Best Holiday rentals and Airbnb offers in Highland Park, IL
Highland Park, IL
30/07 – 02/08
SG$4831/nighttotal: SG$14493 (3 )
Contemporary House With Partial Lake Views/quiet And Private Area/gut Reno/2023
4 2
apartment , Lake Forest
This Lake Forest holiday home is situated within 1.6km of Lake Forest College and Lake Michigan, and within 4.8km of Forest Park Beach and Northwestern Lake Forest Hospital. This four-bedroom, five-bathroom property sleeps eight guests and boasts a jacuzzi, in-house laundry facilities, and is close to Lake Michigan's beaches.
9.4 6 reviews
Highland Park, IL
15/08 – 15/09
SG$273/nighttotal: SG$8463 (31 )
Downtown Libertyville Apt Near Naval Base
2 2
apartment , Libertyville
This two-bedroom apartment is conveniently situated in the heart of Libertyville, just a short walk from the town's main street and within easy reach of restaurants, shops and events. It's approximately 80 kilometres north of Chicago and 160 kilometres south of Milwaukee, making it an ideal base for exploring the area. This property has received excellent guest reviews, highlighting its comfortable and well-equipped nature. The apartment offers a spacious living area, perfect for families or groups of up to six guests. Amenities include a fully equipped kitchen, air conditioning, free high-speed internet, parking and a convenient location near attractions such as Six Flags Great America, Lambs Farm, the Lake County Fairgrounds and the Chain of Lakes.
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$254/nighttotal: SG$7874 (31 )
56 M² Apartamento ∙ 1 Quarto ∙ 2 Hóspedes
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.
9.6 9 reviews
Highland Park, IL
15/08 – 15/09
SG$321/nighttotal: SG$9951 (31 )
Cozy Modern Studio Near Ravinia W/free Parking
1 2
apartment , Highland Park
This newly renovated studio apartment is located in downtown Highland Park, a short walk from Ravinia Festival and less than 2 kilometres from Lake Michigan. This well-appointed flat offers accommodation for two guests, featuring a queen bed, a fully equipped kitchen with a dishwasher, and free parking, with direct train access to Chicago just 800 metres away.
9.9 42 reviews
Highland Park, IL
28/08 – 30/08
SG$1179/nighttotal: SG$2358 (2 )
North Shore Blue-door Bungalow
3 2
apartment , Highland Park
This charming bungalow is located in Highland Park, just under 1.6 kilometres from Highland Park Hospital and Uptown Highland Park, offering easy access to amenities, green spaces and a peaceful setting across from Sunset Park. The house has three bedrooms and one bathroom, comfortably accommodating up to four guests. It features a fully equipped kitchen, air conditioning, parking, internet access, and a welcoming atmosphere for families and pets.
8.7 3 reviews
Highland Park, IL
02/08 – 04/08
SG$686/nighttotal: SG$1372 (2 )
Charming Contemporary Family Home
3 2
house , Glenview
This Glenview home is situated just 19 kilometres from Loyola University Chicago and 23 kilometres from Wrigley Field, making it a convenient base for exploring the area. The property has received consistently high ratings for location, cleanliness, and overall experience. The 3-bedroom property offers 111 square metres of space and comfortably accommodates up to 6 guests. This family-friendly home features air conditioning, free Wi-Fi, a fully equipped kitchen, a washing machine, and a patio, making it ideal for a relaxing and enjoyable stay.
9.6 20 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.
Highland Park, IL
15/08 – 15/09
SG$316/nighttotal: SG$9796 (31 )
Comfort In Highwood- 4 Brs & Steps To The Train!
1 2
apartment , Highwood
This 1st-floor flat is situated in the centre of Highwood, a short walk from Highwood station, offering easy access to Chicago. This property accommodates up to 11 guests, featuring a fully equipped kitchen, high-speed internet, air conditioning in all rooms, and on-site parking for two vehicles.
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
02/07 – 09/07
SG$244/nighttotal: SG$1708 (7 )
Studio Flat ∙ 1 Bedroom ∙ 2 Guests
1 2
studio , Glenview
This Glenview studio apartment is situated in The Glen business district, conveniently close to Northwestern University and approximately 8km from both the Kohl Children's Museum and the Illinois Holocaust Museum. The self-catering unit sleeps two guests, offering a fully equipped kitchen, complimentary breakfast (Monday-Wednesday), an on-site fitness centre, indoor pool, and free parking; evening receptions (Monday-Wednesday) with food and drinks are also provided.
Best family friendly Highland Park, IL holiday rentals
Among the 32 accommodations in Highland Park, IL, here are the 4 best family friendly rentals
9.6 8 reviews
Highland Park, IL
15/08 – 15/09
SG$332/nighttotal: SG$10292 (31 )
Lovely Duplex In Dt Libertyville Near Naval Base!
3 2
apartment , Libertyville
This three-bedroom flat is located in the centre of Libertyville, a lively town with a range of shops and restaurants, just 60km north of Chicago and 60km south of Milwaukee. It has received excellent guest reviews and is perfect for families or groups looking for a comfortable and convenient base to explore the area. The flat has one bathroom and can comfortably accommodate up to eight guests. It is well-equipped with a modern kitchen, a garden, free Wi-Fi, and parking, as well as a range of amenities including a Keurig coffee maker, a crockpot, and a Roku TV.
8.8 39 reviews
Highland Park, IL
28/08 – 30/08
SG$305/nighttotal: SG$610 (2 )
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.
9.8 31 reviews
Highland Park, IL
02/07 – 09/07
SG$2352/nighttotal: SG$16464 (7 )
6 Bedrooms Home Suburbs Of Chicago
6 2
apartment , Glenview
This spacious property is located in Glenview, just a 5-10 minute drive from local supermarkets. It has received excellent ratings for its cleanliness, location and user experience. The house has 6 bedrooms and 5.5 bathrooms, comfortably accommodating large families or groups of friends. Guests can enjoy a range of amenities including a home theatre, gym, jacuzzi, garden, and a large BBQ and dining area.
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 Highland Park, IL holiday rentals with parking
Highland Park, IL
15/08 – 15/09
SG$378/nighttotal: SG$11718 (31 )
4br, 3ba, Home Evanston, Il, Near Northwestern Univ, Fully Furnished, Equipped
4 2
apartment , Evanston
This Evanston property is situated a short distance (under 1.6 km) from Northwestern University, Lake Michigan, Welsh-Ryan Arena, and the Baháʼà House of Worship, offering easy access to public transport (Central and Noyes stations). Sleeping up to five guests, this four-bedroom, three-bathroom house boasts a fully equipped kitchen, Jacuzzi, garden, parking, and WiFi; nearby activities include exploring the lakefront and visiting the university campus.
10 5 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.
10 3 reviews
Highland Park, IL
15/08 – 15/09
SG$739/nighttotal: SG$22909 (31 )
Luxury Home With Awesome Master Bathroom & Huge Back Yard
4 2
apartment , Niles
This apartment is located in Niles, just 15 kilometres from four major shopping centres, 12 kilometres from the airport, and 40 kilometres from the centre of Chicago. It is also within walking distance of local restaurants and a bar, making it a convenient base for exploring the area. The apartment has consistently received excellent reviews from previous guests. This spacious apartment spans 372 square metres and can comfortably accommodate up to 10 guests. It boasts a range of amenities including a fully equipped kitchen, a master bathroom with a 32-inch TV, and a secret Harry Potter door leading to a game room, a movie theatre, and a fully heated garage with a gym.
9.5 15 reviews
Highland Park, IL
02/08 – 04/08
SG$158/nighttotal: SG$316 (2 )
1 King Bed | Non-smoking, Kitchen, Shower
1 2
apartment , Vernon Hills
This Mettawa residence is situated 27 kilometres from Chicago O'Hare International Airport and 20 kilometres from Six Flags Great America. This 28 square metre flat offers accommodation for up to two guests, featuring air conditioning, a fully equipped kitchen with a fridge and microwave, complimentary WiFi, on-site parking, and a sofa bed, with a dining area and a work desk for added convenience.
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
8.7 1223 reviews
Highland Park, IL
02/08 – 04/08
SG$264/nighttotal: SG$528 (2 )
Lincolnshire Marriott Resort
1 2
resort , Lincolnshire
The Lincolnshire Marriott Resort is located in Lincolnshire, just a 30-minute drive from O'Hare International Airport. The resort has consistently received very good ratings for its location, cleanliness, and overall experience. The hotel has a variety of amenities, including an 18-hole golf course, an award-winning theatre, five restaurants, an indoor and outdoor pool, a fitness centre, and a spa. Guests can also enjoy tennis courts, a garden, a terrace, and room service.
10 21 reviews
Highland Park, IL
28/08 – 30/08
SG$1145/nighttotal: SG$2290 (2 )
"Faith Of Evanston" 180°view, 2bdr +2bath Urban Luxury
2 2
apartment , Evanston
This Evanston apartment is situated 2.1 kilometres from Lake Michigan and Northwestern University, offering easy access to Davis Metro Station and Evanston Davis Street Station. The two-bedroom, two-bathroom flat sleeps five guests and boasts a fully equipped kitchen, private balcony, in-unit fireplace, access to a swimming pool and fitness centre, and free Wi-Fi.
10 21 reviews
Highland Park, IL
28/08 – 30/08
SG$1043/nighttotal: SG$2086 (2 )
"Hope Of Evanston" 180°view, 2bdr +2bath Urban Luxury
2 2
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.
10 33 reviews
Highland Park, IL
28/08 – 30/08
SG$1057/nighttotal: SG$2114 (2 )
"Bliss Of Evanston" 180°view, 2bdr +2bath Urbanlux
2 2
apartment , Evanston
This two-bedroom apartment is located in Evanston, just 1.3 kilometres from Northwestern University and 1.3 kilometres from Lake Michigan, offering easy access to both the university and the beach. This highly-rated property has received excellent reviews from previous guests. The apartment provides 116 square metres of space, accommodating up to five guests. It features a modern kitchen, a balcony, a fitness centre, and a swimming pool, ensuring a comfortable and enjoyable stay.
Best pet friendly Highland Park, IL holiday rentals
Among the 32 accommodations in Highland Park, IL, here are the 4 best pet friendly rentals
10 1 review
Highland Park, IL
15/08 – 15/09
SG$404/nighttotal: SG$12524 (31 )
Cozy 3 Bedroom In Dt Libertyville Near Naval Base!
1 2
apartment , Libertyville
This four-bedroom, one-bathroom Libertyville apartment is conveniently located a 0.8 km walk from MainStreet Libertyville and a 4 km drive from Lambs Farm. The self-catering property offers covered parking, a private garden with barbecue facilities, in-unit laundry, and amenities including Wi-Fi, a fireplace, and air conditioning, comfortably accommodating a family.
Highland Park, IL
02/08 – 04/08
SG$402/nighttotal: SG$804 (2 )
Skokie 1br Stay Near Parks, Dining & Transit
1 2
apartment , Skokie
This Skokie apartment is situated a 2.25km walk from the North Shore Center for the Performing Arts and an 12.8km drive from Lake Michigan. The two-bedroom, one-bathroom flat sleeps two guests and offers Wi-Fi, a fully equipped kitchen including a dishwasher, and is close to Norridge Park District and Northbrook Sports Complex.
9.8 24 reviews
Highland Park, IL
28/06 – 05/07
SG$370/nighttotal: SG$2590 (7 )
Great For Families Dt Libertyville Near Naval Base
3 2
apartment , Libertyville
This Libertyville apartment, situated within walking distance of Libertyville's town centre and approximately 13 kilometres from the Great Lakes Naval Base, offers easy access to the Metra train station and local attractions. The newly remodelled, two-storey property sleeps eight guests in two king-size beds, one queen-size bed, two twin roll-away beds, and a sofa bed, boasting a fully equipped kitchen, fast Wi-Fi, Roku TV with streaming services, and keyless entry.
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.
