Highland Park Rentals
From $149 per night (USD)VRBO
Cute Ranch House close to town monthly stay
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Newly remodeled and beautifully furnished ranch house with 3 bed and 2 bath (1 bathroom is in basement) can sleep 6. Hug ...
From $149 per night (USD)VRBO
From $513 per night (USD)Expedia
Serene Retreat Awaits You!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Set in the midst of an affluent neighborhood, this spacious and sunny four bedroom retreat offers all the comforts of a ...
From $513 per night (USD)Expedia
From $324 per night (USD)VRBO
Re-imagined 1880's cottage walking distance to Highwood, Metra, Lake Michigan
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Escape the city and relax in our newly renovated historic cottage and gardens. Peaceful yet centrally located, vintage y ...
From $324 per night (USD)VRBO
From $164 per night (USD)Expedia
Chic Studio - In Downtown Highland Park, by Metra
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to our beautiful and elegant studio apartment located in the heart of downtown Highland Park. Our space is perfe ...
From $164 per night (USD)Expedia
From $110 per night (USD)VRBO
Safe and Secure, Charming, Clean Studio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our studio apartment is in a secure building, centrally-located in the walkable Rivinia Business District of Highland Pa ...
From $110 per night (USD)VRBO
From $128 per night (USD)VRBO
Clean, Quiet, Secure, with Beautiful Park Views - 1 bedroom plus den in Rivinia
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Our 1 bedroom + den apartment is peaceful & stylish for your monthly living needs. Centrally-located 2 blocks from UP-N ...
From $128 per night (USD)VRBO
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Hidden Gem Cottage alongside Park, by Beach, Train, Ravinia, Botanic Garden
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Unique Hidden Gem Cottage, alongside beautiful green park, famous Green Bay Trail, Ravinia and Botanic Gardens, Few bloc ...
Click For PricingVRBO
From $115 per night (USD)Expedia
Safe & Secure Parkview-Sleep Sanctuary+Kitchen
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Perfect location, close to everything and quiet. Charming apartment with designer touches overlooking a park and just a ...
From $115 per night (USD)Expedia
From $170 per night (USD)VRBO
Chic Studio in Downtown Highland Park near Metra
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to downtown Highland Park! Experience comfort and convenience in our cozy studio apartment with FREE parking. Ju ...
From $170 per night (USD)VRBO
From $180 per night (USD)Expedia
Stunning & Stylish Downtown Studio - Highland Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Experience the charm of downtown Highland Park, IL, in our newly-remodeled, stylish studio apartment steps from the Metr ...
From $180 per night (USD)Expedia
From $550 per night (USD)VRBO
Entire home, close to Ravinia Festival, Lake, Town, and Train to the city.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Your Highland Park R&R plus adventures begin & launch from this vintage, historical, 3-bedroom eco-cottage. Built origin ...
From $550 per night (USD)VRBO
From $648 per night (USD)Expedia
Near Ravinia and Navy Base, charming 3-bedroom house in peaceful Highland Park
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 7
Modern 3-bed, 4-bath home in Highland Park, IL, steps from Ravinia Festival. Recently renovated with an open-concept liv ...
From $648 per night (USD)Expedia
From $1141 per night (USD)VRBO
Sunset Manor: Opulent Mansion, Ultimate Serenity Awaits
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Welcome to Sunset Manor, a luxurious 6-bedroom, 4.5-bathroom residence where elegance and comfort come together to creat ...
From $1141 per night (USD)VRBO
From $984 per night (USD)Expedia
Highland Park Family Ranch - Walk to Lake & Metra to Chicago!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Your Highland Park Retreat Awaits! Nestled in the peaceful and walkable Chicago's North Shore neighborhood of Highland ...
From $984 per night (USD)Expedia
From $195 per night (USD)VRBO
Charming 2-bedroom apartment in delightful Highwood 2 minutes to Train station!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
You will be close to everything when you stay at this centrally located 2nd floor apartment. Walking distance to Highwoo ...
From $195 per night (USD)VRBO
From $202 per night (USD)Expedia
Cozy 2 bed Apt- 2 train stops to the Naval Base!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Your family will be close to everything when you stay at this centrally located apartment in downtown Highwood. Walking ...
From $202 per night (USD)Expedia
From $756 per night (USD)VRBO
Stunning 4-bedroom house combines comfort, elegance, and is pet-friendly
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 7
Welcome to your home away from home! This charming 4-bedroom retreat sleeps up to 7 guests and features 2 queen beds an ...
From $756 per night (USD)VRBO
From $841 per night (USD)Expedia
The Pleasant Hill Cottage-Storybook Luxury Near Lake Michigan & Heart Of It All!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Greetings from The Pleasant Hill Cottage Keepers! Built in the 1930s, she carries nearly a century of stories within he ...
From $841 per night (USD)Expedia
From $426 per night (USD)VRBO
Mid-century modern turned MODERN. Close to all the attractions that Chicago has.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Located in Highland Park, this house is a dream. With 4 bedrooms including 2 queen beds and 2 full beds, guests will hav ...
From $426 per night (USD)VRBO