Cook County holiday rentals

We found 3,987 holiday rentals — enter your dates for availability
Discover a selection of 835 homes, 2571 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 Stayz

Holiday rentals with weekly discounts – Cook County

Showing deals for:18 Dec - 25 Dec

Living area
Interior
Terrace/patio
Exterior
Exceptional
(39 reviews)

Private Historical Mansion,Luxury Home in Chicago’s Gold Coast, Event-Capable.

Chicago

8% off
AU$35,358
for 7 nights, 1 home
AU$5,051 per night
includes taxes & fees
Private Historical Mansion,Luxury Home in Chicago’s Gold Coast, Event-Capable.
Dining
Our downtown Townhouse is in an amazing location
It is huge! With lots of areas for relaxing and entertaining
Room
Exceptional
(91 reviews)

Historic luxury townhouse on Chicago's Gold Coast

Chicago

5% off
AU$10,598
for 7 nights, 1 home
AU$1,514 per night
includes taxes & fees
Historic luxury townhouse on Chicago's Gold Coast
Room
Interior
Living area
Dining
Exceptional
(40 reviews)

Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP

Berwyn

8% off
AU$2,803
for 7 nights, 1 apartment
AU$400 per night
includes taxes & fees
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Room
Cozy Home
Interior
Living area
Exceptional
(12 reviews)

Spacious 4BR Near O’Hare & Rosemont Sleeps 8 / 2 Kitchens / Free Parking

Chicago

7% off
AU$4,807
for 7 nights, 1 home
AU$687 per night
includes taxes & fees
Spacious 4BR Near O’Hare & Rosemont Sleeps 8 / 2 Kitchens / Free Parking
Interior
Interior
Private kitchen
Room
Wonderful
(88 reviews)

Chic, Cozy home, by Blue Line Train Stop + Free parking

Chicago

5% off
AU$1,742
for 7 nights, 1 apartment
AU$249 per night
includes taxes & fees
Chic, Cozy home, by Blue Line Train Stop + Free parking
Living Room with 60 in Smart TV
Chef kitchen with Sub-Zero refrigerator, Wolf stove, Bosch dishwasher.
Living Room with 60 in Smart TV
Bedroom 1 - King Bed
Exceptional
(92 reviews)

Stunning Lincoln Park Single-Family House with Fantastic Game Room

Chicago

11% off
AU$10,983
for 7 nights, 1 home
AU$1,569 per night
includes taxes & fees
Stunning Lincoln Park Single-Family House with Fantastic Game Room
Dining
Living area
Private kitchen
Exterior
Exceptional
(111 reviews)

Wrigley Field/Lakeview -Entire Home- Large Groups!

Chicago

11% off
AU$7,568
for 7 nights, 1 home
AU$1,081 per night
includes taxes & fees
Wrigley Field/Lakeview -Entire Home- Large Groups!
Room
Living area
Interior
Dining
Exceptional
(22 reviews)

Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW

Berwyn

8% off
AU$2,487
for 7 nights, 1 apartment
AU$355 per night
includes taxes & fees
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
Dining
Private kitchen
Living area
Room
Exceptional
(67 reviews)

Steps from the “L” train to Wrigley & Downtown

Chicago

7% off
AU$4,577
for 7 nights, 1 apartment
AU$654 per night
includes taxes & fees
Steps from the “L” train to Wrigley & Downtown
Private kitchen
Dining
Living area
Interior
Exceptional
(15 reviews)

Elegant Escape by Downtown Burr Ridge with an easy access to Chicago Landmarks

Burr Ridge

8% off
AU$5,378
for 7 nights, 1 home
AU$768 per night
includes taxes & fees
Elegant Escape by Downtown Burr Ridge with an easy access to Chicago Landmarks
View of Robey Hotel from back deck
3 bedroom unit is top floor of historic greystone
Living room area
Living room area opens into dining room & kitchen
Exceptional
(99 reviews)

Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.

Chicago

7% off
AU$6,288
for 7 nights, 1 home
AU$898 per night
includes taxes & fees
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Front Yard View
Living Room
Bedroom 1 (King Size) + 55Inch TV
Patio Deck 2
Exceptional
(23 reviews)

Spacious 5 BR / King Size Beds + Private Parking!

Chicago

8% off
AU$8,860
for 7 nights, 1 home
AU$1,266 per night
includes taxes & fees
Spacious 5 BR / King Size Beds + Private Parking!
Living area
Belmont Harbor
Exterior
Living area
Exceptional
(192 reviews)

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Chicago

15% off
AU$6,630
for 7 nights, 1 home
AU$947 per night
includes taxes & fees
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Dining
Living area
Living area
Private kitchen
Exceptional
(57 reviews)

Cozy two bedroom close to Wrigley Field

Chicago

15% off
AU$4,204
for 7 nights, 1 apartment
AU$601 per night
includes taxes & fees
Cozy two bedroom close to Wrigley Field
Room
Dining
Living area
Private kitchen
Wonderful
(20 reviews)

Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI

Berwyn

8% off
AU$2,429
for 7 nights, 1 apartment
AU$347 per night
includes taxes & fees
Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI
Interior
Interior
Living area
Room
Exceptional
(38 reviews)

Lincoln Park 3BR Townhome • Rooftop • King Suite • Sleeps 10

Chicago

7% off
AU$10,603
for 7 nights, 1 home
AU$1,515 per night
includes taxes & fees
Lincoln Park 3BR Townhome • Rooftop • King Suite • Sleeps 10
Dining
Living area
Interior detail
Private kitchen
Exceptional
(14 reviews)

Ridgeland Retreat/ Street level Apt easy access

Berwyn

8% off
AU$4,044
for 7 nights, 1 apartment
AU$578 per night
includes taxes & fees
Ridgeland Retreat/ Street level Apt easy access
Private kitchen
Living area
Miscellaneous
Point of interest
Exceptional
(15 reviews)

1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown

Chicago

11% off
AU$4,828
for 7 nights, 1 home
AU$690 per night
includes taxes & fees
1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown
Living area
Interior
Room
Dining
Exceptional
(24 reviews)

Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT

Berwyn

8% off
AU$2,487
for 7 nights, 1 apartment
AU$355 per night
includes taxes & fees
Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT
Interior
Interior
Private kitchen
Room
Exceptional
(18 reviews)

Modern + Cozy Chicago stay w/garage parking & 20min to downtown

Chicago

7% off
AU$2,592
for 7 nights, 1 apartment
AU$370 per night
includes taxes & fees
Modern + Cozy Chicago stay w/garage parking & 20min to downtown
Living area
Interior
Private kitchen
Room
Exceptional
(12 reviews)

Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!

Chicago

7% off
AU$2,959
for 7 nights, 1 apartment
AU$423 per night
includes taxes & fees
Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!
Living area
Exterior
Room
Living area
Exceptional
(108 reviews)

Lg Studio Apt. No cleaning fee. Obama Center 10 mins.

Chicago

8% off
AU$1,485
for 7 nights, 1 apartment
AU$212 per night
includes taxes & fees
Lg Studio Apt. No cleaning fee. Obama Center 10 mins.
Interior
Living area
Room
Interior
Exceptional
(7 reviews)

The En Bronze ~ 7mins To Dining & Downtown Chicago

Chicago

7% off
AU$4,421
for 7 nights, 1 apartment
AU$632 per night
includes taxes & fees
The En Bronze ~ 7mins To Dining & Downtown Chicago
Upstairs queen bedroom 2
Downstairs living area
Kitchen (upstairs)
Fun Mirror Wall Upstairs
Exceptional
(99 reviews)

Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!

Chicago

7% off
AU$12,255
for 7 nights, 1 apartment
AU$1,751 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!

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. Navy Pier and Michigan Avenue 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)
  • 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)
  • Oak Brook Golf Course (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:

  • Millennium Park (10.8 mi / 17.3 km)
  • Grant Park (10.2 mi / 16.4 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. Stayz 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 Stayz 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, Stayz 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 Stayz 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 Stayz, 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 Stayz'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.

More holiday ideas