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Highland Park, IL vacation rentals
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Best Vacation rentals and Airbnb offers in Highland Park, IL

Top Vacation Rentals for Families in Highland Park, IL

These kid-friendly vacation rentals in Highland Park, IL keep you close to top city attractions for a stress-free family vacation.

Home In Dt Libertyville Near Corp Hqs & Naval Base - Highland Park, IL
9.6 14 reviews
Highland Park, IL
08/15 – 09/15
$383/nighttotal: $11873 (31 )

Home In Dt Libertyville Near Corp Hqs & Naval Base

4 2
apartment , Libertyville
This Libertyville apartment is located in downtown, within walking distance of the Metra train station, restaurants, shops, and other downtown attractions. This makes it a great choice for travelers who want to be close to the action.
The apartment has four bedrooms and two bathrooms, comfortably accommodating up to 12 guests. It comes equipped with a full kitchen, a Keurig coffee maker, free Wi-Fi, a Roku TV, and other modern amenities.
Navy Retreat Near Naval Base-tiki Bar,sauna,games - Highland Park, IL
10 26 reviews
Highland Park, IL
08/15 – 09/15
$375/nighttotal: $11625 (31 )

Navy Retreat Near Naval Base-tiki Bar,sauna,games

4 2
apartment , North Chicago
This North Chicago vacation rental is a 3-minute drive from Lake Michigan and a 4-minute drive from the Genesee Theatre, offering convenient access to the North Chicago Metra station and various attractions including Six Flags Great America and Waukegan Harbor.
This four-bedroom, two-bathroom home sleeps eleven guests and includes a fully equipped kitchen with dishwasher and microwave, in-unit laundry, Wi-Fi, air conditioning, on-site parking, and a garden with barbecue facilities.
The Pleasant Hill Cottage North Shore Enchantment - Highland Park, IL
10 6 reviews
Highland Park, IL
08/15 – 09/15
$509/nighttotal: $15779 (31 )

The Pleasant Hill Cottage North Shore Enchantment

1 2
apartment , Highwood
This Highwood cottage, a short drive from Lake Michigan beaches, the Ravinia Festival, and the Chicago Botanic Garden, offers easy access to Chicago via train.
The 12-room rental boasts 3.5 bedrooms, 2.5 bathrooms, a basement bonus room, on-site parking for two vehicles, plus family-friendly amenities including beach toys, games, and a fire pit, accommodating up to 10 guests.
Cozy Apartment In Dt Libertyville, Near Naval Base - Highland Park, IL
Highland Park, IL
08/15 – 09/15
$187/nighttotal: $5797 (31 )

Cozy Apartment In Dt Libertyville, Near Naval Base

1 2
apartment , Libertyville
This one-bedroom, one-bathroom apartment is located in downtown Libertyville, a 10-minute walk from the Libertyville train station and a 5-minute drive from Lambs Farm.
This pet-friendly rental offers Wi-Fi, air conditioning, a full kitchen with a microwave and dishwasher, and barbecue facilities in the garden, accommodating up to two guests.

Best Highland Park, IL vacation rentals with parking

Cozy Highwood Apt 4 Br 2 Train Stops To Naval Base - Highland Park, IL
10 4 reviews
Highland Park, IL
08/15 – 09/15
$441/nighttotal: $13671 (31 )

Cozy Highwood Apt 4 Br 2 Train Stops To Naval Base

1 2
apartment , Highwood
This 4-bedroom, 1-bathroom rental in downtown Highwood is located a 5-minute walk from the Highwood train station, offering express service to Chicago in 35 minutes, and is a 20-minute drive or two train stops from the Great Lakes Naval Base.
This 1st-floor apartment accommodates up to 11 guests with a pull-out sofa, features a full kitchen with a fridge, microwave, and dishwasher, air conditioning, YouTube TV, and on-site parking for two cars.
Cozy 2 Bed Apt- 2 Train Stops To The Naval Base! - Highland Park, IL
9.4 3 reviews
Highland Park, IL
08/15 – 09/15
$217/nighttotal: $6727 (31 )

Cozy 2 Bed Apt- 2 Train Stops To The Naval Base!

2 2
apartment , Highwood
This Highwood apartment rental is conveniently located downtown, a short walk from the train station offering a 35-minute express train ride to Chicago and a short drive from the Great Lakes Naval Base.
This 740-square-foot two-bedroom, one-bathroom dwelling sleeps up to seven guests and features a fully equipped kitchen, YouTube TV, high-speed internet, parking for two cars, and air conditioning.
Highwood Haven- 4 Bedroom Steps To Train Station! - Highland Park, IL
10 1 review
Highland Park, IL
08/15 – 09/15
$377/nighttotal: $11687 (31 )

Highwood Haven- 4 Bedroom Steps To Train Station!

4 2
apartment , Highwood
This apartment rental is located in downtown Highwood, a 4-minute drive from Lake Michigan and an 11-minute drive from Park Avenue Boating-Fishing Beach, with Highwood Station accessible within a 9-minute walk.
This 4-bedroom, 2-bathroom rental accommodates up to 11 guests and features on-site parking, a full kitchen with an oven and microwave, in-unit laundry, air conditioning, and Wi-Fi, with proximity to Ravinia Green Country Club and Conway Farms Golf Club.
1 Mi To Metra: Estate W/ Theater, Game Room & More - Highland Park, IL
Highland Park, IL
07/11 – 07/14
$1593/nighttotal: $4779 (3 )

1 Mi To Metra: Estate W/ Theater, Game Room & More

4 2
house , Northbrook
This Northbrook house is situated 14 miles from Loyola University Chicago and 18 miles from Wrigley Field, with proximity to Metra Estate and its entertainment options.
This 9,500 square foot vacation home accommodates up to 15 guests with 7 bathrooms, a fully equipped kitchen, air conditioning, WiFi, a balcony, a theater, and a game room.

Frequently Asked Questions about vacation rentals in Highland Park, IL

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

    Highland Park has a lot to offer families! The Highland Park Zoo is a great place to see animals, and the Park Avenue Summerfest is a popular event with family-friendly activities. You can also enjoy the Highland Park Public Library, which has a great children's section.
  • What are the best Airbnb and vacation rentals in Highland Park, IL?

    2-acre Highland Park Retreat With Heated Pool ~ 5*, Guest Room With 1 King Bed and Adorable Carriage House East Lake Forest 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 in Highland Park is during the summer months, when the weather is warm and the lakefront is bustling. Keep in mind that prices tend to be higher during peak season, so you might want to book in advance.
  • What are the most popular Airbnbs in Highland Park, IL?

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

    Highland Park has plenty of free and inexpensive things to do. Take a walk along the lakefront, visit the Highland Park Public Library, or explore the Highland Park Historical Society. You can also pack a picnic and enjoy a meal at one of the many parks in the area.
  • What are the best vacation rentals with a pool in Highland Park, IL?

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

    Highland Park has a diverse culinary scene, but for local dishes, try The Grill on Green Bay for classic American fare, The Cottage for a cozy atmosphere and delicious comfort food, or The Purple Pig for modern American cuisine.
  • What are the best rentals for families and kids 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 that runs along the shores of Lake Michigan. You can also enjoy a scenic ride through the streets of downtown Highland Park or explore the North Shore Bike Path, which connects several towns north of Chicago.
  • What are the best rentals or Airbnbs with a jacuzzi in Highland Park, IL?

    The best vacation rentals or Airbnb with a jacuzzi in Highland Park, IL are Luxury 5br With Pool & Theater, Luxe Mansion For Serene Retreat and Lovely 1 Bedroom In Highland Park.

  • Are there pet-friendly attractions in Highland Park, IL?

    Highland Park is very dog-friendly. Many of the parks and restaurants welcome pets, and the Lakefront Trail is a great place to take your dog for a walk. You can also check out the Highland Park Dog Park for some off-leash fun.
  • What are the benefits of choosing a vacation rental in Highland Park, IL?

    Vacation rentals offer more space and privacy than a hotel room, and they often come with amenities like a kitchen and laundry facilities. They can also be a more affordable option, especially if you're traveling with a family or group.
  • What are the top sports attractions and facilities in Highland Park, IL?

    Highland Park is home to the Highland Park Sports Complex, which offers a variety of sports facilities, including baseball fields, tennis courts, and a swimming pool. You can also check out the Highland Park Golf Club for a round of golf.

Destinations nearby

Best Vacation Rentals with Balconies in Highland Park, IL

Enjoy a Highland Park, IL vacation rental with a balcony and stunning city skyline views for a truly memorable stay.

Home In Dt Libertyville Great For Navy Graduations - Highland Park, IL
9.6 4 reviews
Highland Park, IL
08/15 – 09/15
$254/nighttotal: $7874 (31 )

Home In Dt Libertyville Great For Navy Graduations

2 2
apartment , Libertyville
This Libertyville apartment rental is conveniently located within walking distance of downtown Libertyville and the Metra train station, offering easy access to Chicago and Milwaukee, and an 8-mile drive from the Great Lakes Naval Training Center.
This two-bedroom, two-bathroom unit sleeps six guests comfortably, boasting a fully equipped kitchen with a Keurig coffee maker, fast Wi-Fi, Roku TV with streaming apps, keyless entry, and a dedicated workspace; nearby attractions include Six Flags Great America, Lake Michigan beaches, and the Bess Bower Dunn Museum.

Our Favorite Pet-Friendly Vacation Rentals in Highland Park, IL

Discover pet-friendly vacation rentals in Highland Park, IL that prioritize comfort for both you and your dog.

Great For Families Dt Libertyville Near Naval Base - Highland Park, IL
9.6 25 reviews
Highland Park, IL
08/15 – 09/15
$276/nighttotal: $8556 (31 )

Great For Families Dt Libertyville Near Naval Base

3 2
apartment , Libertyville
This 3-bedroom, 2-bathroom apartment is located in the heart of Libertyville, within walking distance of trendy restaurants, shops, and the Metra train station. The apartment can accommodate up to 10 guests and features a fully equipped kitchen, air conditioning, and keyless entry.
Guests will enjoy access to a Roku TV with YouTube TV and Netflix access, fast, dedicated Wi-Fi, a desk and chair, a wireless printer, and board games for entertainment. The apartment is also conveniently located halfway between Chicago and Milwaukee, making it a great base for exploring the region.
Serene Retreat Awaits You! - Highland Park, IL
9.6 51 reviews
Highland Park, IL
08/15 – 09/15
$352/nighttotal: $10912 (31 )

Serene Retreat Awaits You!

4 2
apartment , Highland Park
This spacious four-bedroom apartment is located in Highland Park, close to Lake Michigan, the Chicago Botanical Garden, and downtown Chicago, making it an ideal base for exploring the area. The apartment has received excellent ratings from previous guests, highlighting its comfort and convenience.
This apartment has four bedrooms and three bathrooms, accommodating up to 12 guests comfortably. The apartment offers a range of amenities, including a fully equipped kitchen, a garden, a spa, and parking, ensuring a comfortable and enjoyable stay.
Comfort In Highwood- 4 Brs & Steps To The Train! - Highland Park, IL
Highland Park, IL
08/15 – 09/15
$246/nighttotal: $7626 (31 )

Comfort In Highwood- 4 Brs & Steps To The Train!

1 2
apartment , Highwood
This 4-bedroom, 1-bathroom condo rental is situated directly in downtown Highwood, offering immediate walkability and convenient access to the Highwood Metra train station, which provides a direct commute to Downtown Chicago.
This 1st-floor dwelling comfortably sleeps up to 11 guests, featuring a fully equipped kitchen, air conditioning in all rooms, high-speed internet with YouTube TV, and dedicated parking for two cars, making it an ideal choice for families or groups visiting Highwood.
Furnished Lake Forest 3br Townhome | Monthly - Highland Park, IL
10 13 reviews
Highland Park, IL
08/15 – 09/15
$175/nighttotal: $5425 (31 )

Furnished Lake Forest 3br Townhome | Monthly

1 2
house , Lake Forest
This Lake Forest townhome, near downtown, is a 5-minute walk from Market Square, close to the Metra station, and a short drive from Lake Michigan beaches.
This three-bedroom, two-bathroom duplex sleeps six guests and offers a fully equipped kitchen, in-unit laundry, off-street parking, and a starter supply of toiletries and cleaning supplies.
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