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Vacation rentals in Highland Park

Vacation rentals in Highland Park

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Highland Park

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • Safe private retreat on two acres with heated pool
    SUPERHOSTEntire house · 14 guests · 6 beds · 4 baths
    Safe private retreat on two acres with heated pool

    In the prestigious affluent Architectural point of Highland Park. Private zen retreat on a two acre estate. Private pool without Lifeguard will be open during summers for guests. Guests will swim at their own risk without any liability to host. Diving pool (12 Feet at the deepest) and 3 feet at shallowest. Adult supervision for kids required. Close to Ravinia, Naval base, botanical gardens and conveniently located. Train to downtown in 35-40 minutes. O'hare is 20-25 minutes by car.

    What guests are saying:

    “Kailash is such a gracious and wonderful host! He accommodated all our needs, even last minute ones. He gave us many tips as to what was available around the area to make our stay as great as possible. The house was wonderful, just as described! It was very neat and clean and had welcoming touches. We even got a lovely welcome gift basket. Check-in was easy with no hassle. There were 12 of us during this trip and the house was more than sufficient for our needs. We truly felt at home during the week that we were there. You won't regret staying at this place, I can assure you that!”

  • Rejuvenate and Relax in the North Shore
    SUPERHOSTEntire house · 12 guests · 7 beds · 2.5 baths
    Rejuvenate and Relax in the North Shore

    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 Garden, Ravinia, Naval Base, and Six Flags Great America to name a few, our family home is within reach to Chicago as well. If you feel very adventurous, just leave your car in garage, pick up a bike and ride the Lake Shore Bike trail all the way to downtown Chicago, enjoying the beautiful scenery. If you feel less adventures but still would like to enjoy beautiful scenery, you can do it by taking a train. Metra can get you downtown Chicago in less than 45 min. and the stop is within walking distance.

    What guests are saying:

    “Thank you to Lana and Luca for an amazing stay. The kitchen and dining table are huge, which was great for a big family meal that we made together. The hallway closet upstairs was packed full of clean towels. Communication was excellent. We really appreciated the space, and it is definitely our first choice to book again for our next yearly family get-together in Chicago.”

  • Perfect for Individual Travelers #1
    SUPERHOSTPrivate room · 1 guest · 1 bed · 1 shared bath
    Perfect for Individual Travelers #1

    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, this room creates a soothing ambience that is perfect for rest and relaxation.

    What guests are saying:

    “Nina’s place is the most beautiful space I ever stayed. Its absolutely perfect like the picture. You literally can’t find a single flaw in her arrangements and hospitality. She provides all the amenities and is very welcoming. Her two dogs and the cat are adorable and are like treats to your eyes. Her husband Terry and business partner helped me settle in and made sure I was comfortable. The location, parking is very easy and follow the maps to find the house, its very accurate. I love the room and feels like you are in a doll house 😍 Thank you for hosting me and will surely come back soon again.”

Vacation rentals for every style

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Popular amenities for Highland Park vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Highland Park

Room near Naval Base, Rosalind Franklin, lake (A)
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Room near Naval Base, Rosalind Franklin, lake (A)
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Mid-Century Luxury w/ Chicago Just 35 Miles Away!
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Spacious 1BR Condo — 5min walk Shops & Restaurants
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Master qtr close to nature & easy urban facilities
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Unwind in a Charming Apartment with Skylights
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Private Bedroom near Metra, 20 min to Airport
SUPERHOSTPrivate room
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Comfy Spacious  O'hare Mount Prospect AirBnB
SUPERHOSTPrivate room
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Great neighborhood! Free parking. Bus on corner!
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Great neighborhood! Free parking. Bus on corner!
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Cozy Garden Unit in Quiet Neighborhood
SUPERHOSTEntire apartment
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Charming in-law suite w/ use of deck and yard
SUPERHOSTEntire guest suite
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Warm Southern Exposure Sleeping Room
Private room
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2 bed condo in quiet Chicago suburb. Portillos!
Entire condominium
2 bed condo in quiet Chicago suburb. Portillos!
Price:$76 CAD/night
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