Highland Park holiday rentals

We found 392 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 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:

  • 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 Stayz.
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 Stayz?
Stayz 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?
Stayz 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 Stayz, 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 Stayz?
To find Highland Park holiday rentals with free cancellation, just use Stayz'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, Stayz 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 Stayz?
Stayz'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 Stayz 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. Stayz offers something for every taste and budget, from affordable homes in Highland Park to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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 StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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 Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz 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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