Highland Hills, Chicago holiday homes: holiday houses & more

Discover a selection of 24 homes and other holiday rentals in Highland Hills that are perfect for your trip. Holiday rentals offer the amenities that you expect for you and your friends, family or even pets, such as parking and a washer and dryer. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Find the best place to stay - Highland Hills

Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking

Sleeps 5 · 2 bedrooms · 2 bathrooms

Cozy One Bedroom, Washer Dryer, Central Location, Fireplace, Monthly Discounts

Sleeps 4 · 1 bedroom · 1 bathroom

Find spaces that suit your style

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Transport to and around Highland Hills

Fly into Chicago O'Hare International Airport (ORD), the closest airport, located 9.9 mi (16 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Chicago Midway Airport (MDW), which is 14.2 mi (22.8 km) away.

Frequently asked questions

How much does it cost to rent a holiday home in Highland Hills?

Length of stay, property type and season are among the factors that can affect the price of a holiday home. Simply click on your dates of travel to find your perfect match. From quaint country cottages to expansive villas, all Bookabach holiday homes offer unbeatable value.

How much does it cost to rent a beach house in Highland Hills?

The average price for a holiday home by the beach in Highland Hills will depend on when you're going and the size and style of property you're looking for. Find prices quickly and easily on Bookabach by entering your destination and travel dates. Then use our filter tool to select the number of bedrooms and amenities essential to you, like a pool, air conditioning and WiFi.

What are the top attractions for families in Highland Hills?

Give the kiddos a day out at these exciting family-friendly attractions in Highland Hills:

Yorktown Shopping Centre
Lilacia Park

How old do you have to be to rent a holiday home in Highland Hills?

The minimum age allowed can differ between properties on Bookabach, so be sure to check the rules of the holiday home in Highland Hills you're interested in. But usually, it's 16, 18 or 21.

How long can I rent a holiday home in Highland Hills for?

How long you can book a holiday home in Highland Hills varies according to the property. Simply enter your desired travel dates to display a list of options offering extended stays. With loads of creature comforts like washing machines and kitchens, as well as some offering weekly or monthly discounts, you're sure to get a perfect place to call your home away from home in Highland Hills.