Best Vacation Homes in Highland Park
Cottage
10.0(30 Reviews)
2 Bedrooms
1 Bath
6 Guests
Parking
Ocean View
Balcony/Terrace
View
US $393/Night
7 Nights - US $2,749
House
9.3(3 Reviews)
1 Bedroom
1 Bath
2 Guests
204.51 ft²
Private Beach- Parking
- Ocean View
- Balcony/Terrace
US $152/Night
7 Nights - US $1,064
Hotel
9.0(1003 Reviews)
1 Bath
Breakfast- Parking
Pool
Kitchen
US $119/Night
7 Nights - US $831
House
10.0(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
1320 ft²
- Parking
- Kitchen
Air Conditioner
Internet
US $253/Night
7 Nights - US $1,771
Apartment
4 Bedrooms
2 Baths
11 Guests
2066.67 ft²
- Air Conditioner
- Internet
Pet Friendly
Child Friendly
US $542/Night
7 Nights - US $3,794
Apartment
10.0(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $113/Night
7 Nights - US $789
Apartment
9.4(3 Reviews)
2 Bedrooms
1 Bath
7 Guests
743 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $206/Night
7 Nights - US $1,441
Apartment
8.4(16 Reviews)
1 Bedroom
1 Bath
2 Guests
Oceanfront- Parking
- Ocean View
- View
US $174/Night
7 Nights - US $1,217
Highland Park Luxury Rentals
Cottage
10.0(1 Review)
3 Bedrooms
2 Baths
10 Guests
1650 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $670/Night
7 Nights - US $4,689
Apartment
1 Bedroom
1 Bath
11 Guests
2066.67 ft²
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $537/Night
7 Nights - US $3,761
House
9.6(52 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $505/Night
7 Nights - US $3,534
House
10.0(7 Reviews)
3 Bedrooms
4 Baths
7 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $492/Night
7 Nights - US $3,446
New
House
4 Bedrooms
2 Baths
8 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $455/Night
7 Nights - US $3,186
New
House
4 Bedrooms
2 Baths
8 Guests
132 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $453/Night
7 Nights - US $3,168
House
4 Bedrooms
2 Baths
8 Guests
129.17 ft²
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $447/Night
7 Nights - US $3,131
House
4 Bedrooms
2 Baths
9 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $444/Night
7 Nights - US $3,108
Highland Park Pet Friendly Vacation Rentals
Apartment
1 Bedroom
1 Bath
4 Guests
667 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $159/Night
7 Nights - US $1,113
Apartment
2 Bedrooms
1 Bath
7 Guests
753.47 ft²
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $305/Night
7 Nights - US $2,133
Apartment
2 Bedrooms
1 Bath
7 Guests
700 ft²
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $116/Night
7 Nights - US $809
Hotel
8.2(67 Reviews)
5 Baths
621.62 ft²
- Oceanfront
- Breakfast
- Parking
- Pool
US $149/Night
7 Nights - US $1,043
New
Apartment
1 Bedroom
1 Bath
4 Guests
- Air Conditioner
- Pet Friendly
- Child Friendly
Laundry
US $107/Night
7 Nights - US $746
Apartment
8.0(2 Reviews)
4 Bedrooms
2 Baths
11 Guests
2067 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $295/Night
7 Nights - US $2,066
House
4 Bedrooms
2 Baths
8 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $398/Night
7 Nights - US $2,787
Apartment
1 Bedroom
1 Bath
11 Guests
2067 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $307/Night
7 Nights - US $2,150
Highland Park Large Vacation Homes
House
3 Bedrooms
2 Baths
11 Guests
1206 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $280/Night
7 Nights - US $1,961
New
House
3 Bedrooms
2 Baths
11 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $160/Night
7 Nights - US $1,119
Apartment
4 Bedrooms
2 Baths
11 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $149/Night
7 Nights - US $1,043
Apartment
4 Bedrooms
1 Bath
11 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $144/Night
7 Nights - US $1,007
House
10.0(2 Reviews)
6 Bedrooms
4 Baths
12 Guests
Hot Tub- Parking
- Balcony/Terrace
- Kitchen
US $1,230/Night
7 Nights - US $8,612
House
9.0(2 Reviews)
6 Bedrooms
5 Baths
12 Guests
- Hot Tub
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $959/Night
7 Nights - US $6,714
House
8.0(1 Review)
4 Bedrooms
3 Baths
10 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $865/Night
7 Nights - US $6,054
House
6.0(2 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Balcony/Terrace
- Air Conditioner
- Internet
- Pet Friendly
US $999/Night
7 Nights - US $6,993
Why Choose Rent By Owner for your Highland Park Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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
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
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
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
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.
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.
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.
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
Ravinia Pavilion
Highland Park Ambulatory Care Center
Chicago Botanic Garden
Moraine Township
Ravinia 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.
Highland Park Vacation Rental Frequently Asked Questions
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:
- Re-imagined 1880's cottage walking distance to Highwood, Metra, Lake Michigan
- Near Ravinia and Navy Base, charming 3-bedroom house in peaceful Highland Park
- Bright & Modern Home
- Safe & Secure Parkview-Sleep Sanctuary+Kitchen
- .The Pleasant Hill Cottage. North Shore Beaches Ravinia Weddings Families Dining
- Charming Lake Forest Country Estate
- Serene Retreat Awaits You!
- Cozy 2 bed Apt- 2 train stops to the Naval Base!
- Luxury Suite at Private Beach North Shore Residence
- Courtyard by Marriott Chicago Highland Park/Northbrook
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 2026 is over 52 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.
Highland Park Top Rated Vacation Rentals
Hotel
9.0(529 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $202/Night
7 Nights - US $1,416
Hotel
8.4(996 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $113/Night
7 Nights - US $793
Hotel
8.2(146 Reviews)
4 Baths
384.81 ft²
Private Pool- Breakfast
- Parking
- Pool
US $125/Night
7 Nights - US $875
US $128/Night
7 Nights - US $897
