Find short term rentals in Highland Park, IL at the best prices
31 available short term rental offers
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Best Short term and Weekly rentals in Highland Park, IL
Highland Park, IL
15/08 – 15/09
$281/nighttotal: $8711 (31 )
Quaint And Cozy 2 Bedroom Apt Near Highwood Train!
1 2
apartment , Highwood
This Highwood apartment, situated near Highwood train station, provides easy access to Chicago's city centre via a 35-minute express train journey and is also close to Six Flags Great America, Great Lakes Naval Base, and Lake Michigan beaches. The two-bedroom, one-bathroom flat sleeps seven guests, features a fully equipped kitchen with dishwasher, parking for two cars, air conditioning, high-speed internet, and YouTube TV, making it ideal for families or groups visiting the area.
10 1 review
Highland Park, IL
02/07 – 09/07
$908/nighttotal: $6356 (7 )
Northbrook Fhs Rental
1 2
apartment , Northbrook
This spacious apartment is conveniently located in a residential area of Chicago, just 22 minutes from O’Hare Airport and 25 minutes from the city centre. The apartment is ideal for families or groups of up to 12 guests, with three bedrooms and two bathrooms. The apartment is well-equipped with everything you need for a comfortable stay, including a fully-fitted kitchen, high-speed internet, and a range of entertainment options. There is also a garden and parking for one car.
9.9 42 reviews
Highland Park, IL
28/08 – 30/08
$1282/nighttotal: $2564 (2 )
North Shore Blue-door Bungalow
3 2
apartment , Highland Park
This charming bungalow is located in Highland Park, just under 1.6 kilometres from Highland Park Hospital and Uptown Highland Park, offering easy access to amenities, green spaces and a peaceful setting across from Sunset Park. The house has three bedrooms and one bathroom, comfortably accommodating up to four guests. It features a fully equipped kitchen, air conditioning, parking, internet access, and a welcoming atmosphere for families and pets.
8.7 12 reviews
Highland Park, IL
28/06 – 05/07
$374/nighttotal: $2618 (7 )
Downtown Libertyville Duplex Near Naval Base!
3 2
apartment , Libertyville
This modern three-bedroom apartment is situated in the heart of Libertyville, just 13 kilometres from the Naval Base and within a one-hour drive of both Chicago and Milwaukee. The apartment comfortably sleeps eight guests and features a fully equipped kitchen with a Keurig coffee maker, a crock pot, a washing machine and dryer, and free Wi-Fi.
10 6 reviews
Highland Park, IL
02/07 – 09/07
$1030/nighttotal: $7210 (7 )
The Pleasant Hill Cottage North Shore Enchantment
3 2
apartment , Highwood
This Highwood cottage, a short distance from Lake Michigan beaches, Ravinia Festival, and the Chicago Botanic Garden, offers easy access to Chicago by train. The three-bedroom, two-bathroom property sleeps ten guests and includes a fully equipped kitchen, garden, fitness centre, parking, and numerous family-friendly amenities such as a travel crib and highchair.
9.7 6 reviews
Highland Park, IL
02/08 – 04/08
$184/nighttotal: $368 (2 )
Private 3rd Floor Steps From Lake Michigan
1 2
apartment , Highland Park
This private third-floor flat in Highland Park offers excellent access to Lake Michigan, located within 500 meters, and the dining and shopping areas of Highland Park and Highwood, with direct Metra train access to central Chicago. This accommodation for two guests features a kitchenette with a fridge and microwave, air conditioning, a garden, and a European-style shower, with optional paddleboarding lessons available on Lake Michigan.
9.9 161 reviews
Highland Park, IL
02/07 – 09/07
$264/nighttotal: $1848 (7 )
Charming Space W/ Use Of Deck And Yard
1 2
B&B , Highland Park
This self-contained studio apartment is located in the basement of a charming house in Highland Park, just a 1.6km walk from downtown Highwood and its Metra train station. Guests have rated this property highly for its location, cleanliness, and overall experience. The studio is ideal for two guests and offers a private and comfortable space with a fully equipped kitchen and bathroom. Guests can enjoy access to a private yard and decks, a fitness area with a treadmill and punching bag, and the friendly hosts live upstairs and are available for any assistance needed during the stay.
9.6 24 reviews
Highland Park, IL
02/08 – 04/08
$191/nighttotal: $382 (2 )
An Spacious Quiet Bedroom In A Charming House
1 2
apartment , Northbrook
This Northbrook bed and breakfast is located just under a kilometre from the town centre and the Metra station, providing easy access to both Northbrook's amenities and Chicago. The self-catering property offers a fully equipped kitchen, a private bathroom, and a spacious backyard, ideal for a relaxing stay in the area.
9.8 193 reviews
Highland Park, IL
02/08 – 04/08
$874/nighttotal: $1748 (2 )
Chicago's Hidden Treasure, "Evanston, Il"
2 2
apartment , Evanston
This two-bedroom apartment is located in downtown Evanston, just 800 metres from Northwestern University and a short walk from restaurants, cafes, and shops. The apartment has received excellent ratings for location, cleanliness, and overall experience. The 92 square metre apartment comfortably sleeps five guests and has a modern design with granite countertops, 9-foot ceilings, and designer flooring. Guests can enjoy a range of amenities, including a swimming pool, fitness centre, garden, and a spa.
9.8 139 reviews
Highland Park, IL
28/08 – 30/08
$2094/nighttotal: $4188 (2 )
Rejuvenate And Relax In The North Shore
1 2
apartment , Highland Park
This four-bedroom apartment in Highland Park is conveniently located just a short distance from Lake Michigan, the Chicago Botanical Garden, and Ravinia Festival, offering easy access to these attractions. It has received excellent ratings for its location, cleanliness, and user experience. The property comfortably accommodates up to 12 guests and features a large yard with outdoor furniture and a propane BBQ grill. Guests can enjoy amenities such as air hockey, darts, and board games, as well as a fully equipped kitchen with a fridge, microwave, dishwasher, and access to the entire home, including the garage.
Highland Park, IL
28/06 – 05/07
$284/nighttotal: $1988 (7 )
Cozy Apartment In Dt Libertyville, Near Naval Base
1 2
apartment , Libertyville
This Libertyville flat is centrally located, 13 kilometres south of the Great Lakes Naval Base and equidistant from Chicago and Milwaukee, with easy access to Six Flags, Lake Michigan beaches, forest preserves, and the Chain of Lakes, all within walking distance of downtown Libertyville's restaurants and shops. This newly designed 2nd-floor apartment accommodates two guests and features a dedicated living area, a fully equipped kitchen with a fridge, microwave oven, and dishwasher, air conditioning, parking, and a King Bed, with pets welcome for a nightly fee.
9.9 16 reviews
Highland Park, IL
28/08 – 30/08
$176/nighttotal: $352 (2 )
Studio 6 Vernon Hills Relax Queen Bed Nsmk Kitchen
1 2
apartment , Vernon Hills
This Mettawa flat is situated 27 kilometres from Chicago O'Hare International Airport and within 20 kilometres of Six Flags Great America. This one-bedroom flat, covering 28 square metres, accommodates two guests with a queen bed and sofa bed, offering a fully equipped kitchen, air conditioning, and on-site private parking.
Best family friendly Highland Park, IL Short term rentals
Among the 31 accommodations in Highland Park, IL, here are the 4 best family friendly rentals
Highland Park, IL
28/06 – 05/07
$835/nighttotal: $5845 (7 )
Dt Libertyville Home W/ 2 Fireplaces By Navy Base!
1 2
apartment , Libertyville
This Libertyville flat is situated a 10 to 15-minute walk from Downtown Libertyville and is 12.8 kilometres (a 15-minute drive) from the Great Lakes Naval Base, offering a special offer for Navy graduate families including a complimentary pizza night. This spacious residence accommodates up to 12 guests across five bedrooms and a sleep sofa, featuring two separate living areas with fireplaces, a modern kitchen with granite countertops and stainless steel appliances, two bathrooms, built-in workstations, and a large, fenced garden with a grill area, all within easy reach of local shops, restaurants, Six Flags, Lake Michigan beaches, and forest preserves.
Highland Park, IL
28/06 – 05/07
$468/nighttotal: $3276 (7 )
Stylish Retreat In Dt Libertyville Near Naval Base
3 2
apartment , Libertyville
This second-floor flat in Libertyville is located centrally, 160 kilometres north of Chicago and 160 kilometres south of Milwaukee, approximately 24 kilometres from the Great Lakes Naval Base. Accommodating up to nine guests across three bedrooms, this property offers a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, Wi-Fi, and parking, with nearby attractions including Six Flags, Lake Michigan beaches, forest preserves, and the Bess Bower Dunn Museum of Lake County.
9.6 5 reviews
Highland Park, IL
15/08 – 15/09
$544/nighttotal: $16864 (31 )
Entire Home, Close To Highway, Serene Neighborhood
1 2
apartment , Northbrook
This three-bedroom flat in Northbrook offers excellent access to the greater Chicagoland area, situated just 5 kilometres from the M94 motorway and a 21-minute drive from downtown Wilmette and Winnetka. This family-friendly residence accommodates up to six guests and features a private office, two rooms with Roku TVs, a spacious garden, ample parking, and in-home laundry facilities.
10 1 review
Highland Park, IL
28/06 – 05/07
$384/nighttotal: $2688 (7 )
Downtown Libertyville Duplex Near Naval Base
3 2
apartment , Libertyville
This Libertyville duplex, near the Naval Training Centre Great Lakes (13km), offers easy access to Six Flags Great America (12km), Ravinia Festival (23km), and the Chicago Botanic Garden (26km). This three-bedroom apartment, boasting 173 square metres of floor space, comfortably sleeps fourteen guests and includes a fully equipped kitchen, garden, private parking, and complimentary Wi-Fi.
Best Highland Park, IL lodging with a kitchen
10 1 review
Highland Park, IL
02/08 – 04/08
$1039/nighttotal: $2078 (2 )
Parisian Inspired Escape - Close To Town & Nu
2 2
apartment , Evanston
This two-bedroom flat is located in Evanston's Church & Dodge district, 800 metres from Downtown Evanston and less than 1.6 kilometres from Northwestern University. This family-friendly property offers a gourmet kitchen, a lower-level family room with a movie screen, an office space, a sunny patio, and is close to Lake Michigan for water activities and Michigan Avenue for shopping.
9.9 109 reviews
Highland Park, IL
28/08 – 30/08
$646/nighttotal: $1292 (2 )
Modern Retreat Near Ravinia & Botanic Gardens
1 2
apartment , Highland Park
This Highland Park bed and breakfast is located just a short distance from the Ravinia Festival and the Chicago Botanic Garden, providing easy access to these popular attractions. The self-catering guest house offers a private bedroom, bathroom, and living room, perfect for couples or solo travellers looking for a comfortable and spacious retreat.
9.4 6 reviews
Highland Park, IL
15/08 – 15/09
$297/nighttotal: $9207 (31 )
Downtown Libertyville Apt Near Naval Base
2 2
apartment , Libertyville
This two-bedroom apartment is conveniently situated in the heart of Libertyville, just a short walk from the town's main street and within easy reach of restaurants, shops and events. It's approximately 80 kilometres north of Chicago and 160 kilometres south of Milwaukee, making it an ideal base for exploring the area. This property has received excellent guest reviews, highlighting its comfortable and well-equipped nature. The apartment offers a spacious living area, perfect for families or groups of up to six guests. Amenities include a fully equipped kitchen, air conditioning, free high-speed internet, parking and a convenient location near attractions such as Six Flags Great America, Lambs Farm, the Lake County Fairgrounds and the Chain of Lakes.
Frequently Asked Questions about short term rentals in Highland Park, IL
What are the best short term rentals in Highland Park, IL?
Best Highland Park, IL lodging with laundry available
10 33 reviews
Highland Park, IL
02/08 – 04/08
$440/nighttotal: $880 (2 )
4 Bedroom, 2 Full Bath. Centrally Located. Near O'hare Airport And Attractions
4 2
apartment , Glenview
This Glenview holiday home is situated 1.8km from Golf Mill Shopping Centre and within 4.8km of Glenbrook Hospital and The Glen Club. The 167 square metre property boasts four bedrooms, two bathrooms, sleeps six guests, and includes a fully equipped kitchen with appliances such as a fridge, microwave, dishwasher, coffee maker and kettle, plus in-unit laundry facilities.
This Libertyville holiday home is situated within 3-5km of Advocate Condell Medical Center, Lambs Farm, and MainStreet Libertyville, offering easy access to local attractions. The 251 square metre property boasts three bedrooms, three bathrooms, and sleeps eight, including amenities such as a fully equipped kitchen, fitness centre, and in-house laundry facilities.
Highland Park, IL
02/08 – 04/08
$300/nighttotal: $600 (2 )
Condo ∙ 1 Bedroom ∙ 3 Guests
1 2
apartment , Lincolnshire
This apartment is ideally located in Lincolnshire's business district, just a short distance from suburban Chicago destinations like Vernon Hills, Deerfield, and Buffalo Grove. It is also within easy reach of Abbott, Grainger, Stevenson HS, Great Lakes Naval Base, AON & Alight. The apartment has one bedroom and one bathroom, comfortably accommodating up to three guests. It offers a range of amenities, including a swimming pool, fitness centre, free shuttle service, complimentary breakfast, and evening receptions.
8.5 21 reviews
Highland Park, IL
28/06 – 05/07
$221/nighttotal: $1547 (7 )
Green #2
1 2
B&B , Glenview
This two-bedroom flat is situated in Northbrook, just a 15-minute drive from O'Hare International Airport and the Rosemont Convention Center, making it a convenient base for exploring Glenview and the surrounding area. It has consistently received excellent ratings for its location, cleanliness, and overall experience, ensuring a comfortable and enjoyable stay. The apartment comfortably sleeps five guests and boasts a well-equipped kitchen, air conditioning, and parking, ensuring a comfortable and convenient stay. It also offers internet access, making it easy to stay connected during your trip.
Best Highland Park, IL lodging with air conditioning
9.0 7 reviews
Highland Park, IL
30/07 – 02/08
$1506/nighttotal: $4518 (3 )
6 Kings Ping-pong Gazebo!
5 2
apartment , Northbrook
This Northbrook holiday home provides easy access to Lake Michigan and the Edward L. Ryerson Conservation Area, conveniently located for exploring both the North Shore beaches and Chicago's city centre. This five-bedroom property, boasting 236 square metres of floor space, comfortably accommodates sixteen guests with six king-size beds, four bathrooms, multiple smart TVs (including Disney+ and Hulu), a ping pong table, ample parking, and a large yard with a gazebo.
9.9 15 reviews
Highland Park, IL
28/08 – 30/08
$1650/nighttotal: $3300 (2 )
Bohemian Bungalow - Highwood, Navy Base, & Ravinia
3 2
apartment , Highland Park
This Highland Park flat is located between the districts of Highland Park and Highwood, offering convenient access to dining, music venues, and shops, with the Metra train station just a short walk away for commutes to Chicago and the Naval Station, and close to the Ravinia Festival, the beach, and a cycle path. This three-bedroom flat sleeps five guests and features a kitchen with a retro fridge, a dedicated office space, a small fenced garden with a firepit, and a SmartTV, providing a comfortable stay with amenities for both work and leisure.
Highland Park, IL
15/08 – 15/09
$90/nighttotal: $2790 (31 )
Downtown Highwood
2 2
apartment , Highwood
This charming bed and breakfast is located in Highwood, just a short walk from restaurants, bars, and live music venues, and a 10-minute train ride from Chicago. The area is lively and offers easy access to both the excitement of the city and the peacefulness of the suburbs. The guesthouse has two bedrooms and one bathroom, comfortably accommodating up to four guests. It features a shared kitchen, a private bathroom for guests, and secure parking for two cars.
10 103 reviews
Highland Park, IL
28/08 – 30/08
$1600/nighttotal: $3200 (2 )
Re-imagined 1880s Cottage By Highwood, Metra, Lake
2 2
apartment , Highland Park
This charming cottage is situated in a peaceful residential neighbourhood in Highland Park, just 40 kilometres north of Chicago, with easy access to the North Shore bike path, the Metra train station, and the Highwood restaurant district. It has received excellent ratings for location, cleanliness and user experience. The cottage offers two bedrooms and one bathroom, comfortably accommodating up to six guests. Enjoy a range of amenities including a fully equipped kitchen, air conditioning, a jacuzzi, a garden, and a wrap-around porch.