Highland Park holiday homes

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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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. 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:

  • Chicago Botanic Garden (2.5 mi / 4 km)
  • Heritage Park (7 mi / 11.3 km)
  • North Beach (12.5 mi / 20.2 km)
  • Waukegan Harbor (12.6 mi / 20.2 km)
  • Deer Grove Forest Preserve (13.7 mi / 22.1 km)
  • North Shore Beach Park (14.3 mi / 23 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 best area to stay in Highland Park when booking a holiday rental?
When considering a holiday rental in Highland Park, Illinois, the neighbourhood of Ravinia stands out as a charming option. This picturesque area is well-known for its vibrant arts scene and is home to the renowned Ravinia Festival, which features a variety of concerts and performances throughout the summer. The presence of lush parks and scenic lakefront views adds to its appeal, making it an inviting place to unwind.Another delightful neighbourhood is the Downtown Highland Park area, which boasts a mix of boutique shops, restaurants, and cafes, great for exploring during your stay. The nearby Rosewood Beach is a popular destination, offering beautiful sandy shores and recreational activities, ideal for families and outdoor enthusiasts alike.In terms of accommodation, Highland Park offers a diverse range of properties, from quaint cottages to more spacious family homes, ensuring that visitors can find something that suits their needs.
What is the most popular type of holiday rental accomodation in Highland Park?
In Highland Park, both apartments and holiday houses are equally popular, with around 16 of each type available throughout the area. The apartments are typically located in convenient neighbourhoods, offering a comfortable living space with amenities such as fully equipped kitchens, cosy living areas, and often communal gardens or balconies.On the other hand, the holiday houses tend to provide extra room, making them ideal for families or groups. These properties usually feature multiple bedrooms, private outdoor spaces, and sometimes even amenities like BBQ areas or game rooms.
Are there any family house rentals in Highland Park?
In Highland Park, Illinois, there are several family-friendly house rentals available, making it a great choice for groups travelling together. The area features spacious homes that often come equipped with amenities such as full kitchens, multiple bedrooms, and comfortable living areas, ideal for family gatherings. Many properties also include outdoor spaces where children can play or families can enjoy a barbecue.Visitors will find themselves close to a variety of parks, including the expansive Ravinia Park, which offers outdoor concerts and beautiful walking trails. Additionally, the nearby Lake Michigan shoreline provides opportunities for beach outings and water activities.
Are there pet-friendly house rentals in Highland Park?
In Highland Park, there are several pet-friendly house rentals available, making it a great destination for travellers looking to include their furry companions. Many of these homes come equipped with modern amenities, such as fully stocked kitchens, spacious living areas, and outdoor spaces superb for pets to roam.The neighbourhood offers proximity to a variety of parks where pets are welcome, including the lovely Rosewood Beach and the expansive Heller Nature Centre, which features walking trails and natural areas for pets to explore. Additionally, the local community is known for its pet-friendly cafes and shops, providing an inviting space for both residents and visitors with pets.
Are there any remote work holiday rentals in Highland Park?
In Highland Park, Illinois, there are a variety of remote work-friendly holiday rentals available, with around 32 options to choose from. This charming suburban area offers a peaceful environment conducive to productivity. Many properties come equipped with essential amenities for remote work, including high-speed Wi-Fi, dedicated desk spaces, and comfortable desk chairs, ensuring a professional setting right in the comfort of your holiday rental.Beyond the work aspect, Highland Park boasts beautiful parks and access to Lake Michigan, great for a leisurely break during the day. The local area is rich in cultural attractions, with art galleries, theatres, and a selection of delightful eateries to explore. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Highland Park?
In Highland Park, popular rental amenities typically include well-equipped kitchens, allowing guests to prepare their own meals with ease. Many properties come with a blender and a coffee/tea maker, superb for those who enjoy a morning brew or a smoothie. Dining areas are common, providing a comfortable space for families or groups to gather for meals. Additionally, paper towels are often provided, enhancing the convenience of the stay.
When is the best time to visit Highland Park for a holiday rental?
The best time to visit Highland Park for a holiday rental is during the peak season from May to July, when the area truly comes alive. This vibrant period is characterised by warm weather, with temperatures typically ranging from the low 20s to mid-30s Celsius, making it ideal for outdoor activities such as strolling along the beautiful Lake Michigan shoreline or exploring the local parks and gardens.July stands out as the most popular month, drawing families and visitors eager to enjoy summer festivities, including various community events and concerts in the park. The lively option during this time creates a great environment for travellers seeking a mix of relaxation and adventure.If you're looking for a more budget-friendly option, consider visiting in October. During this month, the crowds thin out, allowing for a more tranquil experience. You can still enjoy the beautiful autumn colours as the leaves change, creating a picturesque backdrop for your exploration.
What are the top attractions in Highland Park?
In Highland Park, visitors can enjoy a variety of attractions that showcase the area's natural beauty and cultural offerings. The Ravinia Festival is a highlight, featuring outdoor concerts and performances in a picturesque setting, making it a must-visit for music enthusiasts. Nearby, the Chicago Botanic Garden offers stunning landscapes and themed gardens, providing ample opportunities for leisurely strolls and picnics.For those interested in history, the Highland Park Historical Society provides insights into the area's past and often hosts engaging events. The local shopping scene is vibrant, particularly along Central Avenue, where visitors can find unique boutiques, cafes, and restaurants. Additionally, the scenic Lake Michigan shoreline offers beautiful parks and beaches, great for outdoor activities such as walking, cycling, and enjoying the views.
Are all fees included in the Highland Park holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Highland Park holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Highland Park with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Highland Park holiday homes?
You can find great discounts on holiday homes in Highland Park on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Highland Park holiday home booking on Bookabach?
To find Highland Park holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Highland Park?
A long-stay holiday home in Highland Park is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Highland Park holiday home?
Book your Highland Park holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Highland Park?
Prices for holiday homes in Highland Park vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Highland Park to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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