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Highland Park vacation rentals

We found 310 vacation rentals — enter your dates for availability

Discover a selection of 5 apartments and other vacation rentals in Highland Park that are perfect for your trip. Whether you’re staying in a vacation home with a group or just with your pet, you'll find the amenities you need and want, which might include parking and a hot tub. Whatever you're looking for, you'll find a rental to meet everyone's needs, including accessible or non-smoking choices.
  • Peace of mind
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  • More quality time
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  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
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Find out more about Highland Park

Find out more about Highland Park

Why visit Highland Park

  1. Family-Friendly Attractions: Highland Park offers a variety of activities suitable for all ages, ensuring fun for the whole family.
  2. Beautiful Beaches: Enjoy relaxing days at scenic lakeside parks and pristine beaches ideal for swimming and sunbathing.
  3. Cultural Experiences: Explore local event venues and engage with the vibrant community culture at various festivals and art events.
  4. Charming Neighbourhoods: Discover picturesque neighbourhoods filled with quaint shops, delightful dining options, and friendly locals.
  5. Diverse Accommodation: Choose from a range of vacation rentals, including cozy apartments and spacious homes, for a comfortable stay.

Popular types of accommodation in Highland Park

Explore the diverse vacation rental options in Highland Park, where you can find everything from cozy apartments to spacious houses and modern condos. Whether you're seeking highland park apartments for rent or looking for the perfect rental properties in Highland Park, we’ve got you covered. Discover your ideal accommodation that suits your travel needs and enjoy a memorable stay in this charming neighbourhood.

  • Apartments: A top choice for visitors to Highland Park, offering modern amenities and convenient access to local attractions.
  • Houses: Ideal for families or groups, these homes provide spacious living and a home-like atmosphere.
  • Condos: A popular option, condos offer a blend of comfort and community, often with shared facilities.
  • Cottages: These quaint, charming retreats are perfect for a peaceful getaway amidst nature.
  • Cabins: A favourite among nature enthusiasts, cabins provide a rustic escape with stunning surroundings.**

Top attractions in Highland Park

Highland Park, Illinois, is ideal for family-friendly and outdoor vacations, offering a variety of attractions such as beautiful beaches and modern universities. Visitors can enjoy a vibrant city atmosphere while exploring local event venues and engaging in activities suited for all ages. Whether you're seeking a relaxing day by the water or a cultural experience, Highland Park provides a perfect blend of leisure and excitement for every traveller.

  1. Six Flags Great America: A thrilling theme park featuring exhilarating rides and attractions, perfect for families seeking adventure and entertainment. With a vibrant atmosphere, it's an ideal spot for creating unforgettable memories.
  2. Northwestern University: A prestigious modern university boasting stunning architecture and a vibrant city vibe. It offers a unique experience with its picturesque campus and a rich cultural environment.
  3. Chicago Botanic Garden: A serene botanical garden designed for families, perfect for outdoor exploration and romantic strolls. Its beautiful landscapes provide a tranquil escape just minutes away.

Things to do recommended for couples

For a romantic getaway in Highland Park, enjoy a concert at the Ravinia Pavilion, indulge in luxury at Chevy Chase Country Club, or relish a medieval dining experience at Schaumburg Medieval Times. Each spot offers unique vibes perfect for couples looking to create special memories together.

Things to do recommended for families

Families visiting Highland Park can explore the Northbrook Sports Complex for recreational activities, enjoy the serene atmosphere at Heritage Park, or catch an exciting game at the Welsh-Ryan Arena, all within a short drive from the town.

Things to do recommended for groups

Enjoy a round of golf at Highland Park Country Club, indulge in shopping at Woodfield Mall, or catch a show at the Marriott Theatre for a taste of local culture and entertainment. Each experience promises fun and memorable moments for your group.

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

When planning your travel, whether you're going with a group, family, pets, or seeking extended stays, it's important to prioritize your filters effectively. Here are some helpful Vrbo booking tips for you.

  • Traveling to Highland Park with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Highland Park with young kids: Traveling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close your accommodations are to family-friendly attractions.
  • Taking your pets with you to Highland Park: For many, a family vacation wouldn’t feel complete without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Highland Park: If you're in search of vacation rentals offering discounts 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 monthly accommodations. Don't forget to include amenities like parking, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Highland Park

Highland Park, Illinois, offers a delightful blend of family-friendly attractions and vibrant city life, making it an ideal vacation spot. Explore the charming neighbourhoods and nearby cities, where you can soak in the local culture and enjoy outdoor activities. From the scenic lakeside parks to romantic dining options, Highland Park caters to every traveller’s desires, ensuring a memorable experience filled with friendly people and welcoming atmospheres.

  • Highwood: Highwood is a charming city located a mere 3.2km from Highland Park, making it an easy and enjoyable day trip. Known for its vibrant outdoor scene, visitors can indulge in various family-friendly activities. You can explore local parks, enjoy scenic views, or attend one of the many music concerts that grace the area. Highwood is also home to beautiful landmarks such as the nearby lake and beach, as well as the stunning national state park. Its welcoming atmosphere and recreational areas make it a perfect spot for families seeking a mix of relaxation and adventure.
  • Deerfield: Just 3.2km away from Highland Park, Deerfield is a lively city that combines family-friendly activities with a rich urban experience. It's an excellent destination for those who love to shop, as well as for families wanting to engage in educational outings and music events. Deerfield boasts notable attractions, including a sports facility stadium and vibrant urban parks, which provide ample opportunities for outdoor fun and relaxation. With its blend of cultural experiences and green spaces, Deerfield is a delightful choice for a day of exploration.
  • Bannockburn: Situated 4.8km from Highland Park, Bannockburn is a picturesque neighbourhood that offers a unique blend of family-friendly and outdoor experiences. Visitors can enjoy shopping in local boutiques or catch a performance at the nearby theatre. For sports enthusiasts, there is access to well-maintained golf courses and sports facilities. Bannockburn's charming tourist precinct and inviting atmosphere make it an ideal location for families looking to immerse themselves in a welcoming community while enjoying the best of suburban life.

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. Peak season runs from May to July, while off-peak times, like January and October to November tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January24.6°F (-4.1°C)Light RainMostly CloudySlightly LowSlightly Low
February25.9°F (-3.4°C)Light RainMostly CloudyAverageSlightly Low
March36.1°F (2.3°C)Light RainMostly CloudyAverageSlightly Low
April44.8°F (7.1°C)Light RainMostly SunnyAverageAverage
May55.6°F (13.1°C)Light RainMostly SunnySlightly HighAverage
June66.0°F (18.9°C)Light RainMostly SunnySlightly HighSlightly High
July72.7°F (22.6°C)Light RainMostly SunnySlightly HighSlightly High
August72.3°F (22.4°C)Light RainMostly SunnyAverageSlightly High
September66.2°F (19.0°C)Light RainMostly SunnyAverageAverage
October54.0°F (12.2°C)Light RainMostly SunnySlightly LowAverage
November41.4°F (5.2°C)Light RainMostly SunnySlightly LowAverage
December32.0°F (0.0°C)Light RainMostly CloudyAverageAverage

Booking with Vrbo is simple

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can be a great strategy, as prices tend to vary. Additionally, booking an extended stay often leads to significant savings. To help you find the perfect Vrbo property that fits your budget, feel free to use our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's unique Trip Board offers you a convenient platform to plan new adventures, pick up from where you last stopped, or manage your travel arrangements. You can easily access any properties you've saved or booked, which are neatly categorized under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-ca/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 Six Flags Great America are just a couple of the must-sees in the area. Whether you're planning a family vacation, friends trip or romantic retreat, Vrbo has a great selection of vacation 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 find attractions to see while you're in town? 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 major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • 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 looking for exciting outdoor activities or just want to take in the scenery, Highland Park is a great place to get out in nature. Here are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city center:

  • 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

Fly into Chicago, IL (PWK-Chicago Executive), the closest airport, located 6.8 mi (10.9 km) from the city center. If you're unable to find a flight that fits your schedule, you could also fly into Chicago O'Hare Intl. Airport (ORD), which is 15.1 mi (24.3 km) away.

If you're traveling by train, Highland Park Station, Highland Park Ravinia Station and Highland Park Ravinia Park Station are the main stations in the area.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Highland Park?
According to our data, houses are considered the most popular vacation rental type in Highland Park. But that goes without saying, everyone’s idea of the perfect trip is bound to be different. Vrbo has vacation 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 vacation rental in Highland Park?
A range of things can influence how much you pay for a vacation rental in Highland Park, including the length of stay, type of property and season. Still, all our vacation 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 vacation rental. Type in your Highland Park travel dates to see all your options on Vrbo. 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 rental amenities in Highland Park?
The most popular rental 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, Vrbo vacation 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 vacation 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 vacation rental in Highland Park?
The minimum required age is usually 16, 18 or 21. It can vary from property to property on Vrbo, so check the rules of your chosen Highland Park vacation rental before booking.
How long can I rent a vacation rental in Highland Park for?
The amount of time you can rent a Highland Park vacation rental 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 Vrbo vacation properties may also offer weekly or monthly discounts, so you can stick around for longer for less.

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