Choose the right place for you


  • 9+ Exceptional
  • 8+ Fabulous
  • 7+ Very Good


  • Less than 1 km
  • Less than 3 km
  • Less than 5 km

Vacation rental deals in Highland Park

We have selected the best vacation rentals in Highland Park. Save money with Bluepillow by comparing the best deals from major travel websites in Highland Park

  • Highland Park Oasis

    10 Exceptional (112)
    • 3 Guests · 1Bedroom
    Sunny second floor bedroom on quiet residential tree-lined street. The house is 1 mile from downtown Highland Park and 1/2 mile from Highwood. Great restaurants, coffee shops, library, shopping. The lake
  • Comfortable room in Northbrook

    10 Exceptional (46)
    • 2 Guests · 1Bedroom
    Great location if you are visiting one of the many corporate HQs in the northern suburbs. Less than 2 miles to the Metra train (to Chicago Union Station), and less than 30 minutes to O'Hare. This is
  • Private Room and Bath, all travelers welcome!!!

    10 Exceptional (90)
    • 2 Guests · 1Bedroom
    Very nice apartment with plenty of amenities. Near Ravinia and the Chicago Botanic Gardens. For business travelers very close to Walgreens Headquarters, Discover, Takada and many other corporate headquarters.
  • Home in a quiet neighborhood close to everything

    10 Exceptional (3)
    • 2 Guests · 1Bedroom
    Come to our sunny and modern home in a quiet neighborhood. Our home is 5 min away from Ravinia and Chicago Botanic Garden. Two blocks away from the bike path. 8 minutes from downtown Highland Park.
  • Perfect for Individual Travelers #1

    10 Exceptional (55)
    • 1 Guest · 1Bedroom
    Book a bed with us - the coolest low-rate room in town. With a tasteful interior, soft lighting and great attention to detail, this room creates just the right atmosphere. Decorated in neutral colors,
  • Courtyard Chicago Highland Park/Northbrook

    8.9 Fabulous (77)
    • Hotel
    This property is 11 minutes walk from the beach. This Highland Park, Illinois hotel features an indoor pool and rooms include free Wi-Fi and cable TV with HBO. Chicago Botanical Gardens are less than one

Save on Bed & Breakfast in Highland Park

Are you looking for an accommodation in Highland Park and do you want to save money? Choose from 10 Bed & Breakfasts in Highland Park

  • Hyatt Regency Deerfield

    8.1 Fabulous (844)
    • Hotel
    Only a short drive from the attractions of Chicago city centre, this hotel in Deerfield, Illinois, offers enjoyable facilities and services, as well as comfortable guestrooms. Hyatt Deerfield features
  • Renaissance Chicago North Shore Hotel

    8.1 Fabulous (760)
    • Hotel
    The Renaissance Chicago Northshore is located in Northbrook, and is a 13-minute drive from Skokie. It has an indoor pool, and offers spacious guestrooms with flat-screen TVs. Rooms at the Chicago Northshore
  • Residence Inn Chicago Deerfield

    8.2 Fabulous (177)
    • Hotel
    One of our bestsellers in Deerfield! Chicago Botanic Gardens is less than 3 miles from this Illinois hotel. Featuring an outdoor pool and a fitness centre, this hotel offers spacious guest studios with
  • Courtyard by Marriott Chicago Deerfield

    7 Very Good (74)
    • Hotel
    Situated in the business district, this hotel is within 3 miles (5 km) of Sportsman's Country Club, Northbrook Sports Complex and Northbrook Village Hall. Chicago Botanic Garden and Chevy Chase Country

The best places to stay in Highland Park

Book an apartment in Highland Park and choose the right accommodation for your needs

  • Longmeadow cottage / reno in process - update soon

    9 Exceptional (30)
    • 4 Guests · 1Bedroom
    Welcome to the cottage at Longmeadow. A tranquil escape from the city hustle of Downtown Chicago. Enjoy the serene setting while close proximity to town amenities, public transit and beautiful trails and
  • Entire House available for families and pets!

    9 Exceptional (46)
    • 5 Guests · 3Bedrooms
    Nice, remodeled ranch home with charm and modern amenities. Near highway and downtown Highland Park. Great for visiting relatives in the northern ‘burbs, near military bases for graduations, etc. Alexa
  • Rejuvenate and Relax in the North Shore

    10 Exceptional (30)
    • 12 Guests · 4Bedrooms
    Set in the midst of an affluent neighborhood, this spacious and sunny four bedroom retreat offers all the comforts of a home away from home. With it's perfect location close to Lake Michigan, Chicago Botanical
  • Ravinia / Amethyst

    9 Exceptional (16)
    • 4 Guests · 1Bedroom
    483 Roger Williams Avenue, 2nd floor, Highland Park, IL (Phone number hidden by Airbnb) is in downtown Ravinia, Steps from Ravinia Metra stop, a couple blocks from Ravinia's main gate. Its California
  • Northbrook Mansion

    9.3 Exceptional (4)
    • 14 Guests · 6Bedrooms
    Great getaway for a personal or business trip. This 6000 sf mansion boasts luxury with an open floor plan, large room sizes including a huge kitchen with a breakfast bar, kitchenette table, separate bar
  • A secluded room w its own entrance in a house

    • 2 Guests · 1Bedroom
    Come to our sunny and modern home in a quiet neighborhood. Our home is 5 min away from Ravinia Festival and Chicago Botanic Garden. Two blocks away from the bike path. 8 minutes from downtown Highland

Farmhouse or Hotel? Choose from the best offers

Choose the accommodation tailor-made for you for your next vacation: sleep in a farmhouse or sleep in a hotel?

  • Farmstays in Highland Park
    Farmstays in Highland Park
  • Hotels in Highland Park
    Hotels in Highland Park