Search vacation rental in Highland Park, IL from 100+ sites!
32 available vacation rental offers
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating
Best Vacation rentals and Airbnb offers in Highland Park, IL
10 49 reviews
Highland Park, IL
08/02 – 08/04
$471/nighttotal: $942 (2 )
Cozy Neighborhood Escape: Near Northwestern-chicago-beaches & More
1 2
apartment , Evanston
This Evanston apartment is in the arts district, close to shops, restaurants, the lakefront, Northwestern University, and major hospitals. Guests have consistently rated this rental excellent. This 1-bedroom, 1-bathroom home comfortably sleeps 4 guests. The apartment includes a full kitchen, a Jacuzzi, a garden, parking, a smart TV, laundry, and free coffee and board games.
10 14 reviews
Highland Park, IL
07/30 – 08/02
$130/nighttotal: $390 (3 )
1 King Bed | Non-smoking, Kitchen, Shower
1 2
apartment , Vernon Hills
This apartment in Mettawa is located 17 miles from Chicago O'Hare International Airport, 12 miles from Six Flags Great America, and 25 miles from Loyola University Chicago. This 300 sq ft studio unit offers a fully equipped kitchen, a sofa bed, free WiFi, and on-site parking, with proximity to Lake Michigan, Oak Ridge Marsh Nature Park, and the Marriott Theatre.
10 16 reviews
Highland Park, IL
06/28 – 07/05
$127/nighttotal: $889 (7 )
Studio 6 Vernon Hills|relax Queen Bed,nsmk|kitchen
1 2
studio , Vernon Hills
This Mettawa studio apartment is located 17 miles from Six Flags Great America and 16.8 miles from Chicago O'Hare International Airport, offering a serene lakefront setting with convenient access to Gurnee Mills and Oak Ridge Marsh Nature Park. This 300 square foot rental accommodates up to 2 guests, featuring air conditioning, free WiFi, free private parking, and a kitchen equipped with a fridge and microwave, with opportunities for motor boating nearby.
10 4 reviews
Highland Park, IL
08/02 – 08/04
$536/nighttotal: $1072 (2 )
Highland Park Residence
4 2
apartment , Highland Park
This 4-bedroom, 3-bathroom rental home in Highland Park offers 10-guest capacity and is located 1.5 miles from the Highland Park Historical Society Museum. This residence features a full kitchen with a fridge, microwave, and dishwasher, air conditioning, a garden, and parking, making it ideal for group travel and exploring the area.
10 13 reviews
Highland Park, IL
08/02 – 08/04
$116/nighttotal: $232 (2 )
Studio 6 Vernon Hills|ada Queen Bed,ri Shower,nsmk|kitchen
1 2
studio , Vernon Hills
This Mettawa studio apartment is located 17 miles from Six Flags Great America and 27 miles from Chicago O'Hare International Airport, offering lakefront access for motor boating and proximity to the Marriott Theatre and Raupp Memorial Museum. This 300 sq ft accommodation includes a separate bedroom and kitchen with a dining table, air conditioning, free WiFi, and on-site parking, accommodating up to two guests and two pets for an additional fee.
This Highland Park apartment rental is ideally situated in the Rivinia Business District, offering easy access to Highland Park's shops and restaurants. The ground-floor unit, accessible via one flight of stairs, features a fully equipped kitchen, a 55" Samsung Smart TV with Xbox One, in-building laundry, and parking; it comfortably sleeps two guests.
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.
10 1 review
Highland Park, IL
07/02 – 07/09
$649/nighttotal: $4543 (7 )
Northbrook Fhs Rental
1 2
apartment , Northbrook
This renovated apartment is located in a quiet suburb of Chicago, just 22 minutes from O’Hare Airport and 25 minutes from downtown Chicago. The apartment is conveniently located near local shops, restaurants, and parks, making it a perfect base for exploring the area. This 3-bedroom, 2-bathroom unit can comfortably accommodate up to 12 guests. The apartment offers a range of amenities including a fully equipped kitchen, a garden, parking, and a variety of entertainment options, including an air hockey table, a pinball machine, and a game console.
9.8 38 reviews
Highland Park, IL
06/28 – 07/05
$156/nighttotal: $1092 (7 )
The Hummingbird | Center Of Downtown Libertyville
1 2
apartment , Libertyville
This 375-square-foot studio apartment is located in Historic Downtown Libertyville, Illinois, steps from the Metra station and numerous restaurants and shops. The unit features a kitchen with Smeg appliances, accommodates two guests, and offers amenities including air conditioning, parking, and internet access; nearby attractions include the popular Libertyville bar and restaurant in the shared courtyard.
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.
9.3 3 reviews
Highland Park, IL
06/28 – 07/05
$314/nighttotal: $2198 (7 )
Cozy 3 Bedroom In Dt Libertyville Near Naval Base!
3 2
apartment , Libertyville
This 3-bedroom, 1-bathroom Libertyville house is a 5-minute walk from downtown Libertyville shops and restaurants, 8 miles from the Naval Base, and offers easy access to Six Flags and Lake Michigan beaches. This pet-friendly rental accommodates up to 9 guests with a King bed, Queen bed, Twin XL over Queen bunk, and a Queen pull-out couch, featuring a wood-burning fireplace, spacious backyard, fully equipped kitchen, high-speed internet, and ROKU TVs.
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.
Highland Park, IL
07/02 – 07/09
$190/nighttotal: $1330 (7 )
Studio Flat ∙ 1 Bedroom ∙ 2 Guests
1 2
studio , Glenview
This Glenview studio apartment is conveniently located in The Glen business district, near Northwestern University and a Metra station providing easy access to downtown Chicago. The 1-bedroom unit sleeps 2 guests and features a fully equipped kitchen, complimentary breakfast (Monday-Wednesday), an indoor pool, fitness center, and free parking; nearby attractions include the Kohl Children's Museum and the Illinois Holocaust Museum, both within 5 miles.
9.8 45 reviews
Highland Park, IL
08/02 – 08/04
$785/nighttotal: $1570 (2 )
6 Kings | Ping-pong | Gazebo!
1 2
apartment , Northbrook
This Northbrook apartment rental boasts a prime location near the intersection of I-294 and I-94, providing easy access to North Shore beaches, Chicago attractions, Wood Oaks Green Park (0.5 miles), and shopping destinations like Northbrook Court (2.5 miles). Sleeping 16 guests comfortably in 5 bedrooms and 3 bathrooms, this spacious residence features 6 king beds, 7 couches, multiple smart TVs with streaming services, a ping pong table, a large private backyard with a gazebo and fire pit, and parking for up to 6 cars.
Highland Park, IL
06/28 – 07/05
$258/nighttotal: $1806 (7 )
Home With Garage In Dt Libertyville Near Naval Base
2 2
house , Libertyville
This Libertyville house is conveniently located near Naval Station Great Lakes (7.9 miles) and Six Flags Great America (7.1 miles), offering easy access to Chicagoland attractions. This 890-square-foot home features two bedrooms, one bathroom, and sleeps up to 11 guests, including amenities such as free Wi-Fi, a fully equipped kitchen, and in-unit laundry.
9.8 24 reviews
Highland Park, IL
06/28 – 07/05
$288/nighttotal: $2016 (7 )
Great For Families Dt Libertyville Near Naval Base
3 2
apartment , Libertyville
This Libertyville apartment rental is conveniently located within walking distance of downtown Libertyville, offering easy access to the Metra train station and situated 8 miles from the Great Lakes Naval Base. This three-bedroom, two-bathroom unit sleeps eight guests comfortably and features a fully equipped kitchen, keyless entry, Roku TV with YouTube TV, a workspace with a printer, and a private garden; nearby attractions include the Bess Bower Dunn Museum and Independence Grove Forest Preserve.
Best Highland Park, IL vacation rentals with parking
Highland Park, IL
06/28 – 07/05
$335/nighttotal: $2345 (7 )
Stylish Retreat In Dt Libertyville Near Naval Base
3 2
apartment , Libertyville
This 3-bedroom, 1-bathroom apartment offers prime downtown Libertyville lodging, situated a 5-minute walk from MainStreet Libertyville's shops and restaurants, a 5-minute drive from Lambs Farm, and a 10-minute walk from the Libertyville Train Station. This family-friendly rental accommodates up to 9 guests and features on-site parking, a full kitchen with a dishwasher and microwave, air conditioning, an in-unit washer and dryer, and an outdoor space with a fire pit and barbecue.
10 3 reviews
Highland Park, IL
06/28 – 07/05
$269/nighttotal: $1883 (7 )
Home W/ Garage In Dt Libertyville Near Naval Base!
2 2
apartment , Libertyville
This charming cottage is conveniently located in Libertyville, just one hour north of Chicago and one hour south of Milwaukee, making it an ideal base for exploring the area. The town's vibrant downtown area offers a variety of restaurants, shops, and fun events for guests to enjoy. The cozy cabin has two bedrooms and one bathroom, comfortably accommodating up to six guests. The cottage includes modern amenities such as keyless entry, fast WiFi, a Roku TV with streaming services, and a fully equipped kitchen with a Keurig coffee maker.
10 21 reviews
Highland Park, IL
08/28 – 08/30
$811/nighttotal: $1622 (2 )
"Hope Of Evanston" 180°view, 2bdr +2bath Urban Luxury
2 2
apartment , Evanston
This Evanston apartment rental is conveniently located 1.3 miles from Lake Michigan and Northwestern University, a short walk from the Davis Metra Station. The two-bedroom, two-bathroom unit sleeps five, features a private balcony, in-unit fireplace, fully equipped kitchen with microwave and dishwasher, and access to a building swimming pool and fitness center.
10 1 review
Highland Park, IL
08/15 – 09/15
$215/nighttotal: $6665 (31 )
Modern 2-bedroom House With Free Parking And Convenient Location,
2 2
apartment , Skokie
This Skokie condo offers proximity to Old Orchard Mall, dining, entertainment, and public transit, with easy access to downtown Chicago. This rental features two bedrooms, a sofa bed, sleeping capacity for six, a fully equipped kitchen, complimentary toiletries, and parking for two vehicles.
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?
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?
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.
10 43 reviews
Highland Park, IL
08/28 – 08/30
$904/nighttotal: $1808 (2 )
"Unity Of Evanston" 3 Bdr+2ba Modernluxe High Rise
3 2
apartment , Evanston
This Evanston apartment is conveniently located just over a mile from Northwestern University and Lake Michigan, making it a great choice for travelers wanting to explore the area. Guests consistently rate the apartment excellent, highlighting its comfortable and well-maintained accommodations. This 3-bedroom unit offers 1400 square feet of space, comfortably accommodating up to 7 guests. Enjoy a range of amenities including a swimming pool, fitness center, and a private balcony, perfect for relaxing after a day of exploring Evanston.
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.
This Libertyville vacation home is located within 2-3 miles of Advocate Condell Medical Center, Lambs Farm, and MainStreet Libertyville, offering easy access to local attractions. This 2700-square-foot house features three bedrooms, three bathrooms, and can comfortably accommodate eight guests, boasting amenities such as a fully equipped kitchen, in-house laundry, and an on-site fitness center.
Highland Park, IL
06/28 – 07/05
$1535/nighttotal: $10745 (7 )
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.
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.
9.8 202 reviews
Highland Park, IL
08/28 – 08/30
$504/nighttotal: $1008 (2 )
Lovely Studio Near The Beach! (And Heated Floors!)
1 2
apartment , Highland Park
This studio apartment is located in Highland Park, within easy walking distance of downtown Highland Park, Highwood, and the beach, making it a great base for exploring the area. It has received excellent user ratings for its location, cleanliness, and overall experience. The studio has a separate sleeping area, living area, and dining nook, comfortably accommodating up to three guests. It includes a fully equipped kitchen, a cozy living space, a comfortable bed, and thoughtful amenities like coffee, a French press, a milk frother, and a variety of books and games.
9.6 10 reviews
Highland Park, IL
06/28 – 07/05
$286/nighttotal: $2002 (7 )
Downtown Libertyville Duplex Near Naval Base!
3 2
apartment , Libertyville
This modern apartment is located in downtown Libertyville, just a short walk from the Village Square and its shops and restaurants. This central location offers easy access to the area's attractions, including the Marriott and Citadel Theatres. This three-bedroom dwelling comfortably accommodates up to eight guests with king and queen beds in each bedroom and a pull-out sofa in the living room. The apartment features a fully equipped kitchen, a washer and dryer, a Roku TV, free Wi-Fi, and a Keurig coffee maker.
8.7 12 reviews
Highland Park, IL
06/28 – 07/05
$267/nighttotal: $1869 (7 )
Downtown Libertyville Duplex Near Naval Base!
3 2
apartment , Libertyville
This three-bedroom apartment is situated in downtown Libertyville, a short 15-minute drive from the Great Lakes Naval Base. The apartment features a fully equipped kitchen, washer and dryer, and a Roku TV, comfortably accommodating up to eight guests.
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.
