Discover Your Perfect Highland Park Vacation Homes

Highland Park Luxury Rentals

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Highland Park Pet Friendly Vacation Rentals

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Why Choose Rent By Owner for your Highland Park Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Highland Park

When should you plan your Vacation Rentals stay?

Timing your visit to Highland Park, Illinois, USA can significantly enhance your experience, as the area offers distinct charms throughout the year—consider planning your stay during the mild spring or warm summer months when the region's natural beauty and local events are at their peak.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During this time, the region experiences warm days and pleasant evenings, making it ideal for exploring the area’s outdoor spaces and cultural activities.

Average Temperature Daytime: 70-80°F - Nighttime: 55-65°F
autumn
Early Fall (September to October)

This period offers comfortable temperatures and vibrant fall foliage, perfect for enjoying local events and scenic views in this destination.

Average Temperature Daytime: 65-75°F - Nighttime: 50-60°F

Off-Season Highlights

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Winter (December to February)

The colder months bring fewer visitors, providing a quiet atmosphere to enjoy the region’s indoor attractions and cozy accommodations.

Average Temperature Daytime: 30-40°F - Nighttime: 15-25°F
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Early Spring (March to April)

Before the full bloom of spring, this off-peak time offers fewer crowds and the chance to experience the area's calm and natural beauty.

Average Temperature Daytime: 45-55°F - Nighttime: 30-40°F

Weekly Weather Forecast for Highland Park

How to Book Your Highland Park Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Highland Park

More Top-Rated Vacation Rentals in Highland Park Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy a private outdoor seating area perfect for relaxing or entertaining in the region’s pleasant weather.
  • Take advantage of a well-maintained garden space that showcases local flora and adds to your outdoor experience.
  • Make use of a spacious patio area ideal for outdoor dining or gatherings during your stay here.
  • Relax by the outdoor fireplace or fire pit, providing warmth and ambiance during cooler evenings in the area.
  • Access a sparkling swimming pool to cool off and unwind while enjoying the scenic surroundings.
  • Utilize outdoor grilling facilities that allow you to enjoy a cookout with views of the natural landscape.
  • Benefit from ample yard space suitable for outdoor activities or for children to play safely in this destination.

Top Attractions Around Highland Park

What attractions are nearby?

Enjoy a variety of outdoor activities and cultural experiences just minutes from your vacation rentals in Highland Park, where scenic parks, local museums, and charming neighborhoods invite you to explore and unwind in this inviting region.

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Family Activities

  • Chicago Botanic Garden: Enjoy a family outing exploring the lush landscapes and seasonal displays at this renowned garden, perfect for learning about native plants and nature conservation.
  • Highland Park Beaches: Spend a relaxing day at the local beaches along Lake Michigan, where you can picnic, play in the sand, and take in stunning lakeside views with your loved ones.
  • North Shore Sculpture Park: Discover outdoor art installations and sculptures that stimulate creativity and offer scenic spots for family photos and leisurely walks.
  • The Highland Park Historical Museum: Engage the whole family with exhibits that showcase the region’s history and culture, providing an educational experience right here in the area.
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Adult Activities

  • Golfing at Highland Park Country Club: Enjoy a round of golf on scenic courses nestled in this charming destination, perfect for relaxing and outdoor recreation.
  • Exploring Ravinia Festival Grounds: Attend world-class outdoor concerts and cultural events in this renowned venue that offers memorable experiences just minutes from your stay.
  • Strolling through the Lakefront Park: Take leisurely walks along the picturesque lakeside parks, where you can unwind and appreciate stunning views of Lake Michigan.
  • Shopping and Dining Downtown: Discover boutique shops and local eateries in the heart of the area, ideal for indulging in regional cuisine and unique finds.

Other Places to Stay in Highland Park, IL

Highland Park Country Club
Highland Park Country Club Vacation Rentals
Moraine Township
Moraine Township Vacation Rentals
Ravinia Pavilion
Ravinia Pavilion Vacation Rentals
Highland Park Ambulatory Care Center
Highland Park Ambulatory Care Center Vacation Rentals
Chicago Botanic Garden
Chicago Botanic Garden Vacation Rentals
Ravinia Park
Ravinia Park Vacation Rentals
More Places to Stay Near Highland Park

Highland Park Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Events and Festivals: Check out the regional calendar to experience community celebrations that showcase the area's vibrant culture during your stay.
  • Plan Outdoor Activities: Take advantage of the region’s scenic parks and waterfronts for outdoor adventures that highlight the natural beauty here.
  • Visit Nearby Dining Options: Discover local eateries and specialty shops to enjoy authentic regional flavors and support the community.
  • Choose a Convenient Location: Select a vacation rental situated close to key attractions and transportation routes to maximize your time exploring the area.

Transportation Options

  • Metra Rail Service: You can easily access reliable train transportation through the Metra, connecting this region to Chicago and other surrounding areas with convenience.
  • Local Bus Transit: The area is served by local bus routes that make getting around within Highland Park and to nearby neighborhoods straightforward and affordable.
  • Car Rental Services: Renting a car offers flexibility for exploring more remote attractions or traveling at your own pace throughout this destination.
  • Taxis and Ride-Sharing: Professional taxi services and ride-sharing options provide convenient, on-demand transportation for quick trips around here or to neighboring towns.

Local Customs Options

  • Community Events and Parades: Participating in local festivals and parades is a cherished tradition here, reflecting a strong sense of community pride.
  • Respect for Nature and Outdoor Activities: The region values outdoor recreation, so you’ll find locals taking pride in preserving parks and engaging in activities like boating and hiking.
  • Historic Preservation: Appreciating the area's history is evident through its well-maintained historic buildings and local museums that celebrate regional heritage.
  • Dining Etiquette and Local Cuisine: When enjoying meals at area restaurants, it’s customary to appreciate locally inspired dishes and engage warmly with staff and neighbors alike.

Frequently Asked Questions About Highland Park?

1. What are the top vacation rentals in Highland Park?

There are a lot of options in Highland Park. If you plan on staying in the Highland Park area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Highland Park:

2. Which vacation homes in Highland Park are best for families?

If you are looking for a family-friendly vacation home in Highland Park, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Highland Park:

3. How many Rentbyowner vacation rentals are available in Highland Park?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 39 in the Highland Park area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Highland Park. 

4. What is the cancellation policy for vacation rentals in Highland Park, Illinois?

Cancellation policies vary depending on the specific property you choose. It's recommended to review the listing details or contact the owner directly to understand the terms applicable to your booking in this area.

5. How do I find pet-friendly vacation rentals in Highland Park, Illinois?

To find pet-friendly options here, utilize the filter options on the listing platform to specify your needs. Details about pet policies are listed within each property description, so be sure to check those before booking.

6. Are there any specific check-in and check-out times I should know about in Highland Park properties?

Check-in and check-out times differ between properties. These details are typically provided on the listing page. If not, contacting the property owner will ensure you have the most accurate information for your stay.

7. Can I get a refund if my plans change after booking a vacation rental here?

Refund eligibility depends on the property's cancellation policy. It’s important to read the specific terms associated with your reservation or speak directly with the owner for clarification.

8. What amenities are usually included in vacation rentals in Highland Park, Illinois?

Amenities vary by property, but common features include Wi-Fi, kitchen facilities, and parking. For detailed information, always review the listing description and reach out to the host if needed.