Best Holiday rentals and Airbnb offers in Highland Park, IL
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.
This Highland Park apartment is situated in the Rivinia Business District, offering convenient access to local shops and restaurants. The ground-floor flat, sleeping two guests, boasts a full kitchen with a gas stove and refrigerator, a dedicated workspace with high-speed Wi-Fi, a 55” Samsung smart TV, Xbox One, in-building laundry, and free overnight parking.
10 13 reviews
Highland Park, IL
15/08 – 15/09
SG$225/nightTotal: SG$6975 (31 )
Furnished Lake Forest 3br Townhome | Monthly
1 2
house , Lake Forest
This three-bedroom, two-bathroom townhome is situated in downtown Lake Forest, a short 0.8 km walk from Market Square and close to the Metra station and Lake Michigan beaches. The property offers self-catering facilities including a fully equipped kitchen and in-unit laundry, comfortably accommodating up to six guests with off-street parking and pet-friendly features.
8.0 4 reviews
Highland Park, IL
02/08 – 04/08
SG$251/nightTotal: SG$502 (2 )
Chic Studio In Downtown Highland Park Near Metra
1 2
studio , Highland Park
This studio apartment is located in downtown Highland Park, a 5-minute walk to the Metra station for convenient transport, and a 15-minute walk to Lake Michigan's shores, with Fort Sheridan Forest Preserve and beach a 5-minute drive away. This well-appointed apartment accommodates two guests and offers air conditioning, Wi-Fi, and a kitchen with a fridge and microwave oven, making it ideal for exploring local dining, parks, and cultural attractions such as Ravinia Park.
Highland Park, IL
28/08 – 30/08
SG$195/nightTotal: SG$390 (2 )
Studio Flat ∙ 1 Bedroom ∙ 2 Guests
1 2
studio , Glenview
This Glenview studio apartment is conveniently located near Gallery Park and Meadowhill Park, offering easy access to outdoor recreation. The self-catering unit sleeps two, features a fully equipped kitchen with a fridge, microwave, and dishwasher, plus free Wi-Fi, access to a seasonal indoor pool and 24-hour fitness centre within the Staybridge complex, and benefits from light housekeeping (Monday-Friday) and weekly cleaning.
10 14 reviews
Highland Park, IL
28/08 – 30/08
SG$171/nightTotal: SG$342 (2 )
1 King Bed | Non-smoking, Kitchen
1 2
apartment , Vernon Hills
This Vernon Hills flat, situated on a lake, is 20 kilometres from Six Flags Great America and 27 kilometres from Chicago O'Hare International Airport. This 28 square metre apartment, suitable for two guests, features a double king-size bed, a fully equipped kitchen with a fridge and microwave, air conditioning, free WiFi, and on-site parking, with opportunities for motor boating on the adjacent lake.
10 62 reviews
Highland Park, IL
28/08 – 30/08
SG$719/nightTotal: SG$1438 (2 )
Green Oasis In Law Suite
1 2
apartment , Highland Park
This one-bedroom flat is situated in Highland Park, a short 1.1 kilometre walk from Starbucks, parks, restaurants, dry cleaners and a Jewel supermarket. The apartment features a full kitchen with stainless steel appliances, a private washer and dryer, and a designated parking space in a long driveway, accommodating up to three guests.
10 18 reviews
Highland Park, IL
02/08 – 04/08
SG$149/nightTotal: SG$298 (2 )
Spacious 2 Queen Beds,nsmk|kitchen|studio 6 Vernon Hills
1 2
studio , Vernon Hills
This apartment in Mettawa is located 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 four guests with a Queen bed and sofa bed, featuring a kitchen with fridge and microwave, air conditioning, and free WiFi, situated on the ground floor with a dining area.
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.
9.8 87 reviews
Highland Park, IL
28/08 – 30/08
SG$1001/nightTotal: SG$2002 (2 )
A Wonderful Getaway Home On The North Shore!
1 2
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.
8.8 3 reviews
Highland Park, IL
11/07 – 14/07
SG$748/nightTotal: SG$2244 (3 )
Amazing Mid-term Rental Entire Home In Glenview
3 2
apartment , Glenview
This three-bedroom, two-bathroom Northbrook house, less than 1.6km from Grove National Historic Landmark and NorthShore Glenbrook Hospital, offers convenient access to Glenview attractions. Sleeping eight guests, the property includes a washing machine, hair dryer, and is situated in a quiet suburban setting with easy access to amenities such as The Glen Club (within 4.8km).
Highland Park, IL
02/08 – 04/08
SG$302/nightTotal: SG$604 (2 )
Condo ∙ 1 Bedroom ∙ 2 Guests
1 2
apartment , Glenview
This Glenview apartment is located in The Glen business district, offering easy access to Northwestern University and the Metra station for a quick commute to Chicago city centre, approximately 25km away. The one-bedroom, one-bathroom flat sleeps two guests and includes a fully equipped kitchen, complimentary breakfast (Monday-Wednesday), an evening reception (Monday-Wednesday), a 24-hour fitness centre, and an indoor heated swimming pool, plus free on-site parking.
Best family friendly Highland Park, IL holiday rentals
Among the 32 accommodations in Highland Park, IL, here are the 4 best family friendly rentals
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.
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.
9.0 16 reviews
Highland Park, IL
15/08 – 15/09
SG$520/nightTotal: SG$16120 (31 )
Home W/ Large Deck, Libertyville - Near Naval Base
4 2
apartment , Green Oaks
This five-bedroom Green Oaks house, ideal for large families or groups, offers 169 square metres of living space and sleeps up to 12 guests. The property includes a fully equipped kitchen, two bathrooms, laundry facilities, free Wi-Fi, a garden, and parking; further details regarding its precise location within Green Oaks and proximity to local landmarks are unavailable.
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.
Best Highland Park, IL holiday rentals with parking
10 16 reviews
Highland Park, IL
28/08 – 30/08
SG$670/nightTotal: SG$1340 (2 )
"Joy Of Evanston" 1bdr, King Exec Suite, Pool+gym
1 2
apartment , Evanston
This family-friendly apartment is located in Evanston, close to the river and within a 3km radius of Northwestern University and Lake Michigan. It has received excellent reviews from previous guests. This one-bedroom flat offers 70 square metres of space and can accommodate up to four guests. It features a well-equipped kitchen, a private balcony, a swimming pool, a fitness centre, and free parking, making it ideal for families and groups looking for a comfortable and convenient stay.
Highland Park, IL
15/08 – 15/09
SG$344/nightTotal: SG$10664 (31 )
Furnished Lake Forest 3br Townhome Monthly Housing Near Great Lakes
3 2
apartment , Lake Forest
This Lake Forest holiday home is situated a 0.7km walk from Market Square and a 2.4km drive from Lake Michigan, offering easy access to East Lake Forest train station. The 130 square metre property features three bedrooms, two bathrooms, a fully equipped kitchen with appliances including a dishwasher and microwave, plus Wi-Fi, parking, and is ideal for families or groups.
9.2 46 reviews
Highland Park, IL
28/08 – 30/08
SG$568/nightTotal: SG$1136 (2 )
New Your Home Away From Home! - Near Great Lakes Naval Base!!
4 2
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.
9.9 118 reviews
Highland Park, IL
28/08 – 30/08
SG$1354/nightTotal: SG$2708 (2 )
*King Bed *Outdoor Living *Sought-after Area
1 2
apartment , Northbrook
This newly renovated three-bedroom ranch-style house in Northbrook offers excellent family-friendly accommodation, conveniently located within walking distance of local shops and restaurants; precise distances are not specified. Sleeping eight guests comfortably, the property boasts a fully-equipped kitchen with stainless steel appliances, a large fenced garden with outdoor seating, and family-friendly amenities including a pack-n-play and highchair; high-speed Wi-Fi and driveway parking are also provided.
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 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.
Highland Park, IL
02/08 – 04/08
SG$955/nightTotal: SG$1910 (2 )
Parisian Inspired Escape - Close To Town & Nu
2 2
apartment , Evanston
This two-bedroom flat is located in Evanston's Church & Dodge district, 800 metres from Downtown Evanston and less than 1.6 kilometres from Northwestern University. This family-friendly property offers a gourmet kitchen, a lower-level family room with a movie screen, an office space, a sunny patio, and is close to Lake Michigan for water activities and Michigan Avenue for shopping.
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.
9.9 176 reviews
Highland Park, IL
28/08 – 30/08
SG$549/nightTotal: SG$1098 (2 )
Executively Appointed Condo, W/resort Amenities, Ind Gar, Pool, Gym+ Biz Lounge
2 2
apartment , Evanston
This apartment is located in downtown Evanston, a short walk from Northwestern University, Loyola University, and Kellogg School of Management, and a short train ride from Chicago. It has excellent user, location and cleanliness ratings. This one-bedroom apartment sleeps up to four guests and features a modern kitchen, a comfortable living area, and a private balcony. Amenities include a swimming pool, a fitness centre, a garden, and a terrace, perfect for enjoying the Evanston sunshine.
Best pet friendly Highland Park, IL holiday rentals
Among the 32 accommodations in Highland Park, IL, here are the 4 best pet 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.
9.4 3 reviews
Highland Park, IL
15/08 – 15/09
SG$279/nightTotal: SG$8649 (31 )
Cozy 2 Bed Apt- 2 Train Stops To The Naval Base!
2 2
apartment , Highwood
This Highwood apartment is situated a 6.4km drive from Lake Michigan and a 4.8km drive from Moraine Park, offering easy access to Highwood train station. The 69 square metre self-catering flat comprises two bedrooms, one bathroom, and sleeps up to seven guests, featuring a fully equipped kitchen, in-unit laundry, and free Wi-Fi.
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.
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.
