Skokie holiday rentals

We found 1,919 holiday rentals — enter your dates for availability

Discover a selection of 16 homes and other holiday rentals in Skokie that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday rentals have the amenities that you expect for your stay, such as air conditioning and Wi-Fi. At the end of the day, you'll be sure to find a property to rent that has what everyone 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

The friendly area of Skokie awaits your stay

The gardens and other outdoor surroundings create an inviting atmosphere in Skokie. This welcoming city is known for its shopping, restaurants and sporting events. Wrigley Field and Michigan Avenue are just a couple of the must-see attractions in the area. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Skokie

Are you searching for top things to see and do while you're in town? Venture out of your cosy holiday rental and experience everything that makes Skokie a fun spot to go on holiday. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • The Glen Club (6 mi / 9.6 km)
  • The Dome at the Parkway Bank Sports Complex (7.7 mi / 12.3 km)
  • Northbrook Sports Complex (8.3 mi / 13.3 km)
  • Lincoln Park Zoo (9.5 mi / 15.3 km)
  • Chevy Chase Country Club (12.6 mi / 20.2 km)
  • Arlington International Racecourse (14.1 mi / 22.7 km)

Exploring the natural landscape of Skokie

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Skokie. Here are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Millennium Park (12 mi / 19.3 km)
  • Grant Park (12.6 mi / 20.3 km)
  • Portage Park (5.5 mi / 8.8 km)
  • Kathy Osterman Beach (5.6 mi / 9 km)
  • Montrose Beach (7 mi / 11.2 km)
  • Lincoln Park (8 mi / 13 km)

Transport options to and around Skokie

The nearest airport is in Chicago O'Hare International Airport (ORD), located 9.2 mi (14.8 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Chicago, IL (PWK-Chicago Executive), which is 10 mi (16 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Skokie?
According to our research, condos are the most sought-after type of property in Skokie. But of course, everyone’s idea of the perfect stay isn’t going to be the same. Stayz has holiday homes with every size, shape and budget in mind, so you’re bound to find your perfect match.
How much does it cost to rent a holiday home in Skokie?
Length of stay, property type and time of year are some of the conditions that can affect the price of a holiday home. Simply click on your travel dates to find your dream escape. From cosy chalets to expansive villas, all Stayz holiday homes offer incredible value.
How much does it cost to rent a beach house in Skokie?
When you travel and the style and size of the property will influence how much you’ll pay for your beachside escape. Put in your Skokie travel dates to see all your options on Stayz. Looking for basics like WiFi, or perks like a private pool? Use the filters to pick the amenities and features you want.
Are there pet-friendly holiday homes in Skokie?
Pack a suitcase and a bone for your pooch because Skokie has nine stays that roll out the welcome mat to doggie guests. Let your four-legged buddy have fun with the family at one of our pet-friendly holiday homes on Stayz. Simply enter your dates then check the “Pets allowed” filter box.
Can I rent a house with a pool in Skokie?
Dig out your swimsuit and inflatable unicorn, because there are two houses with a private pool in Skokie. Kick back at one of these terrific holiday homes and enjoy a pool day every day. Simply enter your dates into Stayz, then use the “pool” filter to find the ideal place for a splashing good time!
What are popular home amenities in Skokie?
When it comes to home amenities that people are on the lookout for in Skokie, a barbecue grill, a firepit and a swimming pool rank the highest. With Stayz holiday homes, you’ll find options to match your style and taste, whether you’re going on a holiday with friends, relatives or even pets.
Are there large group holiday homes in Skokie?
Yes, there are two properties in Skokie that can sleep five or more guests. From family get-togethers to events like birthday parties, these stays have ample room to hang out with your favourite people.
Are there holiday homes in Skokie that welcome kids?
Skokie has nine family-friendly holiday homes. And discovering a stay that welcomes children is a cinch with our “Properties good for families” filter. In addition to having the whole place to yourselves, you’ll also enjoy access to perks and conveniences like extra bedrooms, kitchens and yards.
What are the top attractions for families in Skokie?
There are lots of fabulous things to see and do with the family in Skokie, such as:

  • Parkway Bank Park Entertainment District
  • Montrose Beach
  • Kohl Childrens Museum

Are there one-bedroom holiday homes in Skokie?
Yes, Skokie has two one-bedroom homes available. Often positioned in prime spots because of their compact size, a one-bedroom property is ideal if you’re getting away with your partner or a pal. And with comforts such as kitchens and more privacy than a standard hotel, you’ll be able to kick back while discovering this terrific destination.
Can I find two-bedroom holiday homes in Skokie?
Skokie has five two-bedroom holiday properties to select from. Find a holiday home with all the comfort and space you’re looking for at a price that’s hard to resist on Stayz.
Are there holiday homes with WiFi in Skokie?
Pick from five holiday homes with WiFi in Skokie. If you want to disconnect from the world during your trip, but still need to be connected to the internet, these getaways have what you need. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in Skokie?
Skokie has nine holiday homes where you’ll be able to relax and recharge in air-conditioned comfort. To find a property on Stayz with this perk, enter your desired travel dates and use the handy filter tool to select the “air conditioning” box.
How old do you have to be to rent a holiday home in Skokie?
The minimum age can differ across properties on Stayz, so be sure to check the rules of the holiday home in Skokie you’re considering. But typically, it’s 16, 18 or 21.
How long can I rent a holiday home in Skokie for?
The amount of time you can book a Skokie holiday home for depends on the property. Simply enter your travel dates to browse options offering extended stays. They include all you need to make your extended trip more convenient and enjoyable, such as kitchens and laundries. Some Stayz holiday homes may also offer weekly or monthly discounted prices, so you can stay even longer for less.

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