Photo by Meghan hernandez

Highland Park holiday homes

We found 323 holiday rentals — enter your dates for availability

Discover a selection of 5 homes 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.

Holiday rentals with weekly discounts - Highland Park

Showing deals for:19 Dec - 26 Dec
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Why visit Highland Park

  • Scenic beaches: Enjoy the beautiful lakeside beaches perfect for swimming, sunbathing, and picnics.
  • Urban parks: Explore the lush parks and nature trails, ideal for walking and family outings.
  • Pinnacle Hill: Hike to the top for stunning views and a chance to unwind among towering pines.
  • Local attractions: Discover the vibrant neighbourhoods, filled with charming shops and eateries.
  • Family-friendly activities: Engage in a variety of fun activities perfect for all ages, ensuring a memorable holiday.

Top attractions near Highland Park

Highland Park, Illinois, is a fantastic spot for family getaways and outdoor adventures. You can explore beautiful beaches, urban parks, and modern universities while enjoying a vibrant city atmosphere. Highlights include Highland Park itself, Humboldt Park, local attractions, and excellent hiking trails in nearby Lincoln Park. Whether you're with family or friends, there's plenty to keep you entertained in this charming locale.

  • Six Flags Great America: A thrilling theme park offering a fantastic array of rides and attractions for the whole family, ensuring a day filled with excitement and adventure, located 24.1km from Highland Park.
  • Loyola University Chicago: A vibrant campus with a modern feel, perfect for exploring its beautiful grounds and enjoying the lively city atmosphere, situated 22.5km away from Highland Park.
  • Northbrook Village Hall: A welcoming civic centre where you can experience friendly local vibes and learn about the community, just 6.4km from Highland Park.

Things to do recommended for couples

For a romantic getaway in Highland Park, enjoy an enchanting concert at Ravinia Pavilion, indulge in luxury at Chevy Chase Country Club, or experience a unique dining adventure at Schaumburg Medieval Times. Each spot offers a special vibe perfect for couples seeking memorable moments together.

Things to do recommended for families

Families can unwind at Camp Pine Woods, only 12.9km from Highland Park, or enjoy activities at the Northbrook Sports Complex, 8.0km away. Heritage Park, located 11.3km from the area, offers lovely green spaces for relaxation and fun family outings.

Things to do recommended for groups

In Highland Park, your group can enjoy a round of golf at Highland Park Country Club, indulge in shopping and entertainment at Woodfield Mall, or experience a captivating show at the Marriott Theatre, perfect for family and friends seeking local culture and fun.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Highland Park

When you're planning a trip—whether with a group, family, or pets, or if you're after longer stays—be sure to refine your search with the right priorities in mind. Here are some helpful Vrbo booking tips just for you.

  • Traveling to Highland Park with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor area for group get-togethers. Thankfully, you can easily filter for all these options—and more—on Vrbo.
  • Traveling to Highland Park with young kids: Journeying with young kids can be quite demanding. It's essential to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, thinking about how close you are to family-friendly activities is a wise move.
  • Taking your pets with you to Highland Park: For many families, a holiday wouldn’t feel complete without their furry companion by their side. If you can relate, take a look at Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels at home.
  • Planning for a long term stay visiting Highland Park: If you're on the hunt for holiday rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on long-term rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Highland Park

Highland Park offers a delightful blend of family-friendly activities and urban charm, making it an ideal spot for your holiday. Explore the scenic Pinnacle Hill, relax among the towering pine trees, and enjoy the vibrant atmosphere of local neighbourhoods. With a range of holiday rentals available, you'll feel right at home while discovering the friendly people and romantic spots nearby. Highland Park promises a memorable experience for all types of travellers.

  • Deerfield: Deerfield is a charming city located 3.2km from Highland Park, offering a delightful blend of family-friendly activities and outdoor experiences. Visitors can enjoy a range of popular venues, from educational institutions to vibrant music concerts. The city boasts a variety of shopping areas, perfect for picking up souvenirs or enjoying a leisurely day out. Key attractions include a local sports facility stadium and beautifully maintained urban parks, making it an ideal spot for both relaxation and recreation.
  • North Suburbs: Just 4.8km from Highland Park, the North Suburbs area is a wonderful destination for families and business travellers alike. This bustling region features shopping centres and malls, providing ample opportunities for retail therapy. With a focus on outdoor experiences, visitors can explore various parks and recreational areas. Local landmarks include a sports facility stadium and a lively tourist precinct, ensuring there’s always something happening. The North Suburbs offer a perfect mix of leisure and convenience for all types of travellers.
  • Northbrook: Located 6.4km from Highland Park, Northbrook presents a vibrant city atmosphere with a strong emphasis on family activities and outdoor fun. The area is known for its engaging music concerts and educational opportunities, making it a great spot for families. Northbrook's shopping areas offer a diverse range of options for visitors looking to indulge in a bit of retail therapy. Key attractions include a local sports facility stadium and expansive urban parks, providing plenty of opportunities for relaxation and outdoor adventures.

Best time to go to Highland Park

If you're planning a trip to Highland Park, it's a good idea to check both the weather and property rates. The warmest month is July.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January24.6°F (-4.1°C)Light RainMostly CloudySlightly Low
February25.9°F (-3.4°C)Light RainMostly CloudyAverage
March36.1°F (2.3°C)Light RainMostly CloudyAverage
April44.8°F (7.1°C)Light RainMostly SunnyAverage
May55.6°F (13.1°C)Light RainMostly SunnySlightly High
June66.0°F (18.9°C)Light RainMostly SunnySlightly High
July72.7°F (22.6°C)Light RainMostly SunnySlightly High
August72.3°F (22.4°C)Light RainMostly SunnyAverage
September66.2°F (19.0°C)Light RainMostly SunnyAverage
October54.0°F (12.2°C)Light RainMostly SunnySlightly Low
November41.4°F (5.2°C)Light RainMostly SunnySlightly Low
December32.0°F (0.0°C)Light RainMostly CloudyAverage

Booking with Vrbo is a breeze

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Also, extending your stay can often lead to substantial savings. To discover the ideal Vrbo accommodation that fits your budget, make use of our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's handy Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, or manage your travel arrangements. You can easily find properties you've saved or booked in the Potential, Upcoming, or Current Trips sections. To start using Trip Boards, simply visit: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

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 Wrigley Field 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)
  • Conway Farms Golf Club (5.9 mi / 9.4 km)
  • Chevy Chase Country Club (6.3 mi / 10.1 km)
  • The Glen Club (6.5 mi / 10.4 km)
  • The Dome at the Parkway Bank Sports Complex (14.4 mi / 23.1 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)
  • Lake Park (12.7 mi / 20.4 km)
  • Loyola Beach (14.1 mi / 22.7 km)
  • North Shore Beach Park (14.3 mi / 23 km)
  • Kathy Osterman Beach (15.5 mi / 24.9 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. Bookabach 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 Bookabach. 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, Bookabach 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 Bookabach, 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 Bookabach holiday properties may also offer weekly or monthly discounts, so you can stick around for longer for less.

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