Cook County vacation rentals

We found 4,159 vacation rentals — enter your dates for availability

Discover a selection of 1125 homes, 2511 apartments, and other vacation rentals in Cook County that are perfect for your trip. Whether you're traveling with a group or just with your pet, vacation homes have the best amenities for hanging out with the people that matter most, including parking and a TV. You'll be sure to find a rental to meet everyone's needs, including places that are non-smoking or accessible.

Popular Cook County destinations on Vrbo

Vacation rentals with weekly discounts - Cook County

Showing deals for:Sep 12 - Sep 19

Find out more about Cook County

Find out more about Cook County

Why visit Cook County

  1. Urban Exploration: Discover the vibrant streets of Chicago, filled with iconic landmarks and diverse neighborhoods.
  2. Outdoor Activities: Enjoy scenic parks and beautiful beaches perfect for picnics, hiking, and relaxation.
  3. Cultural Experiences: Visit art galleries and local events that showcase the rich culture of the area.
  4. Charming Neighborhoods: Explore unique shops and eateries in quaint areas like Oak Park and Skokie.
  5. Variety of Accommodations: Choose from cozy apartments, stylish condos, and inviting vacation homes for your stay.

Popular types of accommodation in Cook County

If you're planning a getaway to Cook County, you're in for a treat! Our most popular vacation rental options include cozy apartments, houses, and stylish condos. Whether you're looking for charming home rentals, spacious bedroom apartments, or inviting houses for rent, we have a variety of choices to suit your needs. Explore our rentals and find the perfect spot for your next adventure in Cook County!

  • Apartments: The top choice for visitors in Cook County, offering convenient and comfortable living spaces perfect for both short and extended stays.
  • Houses: A fantastic option for families or groups, providing spacious and personalized accommodations for a home-away-from-home experience.
  • Condos: A popular selection that combines the benefits of hotel amenities with the comfort of a private residence.
  • Cottages: Quaint and charming, these rentals offer a cozy atmosphere ideal for a relaxing getaway.
  • Caravan Parks: A unique option for outdoor enthusiasts, featuring facilities for camping and recreational vehicles in a scenic setting.**

Top attractions in Cook County

Cook County is perfect for outdoor enthusiasts, families, and city explorers alike. With a variety of popular attractions such as urban parks, beaches, and event venues, visitors can enjoy a rich mix of culture and fun. Whether you’re seeking family-friendly activities or unique city experiences, Cook County has something to offer everyone for an unforgettable vacation.

  1. Michigan Avenue: Known as the "Magnificent Mile," this vibrant street boasts a mix of high-end shops, dining, and iconic architecture. It's perfect for shopping enthusiasts and those looking to soak in the bustling city atmosphere.
  2. McCormick Place: As the largest convention center in North America, McCormick Place hosts major events and conferences, offering a unique opportunity to network and experience the business side of the city.
  3. Navy Pier: This lively pier features stunning lake views, entertainment options, and public art installations, making it a great spot for relaxation and enjoying the friendly local vibe.

Things to do recommended for couples

Experience romance in Cook County with a medieval feast at Schaumburg Medieval Times, enjoy live music at the Hollywood Casino Amphitheatre, and unwind in luxury at the Bridges of Poplar Creek Country Club. Each offers a unique vibe perfect for couples seeking memorable moments together.

Things to do recommended for families

Families visiting Cook County can catch a game at Wrigley Field for an exciting sports experience, relax at the Northerly Island Natural Area surrounded by nature, and have a blast at Odyssey Fun World, where adventure and family fun await everyone!

What do I need to keep in mind when booking a vacation in Cook County

When traveling with a group, your family, pets, or planning an extended stay, it's important to prioritize your preferences in the search. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Cook County with a group: Think about how many bedrooms you’ll require, along with features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for all these options and more on Vrbo.
  • Traveling to Cook County with young kids: Traveling with young kids can be tricky. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you'll be to family-friendly attractions.
  • Taking your pets with you to Cook County: For many families, a vacation isn’t truly fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Cook County: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include features like parking, a well-equipped kitchen, or a private pool in your search to enhance your experience.

Where to stay in Cook County

Cook County, Illinois, offers a vibrant mix of urban excitement and family-friendly activities. Explore the bustling streets of Chicago, visit the scenic parks, and enjoy art galleries that showcase local talent. Nearby neighborhoods like Oak Park and Skokie provide charming atmospheres with unique shops and eateries. Perfect for outdoor enthusiasts and city lovers alike, your vacation in Cook County promises unforgettable experiences filled with friendly faces and rich culture.

  • Chicago: As the third-largest city in the United States, Chicago offers a vibrant urban experience in Cook County. Travelers flock to this metropolis for its rich cultural heritage, diverse dining options, and stunning architecture. Explore Millennium Park, where you can see the iconic Cloud Gate sculpture, or take in a game at Wrigley Field, home of the Chicago Cubs. The city’s waterfront along Lake Michigan provides ample opportunities for outdoor activities, including biking and kayaking. With a bustling shopping scene and numerous theaters, Chicago promises an unforgettable city adventure.
  • Downtown Chicago: The heart of the city, Downtown Chicago is a dynamic neighborhood teeming with energy and attractions. This area is renowned for its skyscrapers, shopping districts, and cultural institutions. Visitors can stroll along the Chicago Riverwalk, enjoy views of the impressive architecture, and indulge in shopping along State Street and Michigan Avenue. Iconic venues like the Art Institute of Chicago and the Chicago Symphony Orchestra beckon culture enthusiasts. With its array of dining options and vibrant nightlife, Downtown Chicago offers a rich urban experience for families and city explorers alike.
  • Magnificent Mile: Known for its upscale shopping, the Magnificent Mile is a must-visit for those looking to indulge in a bit of retail therapy. This iconic stretch along Michigan Avenue is lined with luxury boutiques, department stores, and gourmet dining. Beyond shopping, the neighborhood boasts cultural attractions such as the Museum of Contemporary Art and the historic Water Tower. With its lively atmosphere and beautiful architecture, the Magnificent Mile is perfect for a leisurely day of exploration, making it an ideal spot for families and city adventurers alike.

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming travel plans? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking an extended stay for even greater savings. To discover a Vrbo property that suits your budget, take advantage of our filters to narrow your search by price, location, and type of vacation rental. We're here to help you find the perfect getaway!

Unlock savings with One Key

Reserve an eligible Vrbo for your group getaway and earn OneKeyCash™ on your reservation. It's rewarding to be the planner! When you enroll in our travel rewards program, One Key, you’ll gain immediate access to member savings and earn OneKeyCash™ on qualifying bookings. Sign up today and start enjoying your savings!

Vrbo Trips: Planning as easy as it gets

Vrbo's user-friendly Trip Board offers you a convenient way to plan your journeys. You can start new trips, pick up where you last paused, or easily review and arrange your travel plans. All the properties you've saved or booked are now categorized under Potential, Upcoming, or Current Trips. To explore the Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

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. Michigan Avenue and Navy Pier 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 for a relaxing getaway.

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:

  • Harborside International Golf Center (6 mi / 9.7 km)
  • Galloping Ghost (9.8 mi / 15.8 km)
  • Dave & Buster's (11.8 mi / 19 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)

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:

  • Grant Park (10.2 mi / 16.4 km)
  • Millennium Park (10.8 mi / 17.3 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 center. If you can't find a flight that's convenient for your trip, you could also fly into Chicago O'Hare Intl. 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 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.

Frequently asked questions

What is the best area to stay in Cook County when booking a vacation rental?
Tinley Park is among the more popular locations to find a vacation property in Cook County. Searching for some top things to see and do in this destination? Check out Hollywood Casino Amphitheatre and Credit Union 1 Amphitheatre.
What is the most popular type of vacation rental accommodation in Cook County?
Apartments are the most popular kind of vacation rental in Cook County, according to our data. Even if you’ve got a different idea about what you want, Vrbo has vacation homes in loads of shapes and sizes. Filter our options to find your perfect match.
How much does it cost to rent a vacation rental in Cook County?
A range of factors affect what you’ll pay for a vacation rental in Cook County, such as the season, length of stay and type of property. But, all Vrbo homes have one thing in common — excellent value. Simply enter your travel dates to find your ideal escape.
How much does it cost to rent a beach house in Cook County?
The average price for a vacation home by the beach in Cook County depends on when you’re traveling and the size and style of property you want. Find prices quickly and easily on Vrbo by entering your travel dates. Then use the filters to select the number of bedrooms and amenities that you need, like WiFi, a pool and air conditioning.
Are there pet-friendly vacation rentals in Cook County?
With 228 properties that welcome four-legged guests, your furry friend can join in on your Cook County getaway. Use our filter tool to browse our pet-friendly vacation rentals and find a stay that’s pawfect on Vrbo.
Are there large group vacation rentals in Cook County?
With 226 properties that can host 10 or more people in Cook County, there’s no need to hold back on your invites. From fun family get-togethers to events like weddings and birthday parties, Vrbo can help you find a large group rental to match the occasion.
What are the top attractions for families in Cook County?
There are plenty of wonderful things to do and see with the family in Cook County, including:

  • Orland Square
  • Odyssey Fun World
  • Hollywood Casino Amphitheatre

Are there one-bedroom vacation rentals in Cook County?
Yes, you can pick from 701 one-bedroom rentals in Cook County. Whether you’d prefer a cozy cottage or an upmarket condo, our one-bedroom rentals are perfect if you don’t require a lot of space. One of the major perks of having your own pad? You won’t ever need to share your getaway with strangers.
Can I find two-bedroom vacation rentals in Cook County?
You can pick from 599 two-bedroom homes in Cook County. Give the kids the second room or maybe fill it with a couple of your favorite people. There’s a comfy spot for whoever’s lucky enough to come along for the ride.
Are there vacation rentals with WiFi in Cook County?
Whether you’d like to stay in touch with the news, look over emails or surf social networks, there are 853 vacation homes with WiFi in Cook County. Check the “WiFi” box when searching on Vrbo and stay connected on your getaway.
How can I find vacation rentals with air conditioning in Cook County?
Work out your travel dates and then use the filter tool to view vacation rentals with air conditioning in Cook County on Vrbo. With 1,988 air-conditioned properties available, you can look forward to a cool and comfortable break.
How old do you have to be to rent a vacation rental in Cook County?
The minimum age is usually 16, 18 or 21. It can differ from property to property on Vrbo, so look at the rules of your preferred Cook County vacation home before booking your trip.
How long can I rent a vacation rental in Cook County for?
The length of time you can book a vacation rental in Cook County differs according to the property. Simply enter your desired travel dates to view a list of options offering extended stays. With many amenities like air conditioning and full kitchens, as well as some offering weekly or monthly discounted prices, you’re sure to find somewhere perfect to call your home away from home in Cook County.
Does Vrbo offer discounts for vacation homes in Cook County?
Short break or a much-needed extended escape, Vrbo has some excellent value options in Cook County that’ll match your style and your budget. Browse our weekly and monthly discounts on vacation rentals, or check out what’s just been added with one of our newly listed homes. Whatever you’re after, you’ll find the ideal place to stay — without breaking the bank.

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