Find Vacation Homes in Cook County, IL from $241

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Top Cities in Cook County

Vacation Homes in Cook County

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Maywood
7.8 out of 10, Good, (13)
"Nice house, spacious! Only cons are there aren’t convenient outlets in the rooms to charge your phone while laying down, the front door lock is annoying to lock each time you leave the house, and the lint trap for the dryer tears your clothes. I’d stay again though! P.S. it’s just a little far from downtown (30 minutes) if you’re mostly going out in that area the Ubers/lyfts are costly if you don’t have a rental!"
United States
Nijay C.
$226 nightly
The price is $241
Nov 12 - Nov 13
Total with taxes and fees
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Wrigley Field/Lakeview -Entire Home- Large Groups!

Lakeview
10.0 out of 10, Exceptional, (84)
"We had a fantastic experience staying here. The layout was spacious and worked perfectly for our group of 10 adults—plenty of room for everyone to relax and spread out. The home was clean, well-kept, and exactly as described. Check-in and check-out were a breeze, and the neighborhood was quiet and welcoming with easy access to public transportation, which made getting around simple. Overall, a 10/10 stay—we really enjoyed our time and would definitely book again!"
United States
Joseph H.
Wrigley Field/Lakeview -Entire Home- Large Groups!

Belmont House, Classy & Chic/walk to Wrigley Field

Lakeview
9.4 out of 10, Exceptional, (56)
"We enjoyed our stay. The rental was clean, check in was easy, property manager was a good communicator and the location is solid. Would stay again."
United States
Phil N.
Belmont House, Classy & Chic/walk to Wrigley Field

Spacious House ~3min walk WrigleyField~Free Prkg

Lakeview
9.6 out of 10, Exceptional, (27)
"Great property near Wrigley Field. Loved that it had parking available as well. Will stay there again!"
United States
Linda J.
Spacious House ~3min walk WrigleyField~Free Prkg

3-bedroom hillside property in woods with fireplace and lake view

Lemont
6.8 out of 10, (5)
"Was nice and secluded. Driveway is very steep. Not all windows had curtains. Kitchen is pretty tiny. "
United States
kim h.
$234 nightly
The price is $250
Dec 1 - Dec 2
Total with taxes and fees
3-bedroom hillside property in woods with fireplace and lake view

The Vail/House/Hot Tub/Fire pit/Tesla charger/Garage

Arlington Heights
10.0 out of 10, Exceptional, (1)
The Vail/House/Hot Tub/Fire pit/Tesla charger/Garage

Berwyn Beauty

Berwyn
10.0 out of 10, Exceptional, (31)
"Our stay was everything we wanted!! Perfect location for meeting my son who lives in the area!! The home was very nice ! My daughters and I enjoyed our time spent there very much!!"
United States
Jean S.
Berwyn Beauty

3-bedroom building in lovely Westchester with AC, WiFi. Enjoy your stay

Westchester
8.0 out of 10, Very Good, (2)
"Awesome place in a very good location (quiet neighborhood). The owner was very responsive with communication and the property was very clean & spacious! 10/10!"
United States
Chris A.
3-bedroom building in lovely Westchester with AC, WiFi. Enjoy your stay

New! Beautiful 7BD Home - Sleeps 15 + 2 Car Garage

Albany Park
New! Beautiful 7BD Home - Sleeps 15 + 2 Car Garage

Luxury Home Away From Your Home

East Garfield Park
9.0 out of 10, Wonderful, (133)
"House was very nice extremely comfortable bed"
United States
Kris B.
Luxury Home Away From Your Home

A Home Away From Home!

Calumet Heights
9.6 out of 10, Exceptional, (12)
"Great place to stay. Host responded quickly to questions. Location was good and neighbor was quite. "
United States
Marchand J.
A Home Away From Home!

Great 3 bedroom rental unit near Logan Square

Avondale
9.6 out of 10, Exceptional, (67)
"A great stay! A great location with plenty of street parking. Comfy rooms, nice little kitchen and, an over-all cozy set-up."
United States
Kenzie E.
Great 3 bedroom rental unit near Logan Square

Charming Full Modern Home+Free Parking+Fast Wi-Fi & Centrally located

Park Forest
5.4 out of 10, (3)
"Property was clean and showed well. Just as advertised. Property management was professional and congenial. "
United States
Brittany B.
Charming Full Modern Home+Free Parking+Fast Wi-Fi & Centrally located

Mayors Manor, Zen Garden Oasis, Hot Tub & Sauna in Central Chicago, 8-12 guests

Bridgeport
9.4 out of 10, Exceptional, (20)
"Place was as described and worked perfect for our stay."
United States
Timothy D.
Mayors Manor, Zen Garden Oasis, Hot Tub & Sauna in Central Chicago, 8-12 guests

4 bedrooms, 6 beds, 2 full baths, and open basement loft

2.0 star property
Skokie
10.0 out of 10, Exceptional, (12)
"Place was perfect for our needs. "
United States
Tyler K.
4 bedrooms, 6 beds, 2 full baths, and open basement loft

Cozy 4-bedroom house in adorable Evanston with WiFi, AC

2.0 star property
Evanston
9.8 out of 10, Exceptional, (19)
"Beautiful home! Just like the pictures! Very clean! "
United States
Edgar V.
Cozy 4-bedroom house in adorable Evanston with WiFi, AC

Serene 3 Bedroom Home near Downtown Homewood

Homewood
10.0 out of 10, Exceptional, (1)
"House was clean and matched the pictures. Ben was very friendly and prompt with messaging. I would stay at this house again. "
United States
Cierra L.
Serene 3 Bedroom Home near Downtown Homewood

The Wrigleyville VIP- 200 steps to Wrigley- Super Clean!

Lakeview
9.8 out of 10, Exceptional, (85)
"Beautiful property! We had an excellent time and caught some Cubs games! Wrigley is just a very short walk away! We will be a repeat customer! "
United States
Tara M.
The Wrigleyville VIP- 200 steps to Wrigley- Super Clean!

Spacious 5-bedroom house great for large groups

West Town
10.0 out of 10, Exceptional, (2)
"The property was lovely and there was plenty of space to sleep, even for a large group. I would absolutely stay here again."
United States
John M.
Spacious 5-bedroom house great for large groups

Chicago Buddha's Abode

Berwyn
10.0 out of 10, Exceptional, (3)
"Very nice"
United States
Miguel G.
Chicago Buddha's Abode
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Cook County Hotel Reviews

Find out more about Cook County

Booking Tips to Find the Best Cook County Vacation Homes


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

You can find incredible Cook County vacation homes for all types of budgets: between $241 and $250 per night. The more amenities the rental has, and its proximity to popular places, the higher the price.


What is the best time to stay in a vacation home in Cook County?

If you are looking for a great deal on your vacation home in Cook County, consider visiting in , when prices are usually cheaper.


How many vacation homes are available for rent in Cook County?

There are 642 rental houses to choose from for your trip. You’ll find holiday homes located throughout the city, near sightseeing spots, and close to local nature areas.


How do I find the best deal for a vacation home in Cook County?

Begin by entering your trip dates to see what type of Cook County rental houses are available. Use the map to zoom closer into the areas or zoom out to include more locations. Use the filters on the left side of your search results to narrow down by star rating, price, number of bedrooms, amenities, and more—Expedia makes it easy to score the best deal for your budget.


Why should I rent a vacation home in Cook County?

Booking Cook County vacation home rentals is the perfect way to spend a vacation because of the privacy, variety of amenities, and comfort you’ll have in your own space.


What amenities are available in a private vacation home?

When thinking about what you want in your Cook County rental house, dream big! Depending on your budget and the area, you’ll find amenities like a private pool, hot tub, free parking, fully-equipped kitchen, in-home washer and dryer, Wi-Fi, and a beautiful view or easy access to local sightseeing spots. You can even filter your search results by accessibility to ensure that everyone in your party will be comfortable.


Why should I book a vacation home with Expedia?

Expedia has some of the best selection and deals on available vacation homes in the area—and all in one place. We reward you with members points back on every booking and ensure you get the right accommodation for the best price. And you’ll save big when you bundle your travel together, like booking a car rental in Cook County along with your vacation property, into a Cook County vacation package.


Can I cancel my vacation home with Expedia?

Some accommodations are free to cancel and refundable if done so by a specific date, while others may be non-refundable. To make sure that you can get your money back on cancellations, use the “free cancellation” filter during your search. Contact our customer service portal if you need help.

Cook County Vacation Homes information

Number of reviews
563
Accommodation
642 Vacation Homes
Lowest Price
$241
Highest Price
$250

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