Skip to navigation
Skip to main content
Skip to footer
Highland Park, IL
Dates
Guests
Favorites
Alerts
Log in
Sign up
Filters
Popular filters
Pets allowed
Accessible
Free Cancellation
Price
$
0
/night
Min price
$
1,000+
/night
Max price
Type of place
Cabin
Cottage
Mansion
House
Hotel
Villa
Boat
Condo
Show more
Rooms & spaces
Bedrooms
Studio
1
2
3
4+
Bathrooms
1
2
3
4
5
6
7
8+
Other spaces
Kitchen
Outdoor space
Workspace
Amenities
Basics
Air conditioning
Laundry
Central heating
Parking
TV
Wifi
Show more
Locations
Lake
Waterfront
Beach
Oceanfront
Ski in/Ski out
Mountains
Accessibility
Only show listings with accessibility features.
Rules & policies
Pets allowed
Smoking allowed
Free cancellation
Price
$
0
/night
Min price
$
1,000+
/night
Max price
Clear
Apply
Type
Cabin
Cottage
Mansion
House
Hotel
Villa
Boat
Condo
Show all
Clear
Apply
More filters
Create Alert
Vacation Rentals in Highland Park, IL
Sort by:
Relevance
Most relevant
Newest first
Price: low to high
Price: high to low
Sort by:
Relevance
Most relevant
Newest first
Price: low to high
Price: high to low
PRICE PER NIGHT
Up to $100
$100 - $199
From $200
ACCOMMODATION TYPES
Apartment
House
Condo
Top-Rated Vacation Rentals in Highland Park, IL
Book a vacation rental in Highland Park that has the highest visitor rating. Here are 6 of the best vacation rentals in Highland Park.
Modern Luxe home w/Gameroom and Electric Fireplace
10
Excellent
·
Details
Highland Park
·
4 br
·
Sleeps 12
·
More
On Site Laundry · Dishwasher · Air Conditioning ·
More
From
$592
/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
On Site Laundry
Dishwasher
Air Conditioning
Swimming Pool
Residents Lounge
Fireplace
Wifi
Furnished
Other spaces
Kitchen
Price drop
Serene Retreat Awaits You!
10
Excellent
·
Details
Highland Park
·
4 br
·
Sleeps 12
·
More
Furnished · Air Conditioning · Kitchen ·
More
From
$425
/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Furnished
Air Conditioning
On Site Laundry
Fitness Center
Oven
Wifi
Dishwasher
Fireplace
Other spaces
Kitchen
Picturesque! Mid Mod Home - 20min from Chicago!
10
Excellent
·
Details
Highland Park
·
3 br
·
Sleeps 8
·
More
Dishwasher · Waterfront · Kitchen ·
More
From
$216
/night
Check availability
Property
House · 3 Beds · 1 bath
Amenities
Dishwasher
Waterfront
Fitness Center
On Site Laundry
Air Conditioning
Wifi
Furnished
Oven
Other spaces
Kitchen, Workspace
Chic Studio - In Downtown Highland Park, by Metra
10
Excellent
·
Details
Highland Park
·
1 br
·
Sleeps 2
·
More
Kitchen · Beach · Lake ·
More
From
$89
/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Beach
Lake
Air Conditioning
Wifi
Waterfront
In Unit Laundry
Furnished
On Site Laundry
Other spaces
Kitchen
Re-imagined 1880's cottage walking distance to Highwood, Metra, Lake Michigan
10
Excellent
·
Details
Highland Park
·
2 br
·
Sleeps 6
·
More
Air Conditioning · Oven · Workspace ·
More
From
$291
/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
Air Conditioning
Oven
Wifi
Furnished
In Unit Laundry
Other spaces
Workspace, Kitchen
Ravinia Festival North Shore Guesthouse
9.3
Excellent
·
Details
Highland Park
·
1 br
·
Sleeps 2
·
More
In Unit Laundry · Free Parking · Air Conditioning ·
More
From
$152
/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
In Unit Laundry
Free Parking
Air Conditioning
Wifi
Assigned Parking
Beach
Furnished
Carpet
Other spaces
Workspace
Expand your search criteria to see more vacation rentals near Highland Park.
Home
>
Illinois Vacation Rentals
>
Highland Park Vacation Rentals
Updated: September 22, 2023
Nearby
Points of Interest
Bus stops
Cafes
Groceries
Nightlife
Parks
Rapid transit stations
Restaurants
Schools
Train stations
Clear
Apply
Search as I move the map