Book Holiday Homes in Countryside
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Featured Holiday Homes in Countryside

Great 3 bedroom rental unit near Logan Square

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Cozy Home Sweet Homewood.

Cozy 3-bedroom house in family-oriented Melrose Park.

Updated Forest Park 3 BR Bungalow

Spacious 3-Bedroom Home with Game Lounge & Relaxing Backyard Near Glenbard East

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Charming ModernRetro Home!

Historic home with easy access to Chicago
Countryside 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 Countryside vacation homes are the perfect way for you to wing it.
Holiday houses in Countryside 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 Countryside 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 Countryside adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Countryside 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 Countryside 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.
Countryside Holiday Homes essential information
Accommodation | 723 Holiday Homes |
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Lowest Price | AU$179 |
Highest Price | AU$352 |
Popular accommodation | Great 3 bedroom rental unit near Logan Square, Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24, Cozy Home Sweet Homewood. , Cozy 3-bedroom house in family-oriented Melrose Park., Updated Forest Park 3 BR Bungalow, Spacious 3-Bedroom Home with Game Lounge & Relaxing Backyard Near Glenbard East, Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars, Charming ModernRetro Home!, Historic home with easy access to Chicago |
Holiday Homes in Countryside
Top Locations for Holiday Homes in Countryside
More accommodations in Countryside
Top trending hotels in Countryside

Embassy Suites by Hilton Chicago Downtown River North

Swissotel - Chicago

Crowne Plaza Chicago West Loop by IHG

Hilton Chicago/Magnificent Mile Suites
More ways to explore Countryside
Top picks
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^Subject to availability and chosen travel dates.