6,024 Illinois Holiday Lettings

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Compare Illinois holiday lettings from 13 rental sites including Booking.com, HomeAway, HRS Holidays and more, ranging from $25 to $99999 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

Find the best Illinois vacation rentals with Tripping.com. Choose from 6133 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $25 a night to $99999 a night.

Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? of homes in Illinois offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the rentals with pool or jacuzzi, or relax with the family in one of the homes with cable TV.

For all those dog lovers and cat lovers, Illinois offers pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.

Search properties from 13 rental sites in Illinois where the top providers in that area are Booking.com, HomeAway, and HRS Holidays. There are 2013 Booking.com rentals, 1590 HomeAway short term rentals and 1390 HRS Holidays vacation rentals.