Discover a selection of 3,000 vacation rentals in Cook County, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $92 per night, and houses and condos are popular options for a stay in Cook County. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Cook County
Destination guide

Find the perfect vacation rental for your Cook County getaway

Learn about the unique charm of Cook County with a stay in a private vacation home. You'll find plenty to explore during your stay in the area. Navy Pier and Michigan Avenue are a couple of places to search for that perfect souvenir. Many of our vacation rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Things to do

Activities and attractions in Cook County

Are you looking for attractions to see during your stay? Venture out of your cozy vacation rental and experience everything that makes Cook County a one-of-a-kind vacation spot. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Galloping Ghost (9.8 mi / 15.8 km)
  • Adler Planetarium and Astronomy Museum (10 mi / 16.1 km)
  • Dave & Buster's (11.8 mi / 19 km)
  • Lincoln Park Zoo (13.1 mi / 21.1 km)
  • Cog Hill Golf & Country Club (13.9 mi / 22.3 km)
  • Orland Park Sportsplex (13.9 mi / 22.4 km)
Natural features

Exploring the natural features in Cook County

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Cook County is a great place to get outside. Here are some of the area’s most enchanting features, all within 30 miles (48.2 km) of the city center:

  • Millennium Park (10.7 mi / 17.3 km)
  • Abbott Park (4.1 mi / 6.6 km)
  • Midway Plaisance (6.2 mi / 10 km)
  • Jackson Park (6.8 mi / 10.9 km)
  • Burnham Park (8.1 mi / 13 km)
  • Anna and Frederick Douglass Park (8.5 mi / 13.7 km)
How to get there

How to get to and around Cook County

The nearest airport is in Chicago O'Hare Intl. Airport (ORD), located 19.7 mi (31.7 km) from the city center. If you can't find a flight that's convenient for your trip, you could also fly into Chicago Midway Airport (MDW), which is 4.2 mi (6.7 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 that serve the city. You can see more of Cook County by catching a ride on the metro at 95th Street - Longwood Station, 103rd Street Washington Heights Station or Ashland-63rd Station.

What are the top vacation rentals in Cook County?

Whether you're organizing your next great adventure with pals or a romantic getaway with your loved one, one of these top vacation rentals in Cook County is sure to attract you:

  • "Luxury Loyola 3 Bedroom, 2 Bath": This Rogers Park rental comes with 3 bedrooms and is highly rated among visitors. Amenities such as outdoor furniture and an iron and ironing board are on hand to make your stay a comfy one.
  • "Wrigleyville | Chicago Guest House | Not Just A Vacation Rental": Put your bags down and your feet up at this pick of the bunch in North Side. It features 3 bedrooms, a kitchen, coffee and tea making facilities and more.

For even more great options, use the search bar at the top of the page to find the perfect Cook County vacation rental for you.

Can I find log cabins to rent in Cook County?

Whether you're looking for a log cabin for a getaway with your besties or an adventure with the family, we have the ideal property for you. Consider one of these great stays in or near Cook County and enjoy chilling out in nature for a while:

  • "Modern Log Cabin For Luxury Experience" has all you need for a relaxing vacation, such as off-street parking options and a garden. Once you've settled in, get out and about and take in the amazing scenery.
  • Invite a couple of friends along or cozy up with your special someone at "Log Cabin On 25 Acres". Free WiFi and a barbecue grill are just some of the conveniences included at this tempting option.

What are the top-rated vacation rentals for weekend getaways in Cook County?

While extended vacations to new places are incredible, there's something undeniably lovely about heading off on a whirlwind weekend getaway. These rentals in Cook County are ideal for just that:

  • "53th Floor Magmile Penthouse - Views" - This vacation rental in Near North Side offers amenities designed to make your visit nice and comfy, such as cable/satellite TV services and a balcony. Its terrific location also makes it a good base to get out and do some sightseeing.
  • "52nd Floor Magmile Penthouse - Views" - With free WiFi and an outdoor pool, plus its convenient location in Near North Side, you wont want to leave this property.

Can I find studio apartments for rent in Cook County?

Forget about booking a boring hotel room and pick one of our studio apartments in Cook County. Here's where you can bunk down in your own digs and experience the next place you visit like a local:

  • Eat, sleep, chill with friends ... Do it all from the compact yet cleverly designed single space at "52nd Floor Magmile Penthouse - Views". Located in Near North Side, a pool table and golf are available here.
  • With lots of character and with way more privacy than a bustling hotel, "51st Floor Magmile Penthouse - Views" is another top option. It's located in River North and features a barbecue grill and WiFi.

Can I find short term rentals in Cook County?

Cook County has short-term rentals that come in all sizes, shapes and budgets. Enjoy some time out in a cheap cabin, an upmarket apartment or whatever else you like. Here are two popular options to consider:

  • Located near central Near North Side, "53th Floor Magmile Penthouse - Views" is ideal for a short-term stay. Unpack your bags and then check out all the top sights around the area.
  • "52nd Floor Magmile Penthouse - Views" also rolls out the welcome mat for short-term guests. Spend a couple of days at this option in Near North Side and discover why it's so popular with many travelers.

What are the best romantic weekend getaways in Cook County?

If you want to wow your someone special, then stay somewhere special! Organize a romantic weekend getaway in Cook County at one of these retreats and watch love bloom:

  • Unleash your inner Casanova at "Luxury Loyola 3 Bedroom, 2 Bath". This Rogers Park retreat is custom-made for romance, offering amenities like beauty services and a restaurant dining guide to help set the mood.
  • Another alluring option is "Wrigleyville | Chicago Guest House | Not Just A Vacation Rental" in North Side. Enjoy amenities here including housekeeping services and air conditioning, in addition to each other's company.

Are there mansions for rent in Cook County?

Forget waiting in turn at the hotel breakfast bar or searching for a spot in the sauna during your vacation. Round up your favorite people and give your getaway a major upgrade with one of these mansions for rent in Cook County:

  • Settle in and enjoy all the amazing things on offer at "Beautiful 9bedroom Mansion With 4 Parking Spots. Walk To Wrigley Field And Lake Michigan" in Uptown. High-end amenities here include beauty services and a firepit.
  • "Stone Mansion - 20 Free Parking Near Lake" is another outstanding option that's hard to overlook. It's located in Lake View East and comes with numerous highlights including golf and a fireplace.

What are the best houses for rent with a pool in Cook County?

In Cook County, you'll find plenty of house rentals where a pool day can be every day. Having a splashing good time will be your highest priority at one of these top-notch getaways:

  • Welcome to "Wrigleyville | Chicago Guest House | Not Just A Vacation Rental", where the first item on your must-do list should be chilling by the pool. This retreat is located in Lakeview and offers a range of family-friendly amenities, including childrens activities and a living room.
  • "New Oak Park House - 11 Mi From Downtown Chicago" in Chicago is also a hit with guests. There's so much to love about this place besides its pool, such as coffee and tea making facilities and a fridge.

What are the best large family vacation rentals in Cook County?

We've got large family vacation rentals that'll fit just about everybody — even that strange second cousin of yours! Whatever type of property you require, you'll find a perfect option on Vrbo. Here are two of our favorites in Cook County:

  • For family-friendly getaways in Lakeview, "Wrigleyville | Chicago Guest House | Not Just A Vacation Rental" is a great choice. It offers 3 bedrooms and can sleep up to 8 lucky guests. A dishwasher and books are some of the convenient amenities here.
  • "Views, Pool, Fireplace, Fitness Center" in River North is another appealing option. It has the capacity to accommodate up to 8 people and features 3 bedrooms. A fridge and a kitchen will help keep all your crew comfortable and happy.

Drag yourselves away from your comfy stay and make tracks to Orland Park Sportsplex — one of Cook County's foremost family-friendly attractions. Odyssey Fun World and Space Golf are also worth a visit while you're in the area.

Can I find family cabin rentals in Cook County?

If you've been daydreaming about a trip with the fam, book one of these cabin rentals in Cook County and give your loved ones an experience they'll never forget:

  • "Private Setting In Easy To Get To Cabin Near The Hub Of The Universe" - Located in Marion, this cozy getaway provides amenities such as a DVD player and a dishwasher.
  • "Shawnee Pines Lodging - #3 Sweet Cabin" – This option in Golconda is also a big hit with families. Conveniences here include cable/satellite TV services and a microwave oven.

For more options, use the search bar at the top of the page and adjust the filters to find the Cook County vacation rental that's perfect for your needs.

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