Highland Park holiday rentals

We found 391 holiday rentals — enter your dates for availability
Discover a selection of 8 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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  • All the privacy of home

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Why visit Highland Park

  • Scenic Urban Parks: Enjoy the beauty of Highland Park’s green spaces and lakeside retreats, perfect for leisurely strolls and picnics.
  • Cultural Attractions: Experience local history and community events in a town that celebrates its heritage and artistic endeavours.
  • Vibrant Downtown: Wander the picturesque streets, taking in the charming ambience and lively local scene.
  • Family-Friendly Atmosphere: A welcoming community offering relaxation and recreation for visitors of all ages.
  • Diverse Local Experiences: Embrace scenic landscapes, urban parks and cultural spots, ensuring a memorable holiday escape.

Popular types of accommodation in Highland Park

Discover Highland Park, Illinois, a charming city offering a mix of cultural attractions and scenic parks. Choose from cosy apartments, private holiday homes and stylish condos, ensuring free parking and the best Highland Park accommodation options. Embrace the local history with prominent landmarks and vibrant community events for an unforgettable stay in this delightful town.

  • Apartments: The most sought-after option, offering modern comforts and convenient amenities for a relaxing stay.
  • Private Holiday Homes: A popular choice for families and groups, providing spacious living areas and a home-like atmosphere.
  • Condos: These stylish units typically feature shared facilities, perfect for those seeking a blend of comfort and community.
  • Cottages: Ideal for a charming and quaint getaway, these cosy retreats offer a peaceful retreat from the hustle and bustle.
  • Cabins: A favourite among nature enthusiasts, cabins provide a rustic escape with direct access to the great outdoors.**

Top attractions near Highland Park

Highland Park, Illinois beckons families and outdoor enthusiasts with its charming urban parks, picturesque reserves, and inviting beaches. Enjoy a blend of leisure and culture as you explore its scenic landscapes and vibrant local attractions. Whether you seek relaxation or adventure, this destination offers a delightful retreat for a memorable holiday experience.

  • Six Flags Great America: A thrilling theme park offering exhilarating rides and attractions for all ages, perfect for family fun and creating lasting memories.
  • Chicago Botanic Garden: A stunning botanical garden that features beautifully landscaped grounds, serene walking paths, and diverse plant collections, ideal for family outings or romantic strolls.
  • Rosewood Beach: A picturesque beach with soft sand and refreshing waters, providing a tranquil setting for sunbathing, picnicking, and enjoying the scenic lake views.

Things to do recommended for couples

Searching for a romantic getaway in Highland Park? Enjoy a leisurely stroll along the stunning Lake Michigan shoreline or indulge in a wine tasting at a local vineyard. Don't forget to explore the charming boutiques and enjoy a candlelit dinner at a quaint restaurant for a memorable evening.

Things to do recommended for families

Your family will delight in the beautiful beaches of Lake Michigan at Rosewood Beach, explore the interactive exhibits at the Highland Park Historical Society, and enjoy a day at Ravinia Park, where you can picnic and listen to live music in a picturesque setting.

Things to do recommended for groups

Discover Highland Park's rich heritage, explore local art galleries, and enjoy scenic walks along the lakefront. Relish group dining at cosy bistros and savour live music at quaint pubs. Experience authentic local culture and create unforgettable memories with your group.

*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

If you're travelling with a group, as a family, bringing your pets along, or seeking longer stays, be sure to refine your search according to your key priorities. Here are some helpful booking tips from Stayz for you.

  • Traveling to Highland Park with a group: Consider how many bedrooms you'll require, along with features like a fully-equipped kitchen or an outdoor area for a group get-together. Thankfully, you can refine your search for all these options, and many more, on Stayz.
  • Traveling to Highland Park with young kids: Travelling with young children can present its own set of challenges. It’s essential to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about your closeness to attractions that are family-friendly.
  • Taking your pets with you to Highland Park: For many, a family holiday simply wouldn’t be complete without their four-legged companion. If this resonates with you, consider exploring Stayz properties that welcome pets. Most of these properties offer feeding bowls and beds, ensuring that every member of the family feels comfortably at home.
  • Planning for a long term stay visiting Highland Park: If you're searching for holiday rentals with offers for stays of a month or more, you've come to the perfect place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features such as a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Highland Park

Highland Park offers a delightful urban retreat, blending family-friendly charm with a vibrant business atmosphere. Wander the picturesque downtown, enjoy leisurely strolls along scenic streets, and savour the local ambience. The city’s parks and cultural spots provide a perfect setting for both relaxation and entertainment, ensuring a memorable holiday experience in this welcoming community.

  • Chicago: As a bustling metropolis, Chicago is a must-visit for those seeking a vibrant urban experience. Just a short journey from Highland Park, the city boasts an impressive array of attractions, including renowned shopping districts, lively entertainment venues, and captivating theatres. Explore iconic landmarks like Millennium Park and the Art Institute, or catch a game at one of the city's famous sports facilities. With its diverse neighbourhoods and outdoor spaces, Chicago offers a rich tapestry of experiences that cater to families and city lovers alike.
  • Deerfield: Located a mere 3km from Highland Park, Deerfield is a charming city that provides a delightful mix of family-friendly activities and urban conveniences. Visitors can enjoy a leisurely day at the local shopping centre or explore educational venues that cater to all ages. The city is also home to scenic urban parks where you can unwind and enjoy the outdoors. With its welcoming atmosphere and easy access to nearby attractions, Deerfield is an ideal spot for those looking to experience a suburban escape.
  • North Suburbs: Just 5km away, the North Suburbs offer a picturesque blend of family-oriented activities and recreational opportunities. Here, you can indulge in shopping at various centres or catch a show at a local theatre. The area is dotted with inviting parks and sports facilities, perfect for outdoor enthusiasts. With its close-knit community feel and access to beautiful lakes, the North Suburbs provide a serene retreat while remaining conveniently close to the excitement of Highland Park.

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 Stayz is simple

Looking to trim costs on your upcoming escape? Consider keeping your travel dates flexible, as prices can fluctuate. Moreover, booking a longer stay can often result in significant savings. To help you find the ideal Stayz property that suits your budget, simply use our filters to search by price, location, and type of holiday rental.

Stayz Trips: Effortless planning

Stayz’s innovative Trip Board provides you with a dedicated space to craft fresh itineraries, pick up from where you paused, or review and arrange your plans. Properties that you have previously saved or booked are now categorised under Potential, Upcoming, or Current Trips. To access Trip Boards, simply visit: https://www.stayz.com.au/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. Six Flags Great America 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)
  • Chevy Chase Country Club (6.3 mi / 10.1 km)
  • The Glen Club (6.5 mi / 10.4 km)
  • Kemper Lakes Golf Club (10.1 mi / 16.3 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:

  • Rosewood Beach (1.8 mi / 3 km)
  • Chicago Botanic Garden (2.5 mi / 4 km)
  • Heritage Park (7 mi / 11.3 km)
  • Wilmette Park District Swimming Beach (9 mi / 14.6 km)
  • Dawes Park (11.5 mi / 18.5 km)
  • North Beach (12.5 mi / 20.2 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.