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Best Vacation rentals and Airbnb offers in Highland Park, IL
8.8 39 reviews
Highland Park, IL
08/15 – 09/15
$154/nighttotal: $4774 (31 )
Comfortable 2 Bedroom House Near Great Lakes Navy Base Ideal For Families
2 2
apartment , North Chicago
This 2-bedroom apartment in North Chicago offers convenient access to Great Lakes Navy Base, Rosalind Franklin University, Six Flags Great America (less than 5 miles away), and American Place Casino. This private rental accommodates up to 6 guests and features a full kitchen, a patio with a grill, and a living room with a 55-inch TV, with each bedroom also equipped with a TV.
Highland Park, IL
08/15 – 09/15
$109/nighttotal: $3379 (31 )
Charming 1-bedroom Apartment With Wifi, Ac In Glenview, Great School District
1 2
apartment , Glenview
This Glenview apartment rental is ideally situated in a great school district, offering convenient access to attractions like the Baha'i House of Worship and Allstate Arena, as well as shopping at Woodfield and Golf Mill Shopping Centers. This two-bedroom, one-bathroom unit sleeps four guests and includes Wi-Fi, air conditioning, laundry facilities, and amenities such as hair dryers and ironing boards.
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.
This studio apartment is conveniently located in Highland Park's Rivinia Business District, just a short walk from the lakefront, the Chicago Botanic Gardens, and the Metra station. It boasts excellent ratings for location, cleanliness, and overall user experience. This quiet, private apartment is perfect for two guests and features a fully equipped kitchen, a comfortable living space, and a modern bathroom. Guests can enjoy free amenities such as parking, laundry, and a fitness center, making it an ideal choice for travelers seeking a comfortable and convenient stay.
Highland Park, IL
07/11 – 07/14
$632/nighttotal: $1896 (3 )
Modern 4bd 2ba Home Near Downtown Metra
4 2
house , Highland Park
This modern 4-bedroom, 2-bathroom house in Highland Park offers convenient access to downtown Metra for Chicago travel and is 1.2 miles from Openlands Lakeshore Beach. This 130 square feet home accommodates up to 12 guests with a fully equipped kitchen, air conditioning, and complimentary Wi-Fi, located 16-24 miles from Chicago attractions and 18 miles from Chicago O'Hare International Airport.
Highland Park, IL
08/15 – 09/15
$371/nighttotal: $11501 (31 )
Cozy 4bd 2ba Home Near Downtown / Metra
1 2
apartment , Highland Park
This 4-bedroom, 2-bathroom rental residence is located in Highland Park, just blocks from downtown Highwood and Highland Park, and 0.2 miles from the Metra station. This pet-friendly apartment offers a capacity of 8 guests with air conditioning, a kitchen, and internet, featuring an open-concept layout and brand-new flooring.
Highland Park, IL
08/15 – 09/15
$264/nighttotal: $8184 (31 )
New! Bright Modern 3bed 2.5bath Evanston Home W/parking By Allset Turnover
3 2
apartment , Evanston
This two-story Evanston house is located in North Evanston, offering proximity to Lake Michigan, Grosse Point Lighthouse, and convenient access to Central corridor shops and restaurants, with the Metra and Purple Line a short drive away. This 1600 square foot residence accommodates up to 9 guests, featuring 3 bedrooms, 2 bathrooms, a chef's kitchen with a fridge and microwave, air conditioning, internet, and a private backyard.
9.0 2 reviews
Highland Park, IL
08/15 – 09/15
$276/nighttotal: $8556 (31 )
Northbrook Rental
1 2
apartment , Northbrook
This Northbrook apartment is conveniently located just 22 minutes from O'Hare Airport and 25 minutes from downtown Chicago, making it an ideal base for exploring the city and surrounding areas. The suburban setting offers a peaceful retreat from the hustle and bustle of urban life. This spacious 3-bedroom, 2-bathroom dwelling comfortably accommodates up to 6 guests. The apartment is equipped with modern amenities, including a fully equipped kitchen, high-speed internet, multiple LCD TVs, and a variety of entertainment options, ensuring a comfortable and enjoyable stay for families and groups alike.
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.
9.4 6 reviews
Highland Park, IL
08/15 – 09/15
$212/nighttotal: $6572 (31 )
Downtown Libertyville Apt Near Naval Base
2 2
apartment , Libertyville
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.
9.4 14 reviews
Highland Park, IL
08/15 – 09/15
$230/nighttotal: $7130 (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 near the Great Lakes Naval Base (a 20-minute drive). The two-bedroom, one-bathroom unit sleeps up to seven guests comfortably, featuring a fully equipped kitchen with a dishwasher, high-speed internet, YouTube TV, and parking for two cars.
10 1 review
Highland Park, IL
07/11 – 07/14
$1581/nighttotal: $4743 (3 )
1 Mi To Metra: Estate W/ Theater, Game Room & More
4 2
apartment , Northbrook
This 9,500 sq ft luxury house in Northbrook is located 1 mile from the Metra station for Chicago access, close to shopping and dining, and a short drive to the Botanic Garden. This spacious vacation rental accommodates 8 guests with 4 bedrooms, 7 bathrooms, a home theater, game room, home gym, and extensive outdoor entertainment including a backyard with a trampoline and fire pit.
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.
9.6 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.
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.
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.
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
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.
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.
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.
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?
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.
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.
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.
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.
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.
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.