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Highland Park vacation rentals

We found 396 vacation rentals — enter your dates for availability

Discover a selection of 5 homes 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.

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Find out more about Highland Park

Why visit Highland Park

  • Beautiful Beaches: Enjoy the scenic coastline and relax at the family-friendly beaches that Highland Park offers.
  • Urban Parks: Explore the numerous parks that provide outdoor activities and stunning natural beauty.
  • Charming Neighborhoods: Stroll through picturesque streets lined with luxury homes and vibrant local character.
  • Diverse Accommodations: Choose from a variety of vacation rentals, including cozy apartments and spacious homes.
  • Proximity to Exciting Cities: Take a short drive to nearby urban areas for more entertainment and adventure.

Popular types of accommodation in Highland Park

If you're looking for the perfect getaway, Highland Park offers a variety of vacation rentals to suit your needs. Our most popular accommodations include cozy apartments, inviting houses, and stylish condos. Whether you're seeking affordable rentals or spacious house rentals, you'll find the ideal vacation home here. Enjoy transparency, savings, and reassurance while exploring our diverse options in Highland Park.

  • Apartments: The top choice for visitors to Highland Park, offering comfortable living spaces that feel like home.
  • Houses: A favored option for families and groups, providing a cozy and private atmosphere for a relaxing stay.
  • Condos: A popular selection for those seeking modern amenities and shared facilities in a vibrant community.
  • Cottages: These charming retreats provide a quaint and peaceful escape in picturesque settings.
  • Cabins: A unique option for nature enthusiasts, offering a rustic and serene environment to unwind.**

Top attractions near Highland Park

Highland Park, Illinois, offers a delightful family-friendly vacation filled with outdoor activities and urban exploration. Visitors can enjoy beautiful beaches, modern colleges, and urban parks, making it an ideal destination for those seeking a blend of city life and nature. Whether traveling solo or with loved ones, there's something for everyone to explore and enjoy in this charming area.

  • Northwestern University: Located 11 miles from Highland Park, this prestigious university offers a vibrant urban atmosphere. Visitors can explore its stunning campus, featuring modern architecture and beautiful lakefront views, making it a great spot for a leisurely stroll.
  • Six Flags Great America: Situated 15 miles away, this exciting theme park is perfect for families looking for thrills and entertainment. With numerous rides and attractions, it promises a fun-filled day for visitors of all ages.
  • Chicago Botanic Garden: Only 2 miles from Highland Park, this enchanting garden boasts lush landscapes and serene paths. Ideal for romantic walks and family outings, it showcases diverse plant collections and seasonal displays.

Things to do recommended for couples

For a romantic getaway in Highland Park, enjoy a concert at the Ravinia Pavilion, unwind at the luxurious Chevy Chase Country Club, or savor a medieval feast at Schaumburg Medieval Times. Each experience offers a unique atmosphere perfect for couples looking to bond and create lasting memories.

Things to do recommended for families

Your family will love the Northbrook Sports Complex for recreation, Heritage Park for relaxation, and the Great Wolf Lodge Water Park for thrilling water adventures, all within a short drive from Highland Park. Each destination offers unique experiences that cater to family fun and wellness.

Things to do recommended for groups

Experience vibrant shopping at Woodfield Mall, located 15 miles away, perfect for entertainment and family fun. Enjoy a round of golf at the Highland Park Country Club, right in town, and catch a show at the Marriott Theatre, just 6 miles away, for culture and romance.

*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 traveling with a group, family, or pets, or if you're planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful tips for booking on Vrbo.

  • Traveling to Highland Park with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily refine your search to include these options and much more on Vrbo.
  • Traveling to Highland Park with young kids: Traveling with young kids can present some challenges. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private swimming pool. Additionally, thinking about how close you are to family-friendly attractions can enhance your trip.
  • Taking your pets with you to Highland Park: For many families, a vacation wouldn’t be the same without their beloved pet. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and cozy 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 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 in Highland Park

Highland Park, Illinois, offers a delightful blend of family-friendly activities and urban charm. Explore local parks for outdoor fun, and enjoy the scenic beauty of luxury homes that line the streets. Just a short drive away, vibrant cities like Los Angeles and the picturesque landscapes of Southern California await, perfect for those seeking a romantic getaway or a lively atmosphere. Experience the friendly vibe and unique character of this charming destination on your vacation.

  • Chicago: As a sprawling metropolis located about 25 miles south of Highland Park, Chicago is a vibrant city known for its rich culture, diverse neighborhoods, and iconic skyline. Travelers flock to Chicago for family outings, outdoor adventures, and city-themed experiences. Enjoy shopping in the Magnificent Mile, catch a game at one of the famous sports facilities, or explore educational attractions like museums. With landmarks such as Soldier Field and Millennium Park within reach, vibrant arts and entertainment options abound, making it a must-visit destination.
  • Highwood: Just 2 miles from Highland Park, Highwood is a charming city that offers a delightful blend of outdoor scenery and family-friendly activities. Known for its lively atmosphere, Highwood is perfect for those looking to enjoy music concerts and recreational areas. Visit the picturesque lake and beach, or explore the nearby national state park for breathtaking views and nature trails. The community hosts several events throughout the year, creating a warm and inviting environment for visitors.
  • Deerfield: Located 2 miles from Highland Park, Deerfield is a family-oriented city that combines outdoor fun with an urban vibe. Visitors can explore various shopping areas, attend music concerts, and engage with educational venues. Deerfield is home to urban parks and sports facilities, providing ample opportunities for recreation and relaxation. The city's welcoming atmosphere and local attractions make it an excellent choice for a day trip or a leisurely stroll through its scenic neighborhoods.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 a breeze

Are you aiming to save on your upcoming adventure? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that aligns with your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Save more with One Key

When you reserve an eligible Vrbo for your group getaway, you’ll receive OneKeyCash on the full booking amount. Being the organizer truly has its benefits. Become a member of our One Key rewards program to enjoy exclusive savings and earn OneKeyCash on qualifying stays. Sign up today and begin your journey to savings.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for you to plan new trips, manage your travel arrangements, or revisit and organize your existing bookings. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips. To check out the Trip Boards, simply head over to: https://www.vrbo.com/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-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:

  • 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)
  • Orbit Skate Center (12.2 mi / 19.7 km)
  • Palatine Hills Golf Course (13.7 mi / 22 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 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)
  • Waukegan Harbor (12.6 mi / 20.2 km)
  • North Shore Beach Park (14.3 mi / 23 km)
  • Portage Park (15.8 mi / 25.4 km)
  • Foster Avenue Beach (16.1 mi / 25.8 km)
  • Montrose Beach (17 mi / 27.4 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 best area to stay in Highland Park when booking a vacation rental?
When looking for the best area to stay in Highland Park, Illinois, you might want to consider the charming downtown district. This vibrant neighborhood is not only picturesque but also offers a delightful mix of dining, shopping, and entertainment options that can enhance your vacation experience. Here, you can easily access top attractions such as the Ravinia Festival, a renowned outdoor music venue that hosts a variety of performances during the summer months. Additionally, the nearby Rosewood Beach offers beautiful lakefront views and recreational opportunities, making it an ideal spot for relaxation and outdoor activities.

Another great option is the residential area surrounding the Highland Park Historic District. This area boasts beautiful historic homes and tree-lined streets, providing a peaceful retreat while still being close to local amenities. You can explore the stunning architecture and visit the nearby Fort Sheridan Forest Preserve, where nature enthusiasts can enjoy hiking and birdwatching.

In terms of vacation rentals, both the downtown district and the historic area offer a diverse range of properties, from cozy apartments to spacious homes, giving you plenty of choices to find the great fit for your stay.
How much does it cost to rent a vacation home in Highland Park?
Prices for vacation rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Highland Park to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Highland Park vacation house rentals?
You can find great discounts on house rentals in Highland Park on Vrbo, 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.
Where are the best areas for renting a beach house in Highland Park?
For renting a beach house in Highland Park, Illinois, the area along Lake Michigan is the prime location. Specifically, the neighborhoods near Rosewood Beach and Moraine Beach offer beautiful properties with stunning lake views and direct access to sandy shores. Many of these rentals feature amenities such as spacious decks or patios, modern kitchens, and outdoor grilling areas, making them great for families or groups looking to enjoy summer days by the water.

In the vicinity of Rosewood Beach, you can find properties that often include features like private beach access, fire pits for evening gatherings, and ample space for both indoor and outdoor entertaining. These rentals typically provide a comfortable atmosphere, with cozy living rooms and multiple bedrooms, suiting various group sizes.

Moraine Beach, known for its scenic beauty, also provides vacation rental options that allow for easy access to the beach and nearby hiking trails in the surrounding nature preserves. Many homes in this area offer amenities such as large yards, pools, and proximity to local parks, which are ideal for outdoor activities.
What is the most popular type of vacation rental accomodation in Highland Park?
In Highland Park, a variety of vacation rental options are available, with apartments, vacation houses, and cottages all being quite popular. These accommodations are spread throughout the charming neighborhoods of the city, providing easy access to local parks, Lake Michigan, and downtown amenities. Travelers can expect apartments to come equipped with modern kitchens, comfortable living spaces, and often balconies or patios for outdoor enjoyment.

Vacation houses typically offer larger spaces, making them ideal for families or groups. These rentals usually feature multiple bedrooms, private yards, and amenities such as grills and outdoor seating areas, superb for gatherings. Cottages, on the other hand, provide a quaint and cozy atmosphere, often with unique character and proximity to nature trails.
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 a getaway with kids. The neighborhood offers spacious homes with amenities such as fully equipped kitchens, ample living areas for relaxation, and outdoor spaces where children can play safely. Many properties also feature essentials like Wi-Fi and air conditioning to ensure a comfortable stay.

Visitors can enjoy nearby attractions, including beautiful parks and recreational areas, superb for family outings. The proximity to Lake Michigan provides opportunities for beach activities, picnics, and scenic walks.
Can I find long-stay vacation rentals in Highland Park?
A long-stay vacation rental in Highland Park is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Highland Park?
In Highland Park, travelers can find several pet-friendly house rentals that cater to those looking to enjoy the area's beautiful surroundings with their furry companions. Many of these properties come equipped with modern amenities such as spacious living areas, fully stocked kitchens, and private outdoor spaces, great for relaxing after a day of exploration.

Highland Park offers access to numerous parks and green spaces, including the expansive Ravinia Park, known for its scenic landscapes and outdoor music events, making it an ideal spot for walks with pets. The nearby Rosewood Beach also provides a lovely setting for leisurely strolls along the shore, while pet-friendly cafes in the area add convenience for dining out with pets. See all pet-friendly rentals in Highland Park.
Are there any remote work vacation rentals in Highland Park?
In Highland Park, Illinois, there are about 10 vacation rentals that cater to remote work needs. This charming suburban community, located along the shores of Lake Michigan, offers a peaceful environment ideal for productivity. Travelers can expect properties equipped with essential amenities such as high-speed Wi-Fi, dedicated workspaces with desks and comfortable chairs, and sometimes additional features like computer monitors and safes for securing valuables.

The area is also known for its beautiful parks and proximity to the lake, providing opportunities for leisurely breaks and outdoor activities. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Highland Park vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Highland Park with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo 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.
What are popular rental amenities in Highland Park?
In Highland Park, vacation rentals typically feature a variety of amenities that enhance the comfort of guests. Most properties come equipped with kitchens, allowing travelers to prepare their own meals, along with modern appliances like blenders and coffee/tea makers for added convenience. WiFi is commonly available, enabling guests to stay connected during their stay. Many rentals also include kitchen islands, which provide extra space for dining or food preparation.
When is the best time to visit Highland Park for a vacation rental?
The best time to visit Highland Park for a vacation rental is during the vibrant summer months, particularly in July, when the town comes alive with various outdoor activities and events. This peak season, stretching from May to July, offers visitors the superb opportunity to enjoy the warm weather, with temperatures typically ranging from the mid-70s to low 80s Fahrenheit.

During this time, visitors can explore the beautiful beaches along Lake Michigan, take leisurely strolls through the scenic parks, and participate in local festivals that showcase the community's spirit. The lively atmosphere is ideal for families and friends seeking memorable experiences together, whether it's picnicking in the park or enjoying a concert in the town square.

For those looking to travel on a budget, consider visiting in October. This month, while quieter, offers a charming autumn backdrop with the fall foliage providing a stunning display of colors. It's a wonderful time for scenic walks and enjoying the local coffee shops, all while avoiding the peak crowds.

Ultimately, your choice of when to visit Highland Park will depend on your preference for lively summer activities or the tranquil beauty of fall.
How early should I book a Highland Park vacation rental?
Book your Highland Park vacation rental 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 Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Highland Park?
In Highland Park, visitors can enjoy a variety of attractions that highlight the area's natural beauty and cultural offerings. The Ravinia Festival is a major draw, held annually in a picturesque outdoor setting, featuring a wide range of musical performances throughout the summer. Nearby, the Chicago Botanic Garden offers stunning landscapes, walking paths, and themed gardens, making it a great spot for leisurely strolls or picnics.

For those interested in history, the Highland Park Historical Society provides insights into the local heritage, and the charming downtown area features a mix of boutique shops and restaurants. Additionally, the scenic Lake Michigan shoreline offers opportunities for water activities, hiking, and enjoying beautiful sunsets, particularly around the parks like Rosewood Beach and Moraine Park.
Can I change or cancel my Highland Park home rental booking on Vrbo?
To find Highland Park vacation rentals with free cancellation, just use Vrbo'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". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Highland Park vacation rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing 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 favorites, and build the perfect itinerary together.

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