Discover a selection of 500 vacation rentals in Highland Park, IL that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including gardens and backyards and kitchens. Prices start at $100 per night, and condos and houses are popular options for a stay in Highland Park. Either way, you'll find a rental for everyone's needs.
Destination guide

Travel to lively Highland Park

Enjoy the live music and other features of Highland Park. This city's gardens, shopping and sporting events draw many visitors. Six Flags Great America and Wrigley Field are just a couple of the must-sees in the area. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.


Activities and attractions in and around Highland Park

Are you looking for attractions to see in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that Highland Park has to offer. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Six Flags Great America (14.9 mi / 24 km)
  • Sportsman's Country Club (4.1 mi / 6.6 km)
  • Northbrook Sports Complex (4.5 mi / 7.2 km)
  • Willowhill Golf Course (5.1 mi / 8.2 km)
  • Glenview Park Golf Club (6.1 mi / 9.8 km)
  • The Glen Club (6.2 mi / 10 km)
Natural features

Exploring the natural features in Highland Park

Whether you're looking for adventure or just want to appreciate the scenery, Highland Park is a great place to get out in nature. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city center:

  • Lincoln Park (18 mi / 29 km)
  • Rosewood Beach (2.1 mi / 3.4 km)
  • Chicago Botanic Garden (2.2 mi / 3.5 km)
  • Ravinia Park (2.3 mi / 3.7 km)
  • Kent Fuller Air Station Prairie (5.6 mi / 8.9 km)
  • Gallery Park (6.2 mi / 9.9 km)
How to get there

Transportation to and around Highland Park

The nearest airport is in Chicago, IL (PWK-Chicago Executive), located 6.3 mi (10.2 km) from the city center. If you can't find a flight that's convenient for your trip, you can also fly into Chicago, IL (ORD-O'Hare Intl.), which is 14.8 mi (23.9 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 in the city.

How many vacation rentals are available around Highland Park, IL?

Our 2020 property listings offer a large selection of 627 vacation rentals around Highland Park. From 342 condo and apartment rentals to 133 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent a village property in Highland Park?

Quaint buildings lining picturesque streets, friendly locals and a much slower pace of life — villages are truly something special. Are you ready to discover this appealing lifestyle for yourself? Vrbo offers 4 village getaway properties here. Alternatively, you might want to have a look at your other choices. Vrbo has other options that might take your fancy, including 2 town vacation rentals.

Can I rent a hotel in Highland Park?

Switch on the TV and sink into that cushy bed — maybe even order room service if you're feeling indulgent. Nothing beats a good hotel room. Currently, there are 63 options available on Vrbo. Prices start at as little as $50 per night. If that doesn't match your group's style, we've got a range of other rental options to choose from, such as:

  • House: 21 vacation homes. Prices start from $115 per night.
  • Apartment: 19 vacation homes. Prices start from $83 per night.
  • Townhome: 4 vacation homes. Prices start from $64 per night.

Can I stay in Highland Park in a large group?

There's nothing quite as exciting as staying somewhere entirely new with friends and family. The great news is Vrbo has some options to suit big groups. Hotel vacation homes are the most popular option here for large groups of travelers. Our extensive database presently has 15 available. Properties in this area that can house large groups include:

  • On the hunt for vacation homes that can sleep 5 people? We have 36 that will be suitable. The prices start from $99 per night.
  • Looking for a place for 6 people? We have 29 that will suit. You can get one for as little as $114 per night.
  • Trying to find rentals suitable for 8 people? You'll be glad to discover we have 11 that'll be perfect. You can book one for as little as $76 per night.

So don't fear! When you travel with us you can bring your aunt, your cousins and all your pals to Highland Park.

Where are the cheapest rentals in Highland Park?

Vrbo is here to help you reunite with your closest friends and family. Offering a variety of value-packed rentals, you're sure to score a fabulous den that pleases everyone. OHare is a magnet for bargain hunters. And with 3 Vrbo rentals at an average price of $135 a night, it isn't difficult to see why. Ukrainian Village is another place worth considering. Vrbo has 66 rentals here, and the average price is around $211 per night.

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