Best Holiday rentals and Airbnb offers in Highland Park, IL
8.8 39 reviews
Highland Park, IL
15/08 – 15/09
SG$198/nighttotal: SG$6138 (31 )
Comfortable 2 Bedroom House Near Great Lakes Navy Base Ideal For Families
2 2
apartment , North Chicago
This North Chicago flat offers convenient access to Great Lakes Naval Station, Rosalind Franklin University, Six Flags Great America (approximately 3 kilometres away), American Place Casino, and Independence Grove Nature Preserve. This two-bedroom residence accommodates up to six guests and features a full kitchen, a 55-inch TV with Roku, and private access to the entire house, with amenities including air conditioning, Wi-Fi, and a garden with a barbecue.
Highland Park, IL
11/07 – 14/07
SG$812/nighttotal: SG$2436 (3 )
Modern 4bd 2ba Home Near Downtown Metra
4 2
house , Highland Park
This four-bedroom detached house in Highland Park is located 16 kilometres from Six Flags Great America and 18 kilometres from O'Hare International Airport, with a Metra station nearby for convenient access to downtown Chicago. This modern dwelling offers 12 square metres of floor area, accommodates up to 12 guests, and features four bedrooms, two bathrooms, air conditioning, and complimentary WiFi, with Openlands Lakeshore Beach situated 1.9 kilometres away.
9.8 18 reviews
Highland Park, IL
15/08 – 15/09
SG$385/nighttotal: SG$11935 (31 )
Home W/ Porch In Dt Libertyville Near Naval Base
3 2
apartment , Libertyville
This Libertyville house, less than 2km from MainStreet Libertyville and within 5km of Lambs Farm and Pine Meadow Golf Club, offers convenient access to local attractions and Libertyville Station. The 182 square metre property boasts four bedrooms, two bathrooms, sleeps ten guests, and includes a fully equipped kitchen, garden, free Wi-Fi, and parking.
9.8 137 reviews
Highland Park, IL
15/08 – 15/09
SG$589/nighttotal: SG$18259 (31 )
Rejuvenate And Relax In The North Shore
1 2
apartment , Highland Park
This four-bedroom apartment in Highland Park is conveniently located just a short distance from Lake Michigan, the Chicago Botanical Garden, and Ravinia Festival, offering easy access to these attractions. It has received excellent ratings for its location, cleanliness, and user experience. The property comfortably accommodates up to 12 guests and features a large yard with outdoor furniture and a propane BBQ grill. Guests can enjoy amenities such as air hockey, darts, and board games, as well as a fully equipped kitchen with a fridge, microwave, dishwasher, and access to the entire home, including the garage.
9.6 4 reviews
Highland Park, IL
15/08 – 15/09
SG$327/nighttotal: SG$10137 (31 )
Home In Dt Libertyville Great For Navy Graduations
2 2
apartment , Libertyville
This Libertyville apartment, conveniently located near Libertyville's town centre and train station, offers easy access to Chicago and Milwaukee, and lies 13km from the Great Lakes Naval Training Center. The two-bedroom, two-bathroom flat sleeps six guests comfortably, boasting a fully equipped kitchen with dishwasher, fast Wi-Fi, Roku TV, and keyless entry; nearby attractions include Six Flags Great America, Lake Michigan beaches, and the Cuneo Mansion and Gardens.
Highland Park, IL
15/08 – 15/09
SG$194/nighttotal: SG$6014 (31 )
Stylish 1 Bedroom Apartment 2 Stops To Naval Base!
1 2
apartment , Highwood
This ground-floor flat is situated in central Highwood, a short walk to Highwood station for transit to Chicago (56 kilometres away by train) and a 32-kilometre drive to the Great Lakes Naval Base. This accommodation for four guests offers a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, air conditioning, high-speed internet, YouTube TV, and includes parking for one car, with a complimentary Graduate Family Pizza Night offered on Thursdays.
Highland Park, IL
11/07 – 14/07
SG$332/nighttotal: SG$996 (3 )
Cozy Studio W/ Breakfast | Business Center & Pool
1 2
studio , Glenview
This aparthotel in Glenview is located 1.8 kilometres from The Glen Town Centre and Kohl Children's Museum, and 3.2 kilometres from The Glen Club. The studio offers space for two guests with a fully equipped kitchen, complimentary breakfast buffet, indoor swimming pool, 24-hour fitness centre, and on-site parking.
Highland Park, IL
15/08 – 15/09
SG$209/nighttotal: SG$6479 (31 )
Stylish 1 Bedroom Apartment 2 Stops To Naval Base!
2 2
apartment , Highwood
This centrally located, first-floor flat in downtown Highwood offers convenient access to Highwood train station, with Great Lakes Naval Base a mere 3.2 kilometres away. This 62 square metre apartment accommodates four guests, featuring two bedrooms, one bathroom, a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, internet, YouTube TV, and on-site parking for one vehicle, plus a complimentary Graduate Family Pizza Night for Navy graduate families.
Highland Park, IL
15/08 – 15/09
SG$476/nighttotal: SG$14756 (31 )
Cozy 4bd 2ba Home Near Downtown / Metra
1 2
apartment , Highland Park
This family-friendly flat in Highland Park is ideally located just a short walk from the Metra station, providing easy access to downtown Highwood and Highland Park's shops and eateries. This property accommodates up to eight guests across four bedrooms, featuring brand-new flooring, central air conditioning, and an open-plan living area for comfortable stays.
9.0 2 reviews
Highland Park, IL
15/08 – 15/09
SG$354/nighttotal: SG$10974 (31 )
Northbrook Rental
1 2
apartment , Northbrook
This three-bedroom apartment is situated in a suburban area of Chicago, just 22 minutes from O'Hare Airport and 25 minutes from the city centre. The apartment is conveniently located for exploring both the city and the surrounding areas. The home provides comfortable accommodation for up to six guests, with two bathrooms and space for an air mattress. It is fully equipped with everything you need for a relaxing stay, including a well-stocked kitchen, a garden, and a range of entertainment options such as multiple TVs, a sound bar, and a selection of games.
Highland Park, IL
15/08 – 15/09
SG$254/nighttotal: SG$7874 (31 )
56 M² Apartment ∙ 1 Bedroom ∙ 2 Guests
1 2
apartment , Evanston
This one-bedroom flat is located in Evanston, a suburb 19 kilometres north of downtown Chicago, near Northwestern University. This 56 square metre flat accommodates two guests and includes a fully equipped kitchen, contemporary furnishings, superior quality mattresses, a premium wireless speaker, a smart TV, on-site laundry facilities, and parking, with flexible lease options available.
Highland Park, IL
15/08 – 15/09
SG$318/nighttotal: SG$9858 (31 )
Charming 3-bedroom House With Ac And Wifi In Wilmette
3 2
apartment , Wilmette
This Wilmette flat offers easy access to schools, the I-94 motorway, public transport, and the town centre, with proximity to the North Shore Centre for the Performing Arts and Skokie Theatre, and shopping at The Glen Town Center and Golf Mill Shopping Centre. This 3-bedroom, 1-bathroom property accommodates up to 6 guests and features a screen porch, a large fenced garden, an attached garage, a wood-burning fireplace, and vaulted ceilings in the kitchen, all ideal for family stays with pets.
Best family friendly Highland Park, IL holiday rentals
Among the 32 accommodations in Highland Park, IL, here are the 4 best family friendly rentals
10 4 reviews
Highland Park, IL
15/08 – 15/09
SG$567/nighttotal: SG$17577 (31 )
Cozy Highwood Apt 4 Br 2 Train Stops To Naval Base
1 2
apartment , Highwood
This Highwood flat is centrally located downtown, a short walk to the train station and a 20-minute drive to the Great Lakes Naval Base. This spacious flat accommodates up to 11 guests, offering four bedrooms, a sofa sleeper, a fully equipped kitchen with a fridge, microwave, and dishwasher, on-site parking for two cars, and YouTube TV for entertainment, with attractions such as Six Flags, Lake Michigan beaches, and forest preserves nearby.
Highland Park, IL
15/08 – 15/09
SG$472/nighttotal: SG$14632 (31 )
3 Bed Home In Dt Highwood - 2 Stops To Navy Base!
4 2
apartment , Highwood
This Highwood flat is situated in the town centre, a short walk from Highwood train station with a 35-minute express service to downtown Chicago, and a 20-kilometre drive to the Great Lakes Naval Base. This 112 square metre apartment accommodates up to 11 guests, offering two full kitchens, high-speed internet with YouTube TV, and complimentary Graduate Family Pizza Night for Navy graduate families, with parking for up to three cars.
Highland Park, IL
15/08 – 15/09
SG$241/nighttotal: SG$7471 (31 )
Cozy Apartment In Dt Libertyville, Near Naval Base
1 2
apartment , Libertyville
This one-bedroom flat is situated in downtown Libertyville, 100 metres from Libertyville Train Station and a short walk from Main Street Libertyville, offering convenient access to Lambs Farm, located 5 kilometres away. The accommodation accommodates up to two guests and features a fully equipped kitchen with a fridge, microwave oven, and dishwasher, as well as air conditioning, Wi-Fi, and a garden with barbecue facilities.
Highland Park, IL
11/07 – 14/07
SG$271/nighttotal: SG$813 (3 )
Condo ∙ 1 Bedroom ∙ 2 Guests
1 2
apartment , Glenview
This Glenview apartment, situated in The Glen business district, offers convenient access to Gallery Park and Meadowhill Park. The one-bedroom, one-bathroom flat sleeps two guests and includes free Wi-Fi, parking, a fully equipped kitchen, and access to a seasonal indoor pool and 24-hour fitness centre within the Staybridge complex.
Best Highland Park, IL holiday rentals with parking
9.6 51 reviews
Highland Park, IL
15/08 – 15/09
SG$453/nighttotal: SG$14043 (31 )
Serene Retreat Awaits You!
4 2
apartment , Highland Park
This spacious four-bedroom apartment is located in Highland Park, just a short distance from Lake Michigan, the Chicago Botanical Garden, and the Ravinia Festival. It has received excellent user ratings and is ideal for families or groups of friends. The property offers a comfortable and well-equipped living space with a large capacity for up to 12 guests. It features a fully equipped kitchen, a garden, a spa, and secure parking, as well as a convenient location for exploring the local attractions and enjoying the many activities available in the area.
9.2 24 reviews
Highland Park, IL
15/08 – 15/09
SG$419/nighttotal: SG$12989 (31 )
Dt Libertyville Home W/ Arcade Pacman By Navy Base
4 2
apartment , Libertyville
This apartment is located in Libertyville’s town centre, just a short walk from the Metra train station and within easy reach of Chicago (80km north) and Milwaukee (80km south). It has received excellent reviews from previous guests, making it a popular choice for travellers. The apartment is a spacious property with four bedrooms and two bathrooms, comfortably accommodating up to ten guests. Guests can enjoy a range of amenities including a well-equipped kitchen, a terrace, a tennis court, and a parking space.
8.8 16 reviews
Highland Park, IL
15/08 – 15/09
SG$260/nighttotal: SG$8060 (31 )
Entire Beautiful Grove Home
3 2
apartment , North Chicago
This fully furnished three-bedroom home is located in a convenient North Chicago neighbourhood, within a 10-15 minute drive of shopping, dining, and entertainment options. The apartment has received very good user ratings, and excellent location and cleanliness ratings. This spacious property provides ample room for up to six guests, with three bedrooms, a living room, dining room, and family room. The apartment offers a range of amenities, including a fully equipped kitchen, air conditioning, a garden, parking, and internet access.
10 1 review
Highland Park, IL
15/08 – 15/09
SG$484/nighttotal: SG$15004 (31 )
Highwood Haven- 4 Bedroom Steps To Train Station!
4 2
apartment , Highwood
This centrally located, cosy second-floor flat in downtown Highwood offers convenient access to Highwood train station, just 3.2 kilometres from Great Lakes Naval Base, and sits midway between Chicago and Milwaukee. This accommodation comfortably sleeps up to 11 guests, featuring four bedrooms, two bathrooms, a fully equipped kitchen with a microwave and dishwasher, air conditioning in all rooms, and on-site parking for two cars, with Highwood train station a short walk away for a 56-kilometre journey to downtown Chicago.
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?
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.
Destinations nearby
Best Highland Park, IL holiday rentals with a balcony
10 1 review
Highland Park, IL
11/07 – 14/07
SG$2033/nighttotal: SG$6099 (3 )
1 Mi To Metra: Estate W/ Theater, Game Room & More
4 2
apartment , Northbrook
This Northbrook holiday let is situated 3.2 kilometres from Glen Town Centre, offering convenient access to local shopping plazas, the Northbrook Metra Station for Chicago transit, and attractions such as the Chicago Botanic Garden. This expansive 864 square metre residence accommodates up to eight guests, featuring four bedrooms, seven bathrooms, a home cinema, a games room with a pool table, a dedicated children's play area, a private home gym, and a large garden with outdoor seating and a fire pit.
Highland Park, IL
15/08 – 15/09
SG$140/nighttotal: SG$4340 (31 )
Charming 1-bedroom Apartment With Wifi, Ac In Glenview, Great School District
1 2
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.
Highland Park, IL
11/07 – 14/07
SG$2048/nighttotal: SG$6144 (3 )
1 Mi To Metra: Estate W/ Theater, Game Room & More
4 2
house , Northbrook
This Northbrook estate offers convenient access, situated 22 kilometres from Loyola University Chicago and 29 kilometres from Wrigley Field, with further transport links via the Metra for Chicago attractions and a 21 kilometre journey to Chicago O'Hare International Airport. This expansive 883 square metre residence accommodates up to 15 guests, featuring a fully equipped kitchen, air conditioning, a balcony, seven bathrooms, a dedicated theatre, a game room, and an outdoor dining area, ensuring a comfortable stay with ample entertainment options.
Best pet friendly Highland Park, IL holiday rentals
Among the 32 accommodations in Highland Park, IL, here are the 4 best pet friendly rentals
This Highland Park studio flat is situated in the Rivinia business district, 0.5km from the Metra station, under 1.6km from Lake Michigan, and 3.2km from the Chicago Botanic Garden. The second-floor, pet-friendly self-catering unit sleeps two, includes free parking, a stocked kitchen (minus a dishwasher), shared laundry facilities, and is within easy reach of the lake and Botanic Garden.
9.4 14 reviews
Highland Park, IL
15/08 – 15/09
SG$296/nighttotal: SG$9176 (31 )
Cozy 2 Bed Apt- 2 Train Stops To The Naval Base!
2 2
apartment , Highwood
This Highwood apartment, a short walk from the train station offering easy access to Chicago and the Great Lakes Naval Training Center, is ideally located for exploring both city and coastal attractions. Sleeping up to seven guests, this two-bedroom, one-bathroom dwelling boasts a fully equipped kitchen with a dishwasher, YouTube TV, high-speed internet, and parking for two cars; nearby attractions include Six Flags Great America and Lake Michigan beaches.
Highland Park, IL
15/08 – 15/09
SG$360/nighttotal: SG$11160 (31 )
Highwood Haven- 4 Bedrooms Steps To Train Station!
1 2
apartment , Highwood
This centrally located, two-bedroom flat in Highwood offers excellent walkability to local amenities and is situated within 500 meters of the Highwood train station, providing direct access to the Great Lakes Naval Base just two stops away. This Highwood accommodation accommodates up to 11 guests with four bedrooms, two bathrooms, a fully equipped kitchen, air conditioning, and two dedicated parking spaces, alongside high-speed internet and YouTube TV.
Highland Park, IL
15/08 – 15/09
SG$236/nighttotal: SG$7316 (31 )
Charming 2-bedroom Apartment In Delightful Highwood 2 Minutes To Train Station!
2 2
apartment , Highwood
This Highwood apartment, situated near Highwood train station offering a 35-minute express train journey to downtown Chicago, provides easy access to both Chicago and Milwaukee. The 65 square metre, two-bedroom flat sleeps up to seven guests, boasting a fully equipped kitchen, high-speed internet, YouTube TV, on-site parking for two cars, and air conditioning throughout; pets are welcome for a £8 per pet, per night fee.