the family in East Side, including:

  • Chicago Museum of Science and Industry
  • DuSable Museum of African-American History
  • 57th Street Beach

How old do you have to be to rent a holiday home in East Side?
The minimum age allowed can differ across properties on Stayz, so look at the rules of the holiday home in East Side you’re interested in. But typically, it’s 16, 18 or 21.
How long can I rent a holiday home in East Side for?
The amount of time you can rent an East Side holiday home for is down to each property. Simply enter your travel dates to see available options offering longer term stays. They come with all the things you need to make your extended holiday more enjoyable and comfortable, like kitchens and air conditioning. Some holiday homes may also offer discounted weekly or monthly prices, so you can stay even longer for less.