Book Holiday Homes in Hillside

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Featured Holiday Homes in Hillside

Cozy Midway Home

Cozy Midway Home

2 out of 5
Chicago
Located in Chicago, this vacation home is within a 15-minute drive of McCormick Place and Soldier Field.
Cozy Midway Home
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!

Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!

Chicago
With a stay at this vacation home in Chicago (Uptown), you'll be within a 5-minute drive of Wrigley Field and Lake Michigan.
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!
Lincoln Park Living - Suite 2!

Lincoln Park Living - Suite 2!

Chicago
With a stay at this vacation home, you'll be centrally located in Chicago, within a 5-minute drive of Wrigley Field and Lake Michigan.
Lincoln Park Living - Suite 2!
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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 15-minute drive of Wrigley Field and United Center.
Great 3 bedroom rental unit near Logan Square
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

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

Chicago
Located in Chicago (Humboldt Park), this vacation home is within a 10-minute drive of United Center and Michigan Avenue.
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Elegant Mayor's Manor in Central Chicago - 9 Beds + Futons, Close to Downtown!

Elegant Mayor's Manor in Central Chicago - 9 Beds + Futons, Close to Downtown!

Chicago
With a stay at this vacation home in Chicago (Bridgeport), you'll be within a 5-minute drive of McCormick Place and State Street.
Elegant Mayor's Manor in Central Chicago - 9 Beds + Futons, Close to Downtown!
Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design

Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design

Chicago
With a stay at this vacation home, you'll be centrally located in Chicago, a 2-minute drive from United Center and 6 minutes from Chicago Riverwalk.
Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design
Charming 3-bedroom house with AC and WiFi in serene Des Plaines near O’Hare

Charming 3-bedroom house with AC and WiFi in serene Des Plaines near O’Hare

2 out of 5
Des Plaines
The price is AU$499 per night from 20 Nov to 21 Nov
AU$499
includes taxes & fees
20 Nov - 21 Nov
With a stay at this vacation home in Des Plaines, you'll be within a 5-minute drive of Allstate Arena and Donald E. Stephens Convention Center.
Charming 3-bedroom house with AC and WiFi in serene Des Plaines near O’Hare
Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

Chicago
With a stay at this vacation home, you'll be centrally located in Chicago, within a 5-minute drive of Wrigley Field and Lake Michigan.
Chicago Bootlegger House Sleeps 11-22 with 3 parking spots
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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.

Hillside 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 Hillside vacation homes are the perfect way for you to wing it.

Holiday houses in Hillside 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 Hillside 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 Hillside adventures, obvs.

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

Hillside Holiday Homes essential information

Accommodation
592 Holiday Homes
Lowest Price
AU$156
Highest Price
AU$499
Popular accommodation
Cozy Midway Home , Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!, Lincoln Park Living - Suite 2!, Great 3 bedroom rental unit near Logan Square, Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!, Elegant Mayor's Manor in Central Chicago - 9 Beds + Futons, Close to Downtown!, Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design, Charming 3-bedroom house with AC and WiFi in serene Des Plaines near O’Hare , Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

Top trending hotels in Hillside

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$156 per night from 24 Nov to 25 Nov
AU$156
includes taxes & fees
24 Nov - 25 Nov
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
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$181 per night from 17 Dec to 18 Dec
AU$181
includes taxes & fees
17 Dec - 18 Dec
With a stay at River Hotel, you'll be centrally located in Chicago, steps from Michigan Avenue and 5 minutes by foot from Chicago Riverwalk.
River Hotel
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$175 per night from 17 Dec to 18 Dec
AU$175
includes taxes & fees
17 Dec - 18 Dec
With a stay at Club Quarters Hotel, Central Loop, Chicago, you'll be centrally located in Chicago, within a 5-minute walk of State Street and Willis Tower.
Club Quarters Hotel, Central Loop, Chicago
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Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$245 per night from 16 Dec to 17 Dec
AU$245
includes taxes & fees
16 Dec - 17 Dec
With a stay at Eurostars Magnificent Mile, you'll be centrally located in Chicago, steps from State Street and 4 minutes by foot from Michigan Avenue.
Eurostars Magnificent Mile
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See all available properties in Hillside
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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.