12,583 Illinois Holiday Rentals

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Compare Illinois holiday rentals from 17 rental sites including Booking.com, HomeAway, HRS Holidays and more, ranging from $25 to $3729 a night.

Information about Illinois

About Illinois

One of the most celebrated midwestern states, Illinois has everything from small town charm to the windiest of cities. Home to the city of Chicago, Illinois has a claim on one of the greatest cities in America. From a history of gangster activities, the the jazz-age, to raising Abraham Lincoln — Illinois has a rich culture to explore. With walking trails, lake-side vacations and manicured small-towns, the state displays a variety of life.

Things to do in Illinois

Chicago of course is the most popular area of Illinois as the state’s major and unparalleled city. Springfield, the capitol of Illinois, is famous for its ties to Abraham Lincoln who lived there for years. Springfield is like a living Lincoln museum, with historical sites all around.

Best cities to visit in Illinois

Chicago, the windy city on Lake Michigan, is one of the largest cities in the country. Chicago is famed for its gangster history and world-class attractions drawing hoards of visitors. See the Millennium Park, as well as the Lincoln Park Zoo and the Art Institute of Chicago. Aurora and Rockford are smaller cities in Illinois, but also worth checking out.

Best small towns in Illinois

Galena in Illinois is known throughout the Midwest as one of the best small towns to visit. Wirth wineries and breweries, Galena keeps you occupied — you can even rent a hot air balloon! Mount Carroll is another charming small town, with its beautiful streets to walk through and a vibrant art and theater community. Fulton is a town that celebrates its Dutch heritage, and is proud to feature a large windmill, as well as the “Dutch Days” festival.

Best lake vacations in Illinois

Chicago lies on Lake Michigan, meaning that getting to the water isn’t a long haul for locals or visitors. The largest lake in Illinois, Lake Michigan has many nearby rentals for a vacation. With beaches, boats and bike trails, Lake Michigan is at your fingertips. The Chain O’Lakes waterway has 15 lakes that are connected by channels, giving you a wide spread of land to choose from. Carlyle Lake is perfect for sailing, and is the largest lake in the area.

Best National Parks in Illinois

Illinois has many national parks that go through parts of the state. The Trail of Tears, commemorating the Cherokee people goes through Illinois. The Mormon Pioneer historic trail goes through five states, including Illinois. Lastly, the Lewis & Clark historic trail that covers a whopping eleven states can also be found through Illinois.

Vacation Rentals in Illinois

Looking for the perfect vacation rental for your Illinois getaway? Tripping.com’s got your trip covered. Whether you’re seeking a villa, cabin or cottage, Illinois offers 13191 affordable homes to choose from, offering far more amenities, space and convenience than the average hotel room. Select from 2521 properties with high-speed internet, 873 full with jacuzzi and pool, and homes complete with outdoor patio well-suited for a barbecue with loved ones. Whatever your needs, find the perfect rental that best matches your accommodation style and budget.

For travelers planning for an extended stay, long-term lodging and corporate rentals only cost an average of $4369 a month. Save hundreds with Tripping.com and even book instantly with properties marked “Instabook.” Illinois has 13191 gorgeous homes with 1181 pet-friendly rentals to choose from, perfect for your furry friends. Check out our listings now to get the latest deals, and book the right vacation rental for you and the whole family. Feel at home wherever you are and experience an unforgettable vacation with Tripping.com.

Search properties from 17 rental sites in Illinois where the top providers in that area are Booking.com, HomeAway, and HRS Holidays. There are 8992 Booking.com rentals, 1728 HomeAway short term rentals and 1385 HRS Holidays vacation rentals.