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
Highland Park, IL
08/02 – 08/04
$235/nighttotal: $470 (2 )
Condo ∙ 1 Bedroom ∙ 2 Guests
1 2
apartment , Glenview
This Glenview apartment rental is conveniently located in The Glen business district, near the Metra station providing easy access to downtown Chicago, Northwestern University, and major corporations like Allstate and Kraft. The one-bedroom, one-bathroom unit sleeps two guests and offers amenities including a fully equipped kitchen, complimentary breakfast (Monday-Wednesday), an indoor heated pool, a 24-hour fitness center, and free on-site parking.
This two-bedroom apartment is conveniently located in Libertyville, within walking distance of downtown and close to MainStreet Libertyville and Cuneo Mansion and Gardens. Guests have consistently rated this rental as "very good" for its location and amenities. This rental comfortably accommodates up to six guests and offers a fully equipped kitchen with a refrigerator and microwave. The apartment also includes free high-speed internet, air conditioning, parking, and a basement for extra storage.
Highland Park, IL
08/15 – 09/15
$197/nighttotal: $6107 (31 )
56 M² Apartment ∙ 1 Bedroom ∙ 2 Guests
1 2
apartment , Evanston
This one-bedroom furnished apartment is located in Evanston, 12 miles north of downtown Chicago and adjacent to Northwestern University. This 600-square-foot unit accommodates up to two guests and includes a fully equipped kitchen, superior quality linens, a smart TV, and on-site laundry, parking, and pet-friendly options.
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.
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
$201/nighttotal: $6231 (31 )
Quaint And Cozy 2 Bedroom Apt Near Highwood Train!
1 2
apartment , Highwood
This Highwood apartment rental is conveniently located near the Highwood train station, providing easy access to downtown Chicago via a 35-minute express train ride. The two-bedroom, one-bathroom unit sleeps seven guests, features a fully equipped kitchen with a dishwasher, in-unit laundry, a workspace, YouTube TV, and parking for two cars, all within easy reach of Six Flags Great America, the Great Lakes Naval Training Center, Lake Michigan beaches, and local forest preserves.
9.6 8 reviews
Highland Park, IL
08/15 – 09/15
$258/nighttotal: $7998 (31 )
Lovely Duplex In Dt Libertyville Near Naval Base!
3 2
apartment , Libertyville
This Libertyville apartment is located in downtown Libertyville, a trendy town with several restaurants and shops, about an hour north of Chicago and an hour south of Milwaukee. It has an excellent user rating, making it a popular choice for travelers. This 3-bedroom, 1-bathroom rental can accommodate up to 8 guests. The apartment includes a fully equipped kitchen, a garden, parking, and a variety of amenities, making it a comfortable and convenient place to stay.
10 36 reviews
Highland Park, IL
08/28 – 08/30
$1034/nighttotal: $2068 (2 )
North Shore - Home Away From Home
1 2
apartment , Highland Park
This Highland Park home is just a short distance from the downtown area, offering easy access to shops, restaurants, and the scenic lakefront. The quiet neighborhood provides a peaceful retreat, perfect for families looking to relax and enjoy their time together. This 4-bedroom, 2-bathroom home comfortably accommodates up to 6 guests. The home offers amenities like a fully equipped kitchen, air conditioning, a garden, and parking, along with family-friendly features like a large family room with foosball, video games, and a toy closet.
8.8 16 reviews
Highland Park, IL
08/15 – 09/15
$202/nighttotal: $6262 (31 )
Entire Beautiful Grove Home
3 2
apartment , North Chicago
This fully furnished three-bedroom home is conveniently located in North Chicago, 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 comfortable apartment can accommodate up to six guests and offers a cozy family room with a fireplace. The apartment comes equipped with a kitchen that includes a fridge, freezer, microwave oven, and dishwasher, as well as air conditioning, a garden, and parking.
9.9 12 reviews
Highland Park, IL
08/02 – 08/04
$125/nighttotal: $250 (2 )
1 King Bed | Non-smoking, Kitchen
1 2
apartment , Vernon Hills
This Mettawa rental unit is located approximately 16 miles from Chicago O'Hare International Airport and 12 miles from Six Flags Great America. This 300 sq ft one-bedroom, one-bathroom condo accommodates two guests and features a fully equipped kitchen, a king bed, air conditioning, free WiFi, and on-site parking.
9.8 18 reviews
Highland Park, IL
08/15 – 09/15
$299/nighttotal: $9269 (31 )
Home W/ Porch In Dt Libertyville Near Naval Base
3 2
apartment , Libertyville
This Libertyville vacation home is conveniently located less than 1.2 miles from MainStreet Libertyville, offering easy access to shopping, dining, and attractions like Lambs Farm and Pine Meadow Golf Club (within 3 miles). This three-bedroom, two-bathroom house comfortably sleeps 10 guests and features a fully equipped kitchen, free Wi-Fi, a garden, parking, and is pet-friendly.
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.
9.9 168 reviews
Highland Park, IL
08/28 – 08/30
$644/nighttotal: $1288 (2 )
Cozy 2-bedroom Cottage Near Downtown Highland Park
1 2
apartment , Highland Park
This apartment is located just a few blocks from the downtown areas of Highland Park and Highwood, offering easy access to restaurants, bars, and shops. The apartment has received excellent ratings for cleanliness, location, and overall user experience. The apartment features two bedrooms with comfortable queen-size beds and a fully remodeled bathroom with a rain shower head. The living room and dining room provide ample space for relaxing and gathering, and the kitchenette includes a microwave, mini refrigerator, coffee maker, and toaster.
Highland Park, IL
08/28 – 08/30
$857/nighttotal: $1714 (2 )
Parisian Inspired Escape - Close To Town & Nu
2 2
apartment , Evanston
This 2-bedroom rental unit is located in Evanston's Church & Dodge neighborhood, a half-mile from Downtown Evanston and less than a mile from Northwestern University. This family-friendly apartment accommodates up to six guests and features a gourmet kitchen, a family room with a movie screen, an office, a patio, and is close to the beach, Lake Michigan, and various water and cycling activities.
Highland Park, IL
08/28 – 08/30
$152/nighttotal: $304 (2 )
Studio Flat ∙ 1 Bedroom ∙ 2 Guests
1 2
studio , Glenview
This Glenview studio condo is conveniently located near Gallery Park and Meadowhill Park, offering easy access to outdoor recreation. This one-bedroom unit, perfect for two guests, boasts a fully equipped kitchen with a dishwasher, a comfortable living area with a flatscreen TV and premium cable, free Wi-Fi, on-site parking, and access to a seasonal indoor pool and 24-hour fitness center at the Staybridge Suites complex, including a daily breakfast buffet.
9.8 149 reviews
Highland Park, IL
08/28 – 08/30
$3106/nighttotal: $6212 (2 )
2-acre Highland Park Retreat With Heated Pool ~ 5*
1 2
apartment , Highland Park
This luxurious Highland Park apartment is located in a quiet neighborhood, just a short drive from the Ravinia Festival and Chicago Botanic Garden. The apartment has received excellent ratings for its cleanliness, location, and overall experience. This spacious rental has six bedrooms and can accommodate up to 15 guests. The apartment offers a heated pool, multiple living areas, a fully equipped kitchen, a basement entertainment zone with a gaming table, and a backyard perfect for outdoor activities.
Best Highland Park, IL vacation rentals with parking
Highland Park, IL
08/15 – 09/15
$294/nighttotal: $9114 (31 )
4br, 3ba, Home Evanston, Il, Near Northwestern Univ, Fully Furnished, Equipped
4 2
apartment , Evanston
This four-bedroom, three-bathroom Evanston rental is located one block from Lake Michigan in the desirable North Evanston neighborhood, offering easy access to the lakefront and proximity to downtown Evanston attractions. This spacious home features a large basement, a private garden, a terrace, a jacuzzi, and parking, comfortably accommodating five guests with a fully equipped kitchen including a fridge, microwave, and dishwasher; enjoy easy access to sporting events at Wrigley Field and Allstate Arena (though requiring travel).
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.
Highland Park, IL
08/15 – 09/15
$268/nighttotal: $8308 (31 )
Furnished Lake Forest 3br Townhome Monthly Housing Near Great Lakes
3 2
apartment , Lake Forest
This Lake Forest vacation rental is a 7-minute walk from Market Square and a 3-minute drive from Lake Michigan, offering easy access to the East Lake Forest train station. This 1400-square-foot house features 3 bedrooms, 2 bathrooms, a fully equipped kitchen with a dishwasher and microwave, in-unit laundry, and parking; it comfortably accommodates up to six guests and is near Conway Farms Golf Club and Six Flags Great America.
10 20 reviews
Highland Park, IL
08/28 – 08/30
$891/nighttotal: $1782 (2 )
"Faith Of Evanston" 180°view, 2bdr +2bath Urban Luxury
2 2
apartment , Evanston
This Evanston apartment rental is conveniently located 1.3 miles from both Lake Michigan and Northwestern University, offering easy access to public transportation via the Davis and Evanston Davis Street Metra stations. The two-bedroom, two-bathroom unit sleeps five guests and features a fully equipped kitchen, in-unit fireplace, private balcony, free WiFi, access to a swimming pool and fitness center, and parking.
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 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.
9.9 182 reviews
Highland Park, IL
08/28 – 08/30
$770/nighttotal: $1540 (2 )
"Serenity Of Evanston" 2 Bdr/2bath Modern-luxe Suite
2 2
apartment , Evanston
This Evanston apartment is located in downtown, a short walk from Northwestern University and a 15-minute train ride from Chicago. It has received excellent ratings for location, cleanliness, and overall user experience. The apartment has two bedrooms and two bathrooms, comfortably accommodating up to five guests. It features a modern design with granite countertops and designer flooring, along with amenities like a fitness center, swimming pool, and parking.
10 33 reviews
Highland Park, IL
08/28 – 08/30
$822/nighttotal: $1644 (2 )
"Bliss Of Evanston" 180°view, 2bdr +2bath Urbanlux
2 2
apartment , Evanston
This Evanston rental is located just 1.3 miles from Northwestern University and 1.3 miles from Lake Michigan, offering a peaceful setting near the river. The apartment has excellent user ratings, making it a popular choice for travelers. This 2-bedroom, 2-bathroom apartment offers 1250 square feet of space, comfortably accommodating up to 5 guests. Enjoy a range of amenities, including a swimming pool, fitness center, spa, and a private balcony, perfect for relaxing and enjoying your stay.
9.9 176 reviews
Highland Park, IL
08/28 – 08/30
$427/nighttotal: $854 (2 )
Executively Appointed Condo, W/resort Amenities, Ind Gar, Pool, Gym+ Biz Lounge
2 2
apartment , Evanston
This modern condo is located in downtown Evanston, just steps from Northwestern University and Loyola, with Kellogg School of Management a short distance away. The apartment receives excellent ratings for location, cleanliness, and overall user experience. The 1-bedroom, 1-bathroom apartment comfortably sleeps 4 guests. Enjoy resort-style amenities like a fitness center, swimming pool, and outdoor terrace, along with a fully equipped kitchen and high-speed internet.
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.
9.5 15 reviews
Highland Park, IL
08/02 – 08/04
$123/nighttotal: $246 (2 )
1 King Bed | Non-smoking, Kitchen, Shower
1 2
apartment , Vernon Hills
This apartment in Mettawa is 17 miles from Chicago O'Hare International Airport and 12 miles from Six Flags Great America. This 300 sq ft studio unit accommodates 2 guests and features air conditioning, a kitchen with a fridge and microwave, and on-site parking.
10 13 reviews
Highland Park, IL
08/28 – 08/30
$125/nighttotal: $250 (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.
Highland Park, IL
08/15 – 09/15
$162/nighttotal: $5022 (31 )
Stylish 1 Bedroom Apartment 2 Stops To Naval Base!
2 2
apartment , Highwood
This 670 sq ft, 2-bedroom, 1-bathroom apartment is located on the first floor in downtown Highwood, just a 5-minute walk to the train station and a 20-minute drive to the Great Lakes Naval Base. This pet-friendly unit accommodates up to 4 guests and features a fully equipped kitchen, high-speed internet, air conditioning, on-site parking, and offers complimentary pizza for Navy graduate families on Thursday evenings.
10 1 review
Highland Park, IL
08/15 – 09/15
$314/nighttotal: $9734 (31 )
Cozy 3 Bedroom In Dt Libertyville Near Naval Base!
1 2
apartment , Libertyville
This Libertyville apartment rental is a 5-minute walk from MainStreet Libertyville and a 5-minute drive from Lambs Farm. The four-bedroom, one-bathroom home features a fully equipped kitchen, in-unit laundry, free Wi-Fi, a fireplace, air conditioning, covered parking, and a private garden with barbecue facilities, comfortably accommodating families or groups.
