Book Holiday Homes in Illinois

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Featured Holiday Homes in Illinois

* On the Wine Trail * Hot Tub * Wi-Fi *

* On the Wine Trail * Hot Tub * Wi-Fi *

Alto Pass
Stay at this vacation home in Alto Pass. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Peachbarn Winery and Von Jakob Winery & ...
* On the Wine Trail * Hot Tub * Wi-Fi *
Notting Hill Cottage

Notting Hill Cottage

Alto Pass
Stay at this vacation home in Alto Pass. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Peachbarn Winery and Von Jakob Winery ...
Notting Hill Cottage
1842 Bavarian Brew House

1842 Bavarian Brew House

Galena
Stay at this vacation home in Galena. Enjoy free WiFi, a garden, and patios. Popular attractions Galena-Jo Daviess County History Museum and West Street Sculpture ...
1842 Bavarian Brew House
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Newly remodeled historic house just steps from the WASHINGTON SQUARE! Sleeps 10!

Newly remodeled historic house just steps from the WASHINGTON SQUARE! Sleeps 10!

Washington
Stay at this vacation home in Washington. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Washington Square and Frankie's Fun Center ...
Newly remodeled historic house just steps from the WASHINGTON SQUARE! Sleeps 10!
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Chicago
Stay at this vacation home in Chicago. Enjoy an in-room coffeemaker. Popular attractions Wrigley Field and Michigan Avenue are located nearby.
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
BIG 5BR/5.5BA all ensuite baths, Hot Tub, Screen Porch.

BIG 5BR/5.5BA all ensuite baths, Hot Tub, Screen Porch.

Galena
Book a stay at this family-friendly vacation home in Galena. Enjoy free WiFi, private pools, and a garden. Our guests praise the helpful staff in our reviews. ...
BIG 5BR/5.5BA all ensuite baths, Hot Tub, Screen Porch.
Stunning / Spacious 6BD Home + garage - Bucktown!

Stunning / Spacious 6BD Home + garage - Bucktown!

Chicago
Stay at this vacation home in Chicago. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Wrigley Field and Michigan Avenue are ...
Stunning / Spacious 6BD Home + garage - Bucktown!
Private 3BR/2BA near golf, historic Galena, lake, owner's club, hiking, skiing

Private 3BR/2BA near golf, historic Galena, lake, owner's club, hiking, skiing

Galena
Book a stay at this family-friendly vacation home in Galena. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Eagle Ridge Resort Golf ...
Private 3BR/2BA near golf, historic Galena, lake, owner's club, hiking, skiing
Furnished Private home in Aurora sleeps 9 guests

Furnished Private home in Aurora sleeps 9 guests

Aurora
Book a stay at this family-friendly vacation home in Aurora. Enjoy free WiFi, a garden, and patios. Popular attractions Aurora Skate Center and Parkside Lanes ...
Furnished Private home in Aurora sleeps 9 guests
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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.

Illinois Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Illinois vacation homes are the perfect way for you to wing it.

Holiday houses in Illinois let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Illinois in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Illinois adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Illinois with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Illinois vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Illinois Holiday Homes essential information

Accommodation
2164 Holiday Homes
Lowest Price
NZ$216
Highest Price
NZ$342
Popular accommodation
* On the Wine Trail * Hot Tub * Wi-Fi *, Notting Hill Cottage, 1842 Bavarian Brew House, Newly remodeled historic house just steps from the WASHINGTON SQUARE! Sleeps 10!, Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!, BIG 5BR/5.5BA all ensuite baths, Hot Tub, Screen Porch. , Stunning / Spacious 6BD Home + garage - Bucktown!, Private 3BR/2BA near golf, historic Galena, lake, owner's club, hiking, skiing, Furnished Private home in Aurora sleeps 9 guests

Top trending hotels in Illinois

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$217 per night from 26 Dec to 27 Dec
NZ$217
includes taxes & fees
26 Dec - 27 Dec
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$216 per night from 7 Jan to 8 Jan
NZ$216
includes taxes & fees
7 Jan - 8 Jan 2025
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
River Hotel
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$342 per night from 10 Jan to 11 Jan
NZ$342
includes taxes & fees
10 Jan - 11 Jan 2025
Book a stay at this eco-certified hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff in our ...
Hyatt Regency Chicago
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Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

3 out of 5
350 West Wolf Point Plaza, Building 2, Chicago, IL
Fully refundable
The price is NZ$230 per night from 7 Jan to 8 Jan
NZ$230
includes taxes & fees
7 Jan - 8 Jan 2025
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
Don't see what you're looking for?
See all available properties in Illinois
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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.

More ways to explore Illinois

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^Subject to availability and chosen travel dates.