Holiday Rentals in Highland Park, IL

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

Cozy Highwood Apt 4 Br 2 Train Stops To Naval Base - Highland Park, IL
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.
3 Bed Home In Dt Highwood - 2 Stops To Navy Base! - Highland Park, IL
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.
Cozy Apartment In Dt Libertyville, Near Naval Base - Highland Park, IL
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.
Condo ∙ 1 Bedroom ∙ 2 Guests - Highland Park, IL
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

Serene Retreat Awaits You! - Highland Park, IL
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.
Dt Libertyville Home W/ Arcade Pacman By Navy Base - Highland Park, IL
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.
Entire Beautiful Grove Home - Highland Park, IL
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.
Highwood Haven- 4 Bedroom Steps To Train Station! - Highland Park, IL
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?

    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.

Destinations nearby

Best Highland Park, IL holiday rentals with a balcony

1 Mi To Metra: Estate W/ Theater, Game Room & More - Highland Park, IL
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.
Charming 1-bedroom Apartment With Wifi, Ac In Glenview, Great School District - Highland Park, IL
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.
1 Mi To Metra: Estate W/ Theater, Game Room & More - Highland Park, IL
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

Month-to-month Secure, Charming, Cozy Pied-à-terre - Highland Park, IL
9.8 17 reviews
Highland Park, IL
15/08 – 15/09
SG$156/nighttotal: SG$4836 (31 )

Month-to-month Secure, Charming, Cozy Pied-à-terre

1 2
apartment , Highland Park
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.
Cozy 2 Bed Apt- 2 Train Stops To The Naval Base! - Highland Park, IL
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.
Highwood Haven- 4 Bedrooms Steps To Train Station! - Highland Park, IL
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.
Charming 2-bedroom Apartment In Delightful Highwood 2 Minutes To Train Station! - Highland Park, IL
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.
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