Highland Park, Chicago holiday accommodation: short-term house rentals & properties

Discover a selection of 5 apartments and other holiday rentals in Highland Park that are perfect for your trip. Whether you’re staying in a holiday home with a group or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include air conditioning and a pool. At the end of the day, you'll find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

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Find the best place to stay - Highland Park

The Sunset Manor - Luxe Mansion for Serene retreat

Sleeps 12 · 6 bedrooms · 4+ bathrooms

Welcome to our Storybook Cottage 🏡, gushing w/ cozy-warm-spacious glitz+comfort💞

Beautiful+Serene+Upscale EcoGem by ALL the Action~>Beach+Lake+Ravinia+Train+Town

Sleeps 8 · 3 bedrooms · 1 bathroom

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

The natural setting of Highland Park is ready to explore

Enjoy the live music and other features of Highland Park. This city's gardens, shopping and sporting events draw many visitors. Naval Base Great Lakes and Six Flags Great America are just a couple of the must-see attractions in the area. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Sightseeing in and around Highland Park

Are you hoping to discover attractions to visit in the city? Venture out of your cosy holiday rental and experience everything that Highland Park has to offer. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

Six Flags Great America (14.5 mi / 23.4 km)
Northbrook Sports Complex (4.8 mi / 7.8 km)
Chevy Chase Country Club (6.3 mi / 10.1 km)
The Glen Club (6.5 mi / 10.4 km)
Adagio Teas (8.6 mi / 13.9 km)
Kemper Lakes Golf Club (10.1 mi / 16.3 km)

Exploring the natural features in Highland Park

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, Highland Park is a great spot to appreciate mother nature. These are some of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

Chicago Botanic Garden (2.5 mi / 4 km)
Heritage Park (7 mi / 11.3 km)
North Shore Beach Park (14.3 mi / 23 km)
Kathy Osterman Beach (15.5 mi / 24.9 km)
Portage Park (15.8 mi / 25.4 km)
Foster Avenue Beach (16.1 mi / 25.8 km)

How to get to and around Highland Park

Book a flight to Chicago, IL (PWK-Chicago Executive), the closest airport, located 6.8 mi (10.9 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Chicago O'Hare International Airport (ORD), which is 15.1 mi (24.3 km) away.

If you prefer to travel by train, Highland Park Station, Highland Park Ravinia Station and Highland Park Ravinia Park Station are the main stations that serve the city.

Frequently asked questions

What is the most popular type of holiday home accommodation in Highland Park?

According to our data, houses are considered the most popular holiday home type in Highland Park. But that goes without saying, everyone’s idea of the perfect trip is bound to be different. Stayz has holiday homes of all sizes, shapes and budgets, so you’re bound to find the best fit for your needs.

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

A range of things can influence how much you pay for a holiday home in Highland Park, including the length of stay, type of property and season. Still, all our holiday homes have one thing in common — amazing value. Simply add your travel dates to find your ideal escape.

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

When you travel and the size and style of the property will determine the cost of your beachside holiday home. Type in your Highland Park travel dates to see all your options on Stayz. Looking for basics like WiFi, or perks like a private pool? Use our filters to pick the amenities and features you need.

What are popular home amenities in Highland Park?

The most popular home amenities people look for in Highland Park include a fireplace, a garden and a barbecue grill. Whether you’re on the road with pals, family or even pets, Stayz holiday homes include the best amenities for fun and relaxation with the people you cherish the most.

What are the top attractions for families in Highland Park?

Keeping the kiddos entertained during your Highland Park holiday is child’s play with these top family-friendly attractions:

Kohl Childrens Museum
Wagner Farm
Grove National Historic Landmark

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

The minimum required age is usually 16, 18 or 21. It can vary from property to property on Stayz, so check the rules of your chosen Highland Park holiday home before booking.

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

The amount of time you can rent a Highland Park holiday home for is up to each property. Simply put in your travel dates to browse available options offering extended stays. They come with all you need to make your extended trip more convenient and comfortable, such as kitchens and yards. Some Stayz holiday properties may also offer weekly or monthly discounts, so you can stick around for longer for less.