Photo by Jess Rigdon

Roscoe Village holiday rentals

We found 281 holiday rentals — enter your dates for availability

Discover a selection of 13 apartments and other holiday rentals in Roscoe Village that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday rentals have the best amenities for spending time at your holiday home, which might include Wi-Fi and a pool. Whatever you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

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

What is the most popular type of holiday home accommodation in Roscoe Village?
According to our research, apartments are the most sought-after type of holiday property in Roscoe Village. But as you know, everyone’s idea of an epic stay differs. Stayz has holiday homes of all shapes, sizes and budgets, and we’ll help you locate the best fit for your needs.
How much does it cost to rent a holiday home in Roscoe Village?
Season, property type and length of stay are some things that can determine the price of a holiday home. Simply click on your travel dates to find the ultimate escape. From comfy cabins to sprawling luxury villas, all Stayz holiday homes offer unbeatable value.
How much does it cost to rent a beach house in Roscoe Village?
When you travel and the style and size of the property will influence how much you’ll pay for your beachside holiday home. Enter your Roscoe Village travel dates to view your available options on Stayz. Did someone just say “private pool”? Use the filters to choose the features and amenities you want in your home.
Are there pet-friendly holiday homes in Roscoe Village?
Yes. You’ll have your pick of 10 holiday homes that cater to pets in Roscoe Village. Many of our pet-friendly holiday homes even have a backyard for your four-legged fur baby to have fun in, complimentary treats, doggie beds and proximity to parks or green space. Apply the “Pets allowed” filter to find your pawfect place on Stayz.
What are popular home amenities in Roscoe Village?
Some of the most popular home amenities people are searching for in Roscoe Village include a barbecue grill, a garden and a fireplace. Whether you’re travelling with family, pals or even pets, Stayz holiday properties have the best amenities for fun and relaxation with the people you love.
Are there large group holiday homes in Roscoe Village?
With seven Roscoe Village holiday homes that can sleep five or more people, you can invite a few extra family members or friends along. Whether you’re planning an informal gathering or a special event, Stayz will help you book the ideal space to match the occasion.
Are there holiday homes in Roscoe Village that welcome kids?
Gather the whole crew for a fun-packed adventure in Roscoe Village at one of our 10 family-friendly holiday homes. A lot of these stays come with amenities that are ideally suited to getaways with children, like laundries, living rooms and outdoor spaces. Simply click on the “Properties good for families” filter and select your favourite.
What are the top attractions for families in Roscoe Village?
Keep the kids occupied at these top family-friendly attractions in Roscoe Village:

  • Navy Pier
  • Chicago Riverwalk
  • Shedd Aquarium

Can I find two-bedroom holiday homes in Roscoe Village?
Roscoe Village has five two-bedroom holiday properties that you can choose from. Go for a holiday home with all the comfort and space you want at a price that won’t break the bank on Stayz.
Are there holiday homes with WiFi in Roscoe Village?
You’ll have a choice of three holiday homes with WiFi in Roscoe Village. If you want to disconnect from daily life on your holiday, but still need to be connected to the internet, these getaways have just what you need. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in Roscoe Village?
Roscoe Village has nine holiday homes where you can relax in air-conditioned comfort. To find a property on Stayz with this perk, choose your travel dates and use the filter tool to select the “air conditioning” box.
How old do you have to be to rent a holiday home in Roscoe Village?
You should check with the Roscoe Village holiday home you’d like on Stayz as the age limit varies. However, it’s typically 16, 18 or 21.
How long can I rent a holiday home in Roscoe Village for?
The amount of time you can book a Roscoe Village holiday home for depends on the property. Just tap in your travel dates to browse options that offer long-term stays. They have all you need to make your extended break more enjoyable and comfortable, such as kitchens and yards. Some holiday homes might also offer weekly or monthly discounts, so you can stay longer for less money.

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