Holiday Rentals in Cook County

Change your mind

Book hotels with free cancellation

Treat yourself

Be picky

Search almost a million properties worldwide

Featured Holiday Rentals in Cook County

1 bedroom, iron/ironing board, travel cot, WiFi

"The apartment looked exactly like the pictures and was very well kept. Everything was clean and functional and we didn’t have any issues. The neighborhood is very quiet and safe and also has a target nearby for quick grocery trips. Connectivity wise, there’s a busy stop within walking distance but no train stations.The host was also very responsive and helpful. We didn’t have any trouble checking in or checking out.Overall a great experience and comfortable stay."

includes taxes & fees

4 Aug - 5 Aug

includes taxes & fees

27 Jul - 28 Jul

"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"

includes taxes & fees

27 Jul - 28 Jul

includes taxes & fees

27 Jul - 28 Jul

includes taxes & fees

18 Aug - 19 Aug

includes taxes & fees

10 Aug - 11 Aug

"Lovely little cottage in great location with excellent restaurants close by. Had everything we needed for our stay. Kitchen was perfectly equipped and having the washer dryer was such a bonus. The communication with the landlord was very good. Would absolutely stay here again. "

includes taxes & fees

23 Jul - 24 Jul

1 bedroom, iron/ironing board, free WiFi, bed sheets

"It was a great location, internet was a little spotty on streaming services but we were in walking distance to so much it was worth it "

includes taxes & fees

11 Aug - 12 Aug

includes taxes & fees

27 Jul - 28 Jul

"We stayed a few nights and everything was nice and clean. Thank you!"

includes taxes & fees

27 Jul - 28 Jul

includes taxes & fees

27 Jul - 28 Jul

"This was one of our favorite places we have ever stayed! It was clean, decorated beautifully, had comfortable beds, a refrigerator with an ice maker and filtered water, washer and dryer that worked great, a cool backyard with hammocks, and even little things like coffee creamer, toothpaste, and mouthwash in case you forgot yours. We stayed in three different rental places on our trip and this was by far our favorite! What a beautiful home! "

includes taxes & fees

23 Jul - 24 Jul

"Great location. Very walkable to restaurants and bars. Awesome park nearby. Host was easy to communicate with. "

includes taxes & fees

27 Jul - 28 Jul

"It was even better than we thought it would be!"

includes taxes & fees

4 Aug - 5 Aug

includes taxes & fees

27 Jul - 28 Jul

1 bedroom, iron/ironing board, WiFi, bed sheets

"Quiet, clean and spacious! A peaceful neighborhood. "

includes taxes & fees

24 Jul - 25 Jul

includes taxes & fees

27 Jul - 28 Jul

"We had a short stay in this property and we wished it could have been longer. The house was very nice, clean and the communication was great!! It is a short drive to the airport and to downtown. We would definitely stay here again"

includes taxes & fees

28 Jul - 29 Jul

includes taxes & fees

27 Jul - 28 Jul

Save an average of 15% on thousands of hotels when you're signed in

Top Cook County Hotel Reviews

Radisson Blu Aqua Hotel Chicago

10/10 Excellent

"It’s always a great stay at the Radisson!! "

Swissotel - Chicago

10/10 Excellent

"This hotel was great! Extremely clean; rooms were very quiet and even with the city view we had a view of the lake; central location; helpful staff; Amuse is a great little restaurant/bar in the lobby; right across the street from the stairs down to the river walk; close to Navy Pier and can walk to shopping on Michigan Ave. Perfect for our long weekend stay."

Find out more about Cook County

Holiday Homes in Cook County

Search for holiday homes in Cook County on Expedia.ie! You can easily find your home rentals, villas, holiday apartments in Cook County using one of the methods below:

View our selection of featured holiday homes in Cook County
Use the map to find apartments and other holiday rentals in the Cook County neighbourhood you prefer
Enter your travel dates to view the best deals on holiday homes in Cook County while they last

Look no further and take a look at our great range of rental properties in Cook County!

Explore a world of travel with Expedia

Popular Cook County Holiday Rentals

Chicago Holiday Rentals

Members save 10% or more on over 100,000 hotels worldwide when you’re signed in

Holiday Rentals in Cook County

Change your mind

Treat yourself

Be picky

Featured Holiday Rentals in Cook County

The One: A 1BR Stay That Feels Like Home

Sun-Drenched 1BR Apartment

Stylish 1BR in West Loop

Luxury Unit with Rooftop Lounge & Spectacular City Views

2 Connecting Suites at a 4⭐️ Hotel

2 Connecting Suites at a 5⭐️ Hotel

Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG

Cozy studio in Andersonville Chicago

Cozy Room with Rooftop Lounge & City Views in River North

A quiet stay while you are away

Spacious Room with Rooftop Lounge & Scenic Views of Chicago

Modern Suite with Rooftop Lounge & Views of Downtown Chicago

Cozy house in the city

Light-Filled 1-Bedroom Apt

Prime City Stay in a 1BR Apt

2 Spacious King Room with Rooftop Lounge & Scenic Views of Chicago

Peaceful 1BR Escape in Evanston

2 Relaxing Rooms with Rooftop Lounge & City Views of Chicago

The Comfy King Ranch - King Bed/Spacious Home/Fast WiFi/Free Parking

2 Suites with Rooftop Lounge & Beautiful Views of Chicago Skyline

Top Cook County Hotel Reviews

Radisson Blu Aqua Hotel Chicago

citizenM Chicago Downtown

The Royal Sonesta Chicago Downtown

The Wade

The Whitehall Hotel, BW Premier Collection

Hotel Felix River North/Magnificent Mile

Hilton Chicago/Magnificent Mile Suites

Swissotel - Chicago

River Hotel

Find out more about Cook County

Holiday Homes in Cook County

Explore a world of travel with Expedia