Holiday Rentals in Highland Park, IL

79 available vacation rental offers

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Highland Park, IL holiday rentals
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Best Holiday rentals and Airbnb offers in Highland Park, IL

Best family friendly Highland Park, IL holiday rentals

Among the 79 accommodations in Highland Park, IL, here are the 4 best family friendly rentals

Great For Families Dt Libertyville Near Naval Base - Highland Park, IL
9.8 27 reviews

Great For Families Dt Libertyville Near Naval Base

apartment, Libertyville
This three-bedroom apartment is situated in the centre of Libertyville, just a 13km drive from the Naval Base and within walking distance of the Metra train station, shops and restaurants. The apartment is in a lively area with easy access to local attractions.
The apartment comfortably accommodates up to ten guests with three king-size beds, two twin roll-away beds and a sofa bed. Guests can enjoy keyless entry, fast Wi-Fi, a Roku TV with YouTube TV and Netflix access, a wireless printer and a fully equipped kitchen with a Keurig coffee maker and slow cooker.
The Cozy Retreat 1.7 Miles From The Naval Base - Highland Park, IL
9.6 4 reviews

The Cozy Retreat 1.7 Miles From The Naval Base

apartment, North Chicago
This spacious four-bedroom flat in North Chicago offers convenient access to attractions, being a mere 7-minute drive from Lake Michigan and 4 minutes from Asylum Skate Park.
This family-friendly holiday home accommodates up to 12 guests, featuring a fully equipped kitchen with a fridge, microwave, and dishwasher, complimentary Wi-Fi, air conditioning, and on-site parking.
Dt Libertyville Apt Near Naval Base W/ 50` Tv! - Highland Park, IL
10 3 reviews

Dt Libertyville Apt Near Naval Base W/ 50` Tv!

apartment, Libertyville
This Libertyville apartment is situated 0.3km from MainStreet Libertyville, and within a 4.8km radius of Advocate Condell Child Day Centre, Pine Meadow Golf Club, Lambs Farm, and Independence Grove Beach, with Libertyville Station a short walk away.
This one-bedroom, one-bathroom flat sleeps four guests and offers a fully equipped kitchen, in-unit laundry, and on-site barbecue facilities, alongside proximity to local attractions.
Lovely Studio Near The Beach! (And Heated Floors!) - Highland Park, IL
9.8 205 reviews

Lovely Studio Near The Beach! (And Heated Floors!)

apartment, Highland Park
This studio apartment is situated just a short walk from the centre of Highland Park, Highwood and the beach, offering easy access to shops, restaurants and the beautiful coastline. The accommodation has received excellent ratings for location, cleanliness and overall experience, making it a popular choice for travellers.
The studio is comfortably furnished and can sleep up to three guests. It comes equipped with everything you need for a comfortable stay, including a well-equipped kitchen, a cosy garden and free Wi-Fi.

Best Highland Park, IL holiday rentals with parking

New Your Home Away From Home! - Near Great Lakes Naval Base!! - Highland Park, IL
9.2 53 reviews

New Your Home Away From Home! - Near Great Lakes Naval Base!!

apartment, North Chicago
This lakeside property in North Chicago is located just over 1.6 kilometres from Naval Base Great Lakes and Lake Michigan, offering a peaceful retreat with easy access to both attractions. The accommodation has been consistently rated excellent for its cleanliness, location and user experience.
This four-bedroom house features two bathrooms, a kitchen with a fridge, a garden and parking. You can enjoy free Wi-Fi, a TV and a dining table, as well as outdoor amenities like barbecue grills, making it perfect for families or groups looking for a comfortable and convenient stay.
Chic Mid-century Modern Comfort - Highland Park, IL
10 3 reviews

Chic Mid-century Modern Comfort

apartment, Highland Park
This Highland Park flat is located in the peaceful Sherwood Forest neighbourhood, offering easy access to local attractions (distances to specific landmarks require further information).
The four-bedroom, two-bathroom property sleeps eight guests and boasts a newly renovated mid-century modern design, including air conditioning, parking, and internet access.
The Pleasant Hill Cottage North Shore Enchantment - Highland Park, IL
10 16 reviews

The Pleasant Hill Cottage North Shore Enchantment

apartment, Highwood
This Highwood cottage, a short distance from Lake Michigan beaches, Ravinia Festival, and the Chicago Botanic Garden, offers easy access to Chicago by train.
The three-bedroom, two-bathroom property sleeps ten guests and includes a fully equipped kitchen, garden, fitness centre, parking, and numerous family-friendly amenities such as a travel crib and highchair.
Modern 4bd 2ba Home Near Downtown Metra - Highland Park, IL
No reviews

Modern 4bd 2ba Home Near Downtown Metra

apartment, Highland Park
This contemporary house in Lake County is conveniently located approximately 500 meters from the Metra station, offering easy access to downtown Highwood and Highland Park for dining and shopping, and is a short distance from Cuneo Mansion and Gardens and Grosse Point Lighthouse.
This 12 square meter dwelling boasts four bedrooms and two bathrooms, accommodating up to eight guests with central air conditioning, new flooring, and an open-concept design, while Lake Michigan and Edward L. Ryerson Conservation Area are nearby for outdoor activities.

Frequently asked questions about holiday rentals in Highland Park, IL

  • What are the top family-friendly attractions in Highland Park, IL?

    The Highland Park Zoo is a great option for families, and the Park Avenue Summer Concert Series is a lovely way to spend an evening with the kids. The beaches at Highland Park are also a popular spot for families.
  • What are the best Airbnb and vacation rentals in Highland Park, IL?

    Master Qtr Close To Nature & Easy Urban Facilities, 2-acre Highland Park Retreat With Heated Pool ~ 5* and Guest Room With 1 King Bed are the most popular Airbnb and vacation rentals in Highland Park, IL among travelers.

  • When is the best time to book a vacation rental in Highland Park, IL?

    The best time to book a vacation rental is during the summer months, when the weather is warm and there are many events and festivals happening. If you're looking for a more affordable option, consider booking during the shoulder seasons, spring or autumn.
  • What are the most popular Airbnbs in Highland Park, IL?

  • What events or festivals should visitors check out in and around Highland Park, IL?

    The Ravinia Festival is a must-see, and the Highland Park Arts Center hosts a variety of events throughout the year. The Highland Park Farmers Market is also a popular event, held every Saturday from June to October.
  • What are the best vacation rentals with a pool in Highland Park, IL?

  • What are the best budget-friendly activities in Highland Park, IL?

    A walk along the lakefront is always free, and there are plenty of parks and green spaces to enjoy. You can also check out the free events at the Highland Park Arts Center.
  • What are the best rentals for families and kids in Highland Park, IL?

  • What are the best restaurants with local dishes in Highland Park, IL?

    For a taste of local cuisine, try The Grill on Green Bay, which serves up classic American dishes, or Highland Park's oldest restaurant, The Red Lion Pub, known for its British fare.
  • What are the best rentals or Airbnbs with a jacuzzi in Highland Park, IL?

  • What are the best walking or cycling routes in Highland Park, IL?

    The Lakefront Trail is a popular walking and cycling route, offering stunning views of Lake Michigan. The Highland Park-Fort Sheridan Trail is also a great option, offering a scenic route through the forest.
  • Are there pet-friendly attractions in Highland Park, IL?

    Highland Park is a very dog-friendly city, with many restaurants and businesses welcoming furry friends. The beaches are also dog-friendly during certain hours.
  • What are the benefits of choosing a vacation rental in Highland Park, IL?

    Vacation rentals offer more space and privacy than hotels, and often come with amenities like kitchens and laundry facilities. They are also a great option for families or groups of friends traveling together.

Popular destinations

Best Highland Park, IL holiday rentals with a balcony

Riverfront Libertyville Retreat W/ Outdoor Kitchen - Highland Park, IL
9.0 48 reviews

Riverfront Libertyville Retreat W/ Outdoor Kitchen

apartment, Libertyville
This Libertyville holiday home is situated within 3-5km of Advocate Condell Medical Center, Lambs Farm, and MainStreet Libertyville, offering easy access to local attractions.
The 251 square metre property boasts three bedrooms, three bathrooms, and sleeps eight, including amenities such as a fully equipped kitchen, fitness centre, and in-house laundry facilities.
Lincolnshire Marriott Resort - Highland Park, IL
No reviews

Lincolnshire Marriott Resort

resort, Lincolnshire
The Lincolnshire Marriott Resort is conveniently located just two kilometres from the city centre, putting you within easy reach of the Marriott Theatre, Par-King Skill Golf, and Tribune Tower. This Lincolnshire resort is perfect for exploring the local attractions and enjoying the vibrant atmosphere of the city.
The resort offers a range of facilities to suit all needs, including a spa, fitness centre, swimming pools, tennis courts, and restaurants. Guests can also enjoy the beautiful gardens and relax on the terrace or balcony of their room.
Charming 1-bedroom Apartment With Wifi, Ac In Glenview, Great School District - Highland Park, IL
No reviews

Charming 1-bedroom Apartment With Wifi, Ac In Glenview, Great School District

apartment, Glenview
This Glenview apartment, ideally situated near the Baha'i House of Worship and Grosse Pointe Lighthouse (distances unspecified), offers convenient access to Woodfield Mall and Golf Mill Shopping Centre.
The two-bedroom, one-bathroom flat sleeps four guests and includes Wi-Fi, air conditioning, in-unit laundry facilities, and hairdryers, providing comfortable accommodation in a family-friendly school district.
"Hope Of Evanston" 180°view, 2bdr +2bath Urban Luxury - Highland Park, IL
10 21 reviews

"Hope Of Evanston" 180°view, 2bdr +2bath Urban Luxury

apartment, Evanston
This Evanston apartment is situated 2.1km from Lake Michigan and Northwestern University, a short walk from Davis Metro Station and Evanston Davis Street Station.
This two-bedroom, two-bathroom dwelling sleeps five guests and boasts a private balcony, in-unit fireplace, fully equipped kitchen, and access to a swimming pool and fitness centre; free Wi-Fi is also provided.

Best pet friendly Highland Park, IL holiday rentals

Among the 79 accommodations in Highland Park, IL, here are the 4 best pet friendly rentals

1 King Bed | Non-smoking, Kitchen, Shower - Highland Park, IL
9.6 15 reviews

1 King Bed | Non-smoking, Kitchen, Shower

apartment, Vernon Hills
This Mettawa flat is situated 27 kilometres from Chicago O'Hare International Airport and 20 kilometres from Six Flags Great America, offering proximity to Lake Michigan and Oak Ridge Marsh Nature Park.
This one-bedroom flat, measuring 28 square metres, accommodates two guests and features a separate bedroom, a living area with a sofa bed, air conditioning, heating, free WiFi, and on-site parking, with an on-site picnic area for guests.
Modren 4bd 2ba Home Near Downtown / Metra - Highland Park, IL
No reviews

Modren 4bd 2ba Home Near Downtown / Metra

apartment, Highland Park
This Highland Park flat, located in Lake County, is a short distance from cultural sites such as Ravinia Park and Ravinia Pavilion.
This four-bedroom house accommodates up to eight guests, offering two bathrooms, air conditioning, and is conveniently situated for exploring attractions like the Northbrook Sports Complex and Welsh-Ryan Arena.
Mid-century Modern Turned Modern. Close To All The Attractions That Chicago Has. - Highland Park, IL
No reviews

Mid-century Modern Turned Modern. Close To All The Attractions That Chicago Has.

apartment, Highland Park
This Highland Park holiday home, a four-bedroom, two-bathroom apartment sleeping nine, is situated approximately 3-8 km from Lake Michigan, the Chicago Botanic Garden, and Ravinia Park & Pavilion.
The property boasts essential amenities including Wi-Fi, air conditioning, and is pet-friendly, offering easy access to Kent Fuller Air Station Prairie and convenient proximity to Allstate Arena and Welsh-Ryan Arena.
A Wonderful Getaway Home On The North Shore! - Highland Park, IL
9.8 96 reviews

A Wonderful Getaway Home On The North Shore!

apartment, Highland Park
This Highland Park house, a short distance (0.4 km) from Ravinia Festival and 2.4 km from the Chicago Botanic Garden, offers easy access to the North Shore's cultural attractions and Northwestern University.
The 139 square metre, two-bedroom property sleeps four, boasting a fully equipped kitchen, patio with grill, semi-finished basement with fireplace, Alexa-enabled entertainment system, and parking; pets are welcome.