Cook County holiday homes

We found 4,146 holiday rentals — enter your dates for availability

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July 2025

August 2025

Discover a selection of 1126 homes, 2509 apartments and other holiday rentals in Cook County that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday homes have the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a pool. You'll be able to choose a property to rent for everyone's needs, including places that are non-smoking or accessible.

Popular Cook County destinations on Bookabach

Holiday rentals with weekly discounts - Cook County

Showing deals for:3 Oct - 10 Oct

Excellent

(16 reviews)

Comfort/Clean!: Free Parking 15 min ORD/Downtown3

Chicago, IL

20% off

NZ$187 per night

includes taxes & fees

Wonderful

(12 reviews)

Private Romantic 2 Bedroom suite in the beautiful and historic Beverly community

Chicago, IL

7% off

NZ$238 per night

includes taxes & fees

Exceptional

(8 reviews)

Cozy & Lavish 2B/1B in Homewood! 5 min from Shopping, Expressway, & New Casino!!

Homewood, IL

8% off

NZ$282 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Cook County

Showing deals for: 2 Oct - 5 Oct

Cozy 3-bedroom house in family-oriented Melrose Park.

Sleeps 6 · 3 bedrooms · 1+ bathroom

for 3 nights, 1 home

NZ$358 per night

includes taxes & fees

Game Room + Outdoor BBQ Grill | LCP Collection

Sleeps 8 · 4 bedrooms · 1+ bathroom

for 3 nights, 1 home

NZ$685 per night

includes taxes & fees

Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking

Sleeps 5 · 2 bedrooms · 2 bathrooms

for 3 nights, 1 apartment

NZ$368 per night

includes taxes & fees

10-15 MIN FROM O'HARE CHICAGO-LOVELY 3BEDROOMS GARDEN APARTMENT

Sleeps 8 · 3 bedrooms

for 3 nights, 1 apartment

NZ$448 per night

includes taxes & fees

"Cozy Rooms with WiFi, Fitness Room & On-Site Restaurant/Bar in Schaumburg "

Sleeps 4 · 25 bedrooms · 1 bathroom

for 3 nights, 1 home

NZ$186 per night

includes taxes & fees

Breathtaking home close to Schaumburg, Chicago

Sleeps 8 · 4 bedrooms · 4 bathrooms

for 3 nights, 1 home

NZ$831 per night

includes taxes & fees

Find the perfect holiday rental for your Cook County getaway

Learn about the unique charm of Cook County with a stay in a holiday home rental. This city has something for everyone. Michigan Avenue and Navy Pier are a couple of places to search for that perfect souvenir. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in Cook County

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

Harborside International Golf Center (6 mi / 9.7 km)
Galloping Ghost (9.8 mi / 15.8 km)
Dave & Buster's (11.8 mi / 19 km)
Ravisloe Country Club (12.3 mi / 19.7 km)
Lincoln Park Zoo (13.1 mi / 21.1 km)
Cog Hill Golf & Country Club (13.9 mi / 22.3 km)

Exploring the natural features in Cook County

Whether you're an active traveller or just want to take in the scenery, Cook County is a great place to get out in nature. These are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

Grant Park (10.2 mi / 16.4 km)
Millennium Park (10.8 mi / 17.3 km)
Marquette Park (2.1 mi / 3.4 km)
Abbott Park (4.1 mi / 6.6 km)
Washington Park (6 mi / 9.6 km)
Jackson Park (6.7 mi / 10.8 km)

How to get to and around Cook County

The nearest airport is in Chicago Midway Airport (MDW), located 4.2 mi (6.7 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Chicago O'Hare International Airport (ORD), which is 19.7 mi (31.7 km) away.

If you prefer to travel by train, Chicago Ashburn Station, Chicago Wrightwood Station and Chicago 91st Street Station (Beverly Hills) are the main stations in the city. You can get around Cook County by catching a ride on the metro at 95th Street - Longwood Station, 103rd Street Washington Heights Station or Ashland-63rd Station.

Frequently asked questions

What is the best area to stay in Cook County when booking a holiday home?

If you're planning a getaway to Cook County, Steger is one of the most desired places to stay. Whether you're looking for a condo, cabin or other property type, you'll always have the entire place to yourself.

What is the most popular type of holiday home accommodation in Cook County?

Based on our research, apartments are the most in-demand property type in Cook County. But as you know, everyone's idea of the perfect trip can differ. Bookabach has holiday homes in a variety of sizes and shapes, so you're sure to find your ideal match.

How much does it cost to rent a holiday home in Cook County?

A number of factors affect how much you'll pay for a holiday home in Cook County, including the type of property, length of stay and season. Still, all our holiday homes have something in common --- excellent value. Just enter your travel dates to find your ideal fit.

How much does it cost to rent a beach house in Cook County?

The average price for a holiday home close to the beach in Cook County depends on when you're travelling and the style and size of property you want. You can find prices quickly and easily on Bookabach by entering your travel dates. Then use our filter tool to select the number of bedrooms and amenities that you prefer, like a pool, WiFi and air conditioning.

What are popular home amenities in Cook County?

A microwave oven, a stovetop and a fridge top the list of most popular home amenities in Cook County. Whether you're planning to travel on your own, with your spouse or as a family, Bookabach can help you find a holiday home that suits your tastes with all the features you need.

Are there large group holiday homes in Cook County?

Choose from 172 holiday homes in Cook County that can host 10 or more guests. Whether you're planning a holiday with extended family or an event like a party, there's enough space to get your group together under one roof.

What are the top attractions for families in Cook County?

Keeping the kids entertained during your Cook County holiday is a breeze with these fabulous family-friendly attractions:

Orland Square
Odyssey Fun World
Hollywood Casino Amphitheatre

Can I find two-bedroom holiday homes in Cook County?

Take off with your besties and enjoy total privacy and comfort in one of the 562 two-bedroom holiday properties Cook County has to offer.

Are there holiday homes with WiFi in Cook County?

Cook County has 639 holiday homes with WiFi, so you'll be able to stay connected while travelling. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming Hollywood blockbusters to scrolling social media, these Bookabach homes will keep you online.

How old do you have to be to rent a holiday home in Cook County?

The minimum required age is typically 16, 18 or 21. It can change across properties on Bookabach, so check the rules of your chosen Cook County holiday home before making a booking.

How long can I rent a holiday home in Cook County for?

It's really down to the Cook County property. To see a list of options offering extended stays, just type your dates and guest number into Bookabach's search page. You can enjoy having the whole place to yourself, along with comforts such as air conditioning, a kitchen and a backyard where the little ones can play. Keep your eyes peeled for long-term stays that offer weekly or monthly discounts.