Book Holiday Homes in Countryside

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Featured Holiday Homes in Countryside

Great 3 bedroom rental unit near Logan Square

Great 3 bedroom rental unit near Logan Square

Chicago
With a stay at this vacation home, you'll be centrally located in Chicago, within a 10-minute drive of Wrigley Field and Lincoln Park Zoo.
Great 3 bedroom rental unit near Logan Square
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

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

Chicago
With a stay at this vacation home, you'll be centrally located in Chicago, within a 5-minute drive of Wrigley Field and Lincoln Park Zoo.
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Cozy Home Sweet Homewood.

Cozy Home Sweet Homewood.

Homewood
With a stay at this vacation home in Homewood, you'll be within a 5-minute drive of Ravisloe Country Club and Oak Hill Park.
Cozy Home Sweet Homewood.
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Cozy 3-bedroom house in family-oriented Melrose Park.

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

Melrose Park
Located in Franklin Park, this vacation home is within a 15-minute drive of Donald E. Stephens Convention Center and Allstate Arena.
Cozy 3-bedroom house in family-oriented Melrose Park.
Updated Forest Park 3 BR Bungalow

Updated Forest Park 3 BR Bungalow

Forest Park
With a stay at this vacation home in Forest Park, you'll be within a 15-minute drive of United Center and Art Institute of Chicago.
Updated Forest Park 3 BR Bungalow
Spacious 3-Bedroom Home with Game Lounge & Relaxing Backyard Near Glenbard East

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

Lombard
Located in Lombard, this vacation home is within a 5-minute drive of Lilacia Park and Yorktown Shopping Center.
Spacious 3-Bedroom Home with Game Lounge & Relaxing Backyard Near Glenbard East
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

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

Chicago
With a stay at this vacation home in Chicago (Near North Side), you'll be within a 5-minute drive of Michigan Avenue and Lake Michigan.
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Charming ModernRetro Home!

Charming ModernRetro Home!

Elmhurst
With a stay at this vacation home in Elmhurst, you'll be within a 15-minute drive of Donald E. Stephens Convention Center and Allstate Arena.
Charming ModernRetro Home!
Historic home with easy access to Chicago

Historic home with easy access to Chicago

Glen Ellyn
A stay at this vacation home places you in the heart of Glen Ellyn, within a 5-minute drive of Wheaton College and Billy Graham Center Museum.
Historic home with easy access to Chicago
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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.

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
Lowest Price
AU$263
Highest Price
AU$367
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

Top trending hotels in Countryside

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$274 per night from 30 Apr to 1 May
AU$274
includes taxes & fees
30 Apr - 1 May
With a stay at Embassy Suites by Hilton Chicago Downtown River North, you'll be centrally located in Chicago, just a 4-minute walk from Michigan Avenue and 9 ...
Embassy Suites by Hilton Chicago Downtown River North
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 AU$263 per night from 1 May to 2 May
AU$263
includes taxes & fees
1 May - 2 May
With a stay at Congress Plaza Hotel, you'll be centrally located in Chicago, steps from Columbia College Chicago and Museum of Contemporary Photography.
Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$295 per night from 11 May to 12 May
AU$295
includes taxes & fees
11 May - 12 May
With a stay at Hilton Chicago/Magnificent Mile Suites, you'll be centrally located in Chicago, steps from Michigan Avenue and 8 minutes by foot from Lake ...
Hilton Chicago/Magnificent Mile Suites
Save an average of 15% on thousands of hotels when you're signed in
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
323 E Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$367 per night from 2 May to 3 May
AU$367
includes taxes & fees
2 May - 3 May
A stay at Swissotel - Chicago places you in the heart of Chicago, within a 10-minute walk of Michigan Avenue and Millennium Park.
Swissotel - Chicago
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See all available properties in Countryside
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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.

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^Subject to availability and chosen travel dates.