Cook County holiday rentals

We found 3,974 holiday rentals — enter your dates for availability
Discover a selection of 823 homes, 2578 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:20 Nov - 27 Nov

Room
Interior
Living area
Interior
Exceptional
(9 reviews)

Near Lakefront! Minutes from the beach, Obama museum campus and 2 golf courses!!

Chicago

7% off
AU$5,760
for 7 nights, 1 home
AU$823 per night
includes taxes & fees
Near Lakefront! Minutes from the beach, Obama museum campus and 2 golf courses!!
Dining
Interior
Living area
Living area
Exceptional
(35 reviews)

Lux Home in Chicago 7mins Downtown

Chicago

7% off
AU$6,551
for 7 nights, 1 home
AU$936 per night
includes taxes & fees
Lux Home in Chicago 7mins Downtown
Living area
Dining
Room
Outdoor dining
Exceptional
(11 reviews)

Quick Access to O'Hare and Chicago downtown

Melrose Park

8% off
AU$3,412
for 7 nights, 1 home
AU$487 per night
includes taxes & fees
Quick Access to O'Hare and Chicago downtown
Private kitchen
Exterior
Exterior
Interior
Excellent
(10 reviews)

Luxe Home 20 min from Downtown Chicago ,heated indoor pool, Spa bath, tree house

Skokie

8% off
AU$16,679
for 7 nights, 1 home
AU$2,383 per night
includes taxes & fees
Luxe Home 20 min from Downtown Chicago ,heated indoor pool, Spa bath, tree house
Interior
Living area
Living area
Room
Exceptional
(11 reviews)

Paradise 4BR w/ Pool & Games

Schaumburg

8% off
AU$4,460
for 7 nights, 1 home
AU$637 per night
includes taxes & fees
Paradise 4BR w/ Pool & Games
Room
Private kitchen
Living area
Exterior detail
Exceptional
(63 reviews)

Steps from the “L” train to Wrigley & Downtown

Chicago

7% off
AU$4,583
for 7 nights, 1 apartment
AU$655 per night
includes taxes & fees
Steps from the “L” train to Wrigley & Downtown
Interior
Interior
Interior
Dining
Exceptional
(5 reviews)

Massive Queen Anne Mansion for your whole family to stay!

Chicago

8% off
AU$14,444
for 7 nights, 1 home
AU$2,063 per night
includes taxes & fees
Massive Queen Anne Mansion for your whole family to stay!
Dining
Room
Living area
Private kitchen
Very good
(11 reviews)

South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly

Chicago

7% off
AU$2,414
for 7 nights, 1 apartment
AU$345 per night
includes taxes & fees
South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly
Patio Deck 2
Living Room
Front Yard View
Bedroom 1 (King Size) + 55Inch TV
Exceptional
(22 reviews)

Spacious 5 BR / King Size Beds + Private Parking!

Chicago

8% off
AU$9,788
for 7 nights, 1 home
AU$1,398 per night
includes taxes & fees
Spacious 5 BR / King Size Beds + Private Parking!
Interior
Private kitchen
Exterior
Interior
Exceptional
(27 reviews)

Stunning 6 BR Home * Chicago * Centrally Located

Chicago

8% off
AU$8,440
for 7 nights, 1 home
AU$1,206 per night
includes taxes & fees
Stunning 6 BR Home * Chicago * Centrally Located
Dining
Interior
Private kitchen
Living area
Exceptional
(39 reviews)

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

Berwyn

8% off
AU$2,619
for 7 nights, 1 apartment
AU$374 per night
includes taxes & fees
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Private kitchen
Kitchen and dining area.
Sun room.
Back yard patio.
Exceptional
(40 reviews)

Modern & Clean 3 Bedroom House with Sunroom

Schaumburg

8% off
AU$2,951
for 7 nights, 1 home
AU$422 per night
includes taxes & fees
Modern & Clean 3 Bedroom House with Sunroom
Living area
Interior
Dining
Interior
Exceptional
(38 reviews)

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

Chicago

7% off
AU$12,508
for 7 nights, 1 home
AU$1,787 per night
includes taxes & fees
Lincoln Park 3BR Townhome • Rooftop • King Suite • Sleeps 10
Living room area
3 bedroom unit is top floor of historic greystone
Living room area opens into dining room & kitchen
Dining room area
Exceptional
(96 reviews)

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

Chicago

7% off
AU$6,297
for 7 nights, 1 home
AU$900 per night
includes taxes & fees
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Hallway 2nd floor
Property grounds
Dining
Private kitchen
Very good
(11 reviews)

4BR family retreat -sleeps 8, minutes to Woodfield mall & O'Hare airport

Hoffman Estates

8% off
AU$3,160
for 7 nights, 1 home
AU$451 per night
includes taxes & fees
4BR family retreat -sleeps 8, minutes to Woodfield mall & O'Hare airport
Terrace/patio
Living area
Dining
Living area
Exceptional
(56 reviews)

Cozy two bedroom close to Wrigley Field

Chicago

15% off
AU$4,042
for 7 nights, 1 apartment
AU$577 per night
includes taxes & fees
Cozy two bedroom close to Wrigley Field
Bedroom #1 w 2 full size beds plus a desk
Spacious Living Room with Roku TV, sofa bed, smart thermostat, etc
7 minutes drive to downtown and Millenium Park
Private kitchen
Wonderful
(22 reviews)

1 #12 - 2 Bedroom / 1 Bath Condo near McCormick Place, Wintrust Arena, Chinatown

Chicago

7% off
AU$2,676
for 7 nights, 1 apartment
AU$382 per night
includes taxes & fees
1 #12 - 2 Bedroom / 1 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
Private kitchen
Living area
Room
Point of interest
Exceptional
(13 reviews)

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

Chicago

11% off
AU$4,834
for 7 nights, 1 home
AU$691 per night
includes taxes & fees
1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown
Interior
Interior
Dining
Private kitchen
Exceptional
(15 reviews)

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

Chicago

7% off
AU$2,697
for 7 nights, 1 apartment
AU$385 per night
includes taxes & fees
Modern + Cozy Chicago stay w/garage parking & 20min to downtown
Private kitchen
Living area
Interior
Room
Exceptional
(19 reviews)

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

Berwyn

8% off
AU$2,342
for 7 nights, 1 apartment
AU$335 per night
includes taxes & fees
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
Living area
Interior
Room
Dining
Exceptional
(24 reviews)

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

Berwyn

8% off
AU$2,314
for 7 nights, 1 apartment
AU$331 per night
includes taxes & fees
Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT
Kitchen (upstairs)
Downstairs living area
Fun Mirror Wall Upstairs
Downstairs living room
Exceptional
(98 reviews)

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

Chicago

7% off
AU$13,223
for 7 nights, 1 apartment
AU$1,889 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Private kitchen
Living area
Interior
Interior
Exceptional
(6 reviews)

The En Bronze ~ 7mins To Dining & Downtown Chicago

Chicago

7% off
AU$4,427
for 7 nights, 1 apartment
AU$632 per night
includes taxes & fees
The En Bronze ~ 7mins To Dining & Downtown Chicago
Living area
Interior
Interior
Private kitchen
Exceptional
(11 reviews)

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

Chicago

7% off
AU$2,962
for 7 nights, 1 apartment
AU$423 per night
includes taxes & fees
Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!

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)
  • 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)
  • Orland Park Sportsplex (13.9 mi / 22.4 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)
  • Midway Plaisance (5.9 mi / 9.5 km)
  • Washington Park (6 mi / 9.6 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