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Vacation rentals in Highwood

Vacation rentals in Highwood

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Highwood

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

  • Room near Naval Base, Rosalind Franklin, lake (A)
    SUPERHOSTPrivate room · 3 guests · 1 bed · 1 shared bathroom
    Room near Naval Base, Rosalind Franklin, lake (A)

    Cozy home that is walking distance to the beach, shops, restaurants, and the Metra train. Close to Lake Forest and Lake Bluff downtown area, the Naval Base in North Chicago, Ravinia, Rosalind Franklin University, Lake Forest College, and more! - see more info and tips below

    What guests are saying:

    “This is a perfect place for either a short or long term stay. The rooms are extremely clean and have many amenities that makes you feel at home. The living room makes you feel like at nature, and the bathroom is extremely clean. All amenities are provided in sufficient amounts. There is a small poodle and a cat, both of which are gentle and extremely friendly. In sum, this place is a gem!”

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

  • Mid-Century Luxury w/ Chicago Just 35 Miles Away!
    Private room · 2 guests · 1 bed · 1 private bathroom
    Mid-Century Luxury w/ Chicago Just 35 Miles Away!

    Enjoy the luxury of a mid-century home nestled in woods, only 35 miles N of Chicago and 20 miles W of O'Hare. This private bedroom suite available w/ prvt bathroom & entrance in spacious 4000 sq ft home with access to kitchen & laundry room all on one floor. Comfortably accommodates 2 guests w/ 2 other bedrooms available under different listing. Enjoy TV, WiFi, closet space, work desk and other amenities. City trains are a 5 minute walk away. Come stay with us, morning tea is on us!

    What guests are saying:

    “Estelle's AirBnB was everything I had hoped for. I needed a place to stay on a trip to WI, and her house was the perfect choice. Conveniently located off I-294, Estelle provided excellent directions. Her house is on a private road which added a nice respite from the busy road trip. My room was more of a suite with bedroom, sitting area and large walk-in shower. She greeted me at the door and I instantly felt at ease. If I ever have another trip planned that gives me the opportunity to stay at her AirBnB, I will definitely be there.”

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Highwood holiday rentals

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

Other great holiday rentals in Highwood

Spacious 1BR Condo — 5min walk Shops & Restaurants
SUPERHOSTEntire apartment
Spacious 1BR Condo — 5min walk Shops & Restaurants
Price:£31 / night
Master qtr close to nature & easy urban facilities
SUPERHOSTEntire guest suite
Master qtr close to nature & easy urban facilities
Price:£57 / night
2 bed condo in quiet Chicago suburb. Portillos!
Entire apartment
2 bed condo in quiet Chicago suburb. Portillos!
Price:£45 / night
Perfect for Individual Travelers #1
SUPERHOSTPrivate room
Perfect for Individual Travelers #1
Price:£38 / night
Private Bedroom near Metra, 20 min to Airport
SUPERHOSTPrivate room
Private Bedroom near Metra, 20 min to Airport
Price:£21 / night
Warm Southern Exposure Sleeping Room
Private room
Warm Southern Exposure Sleeping Room
Price:£21 / night
Comfy Spacious  O'hare Mount Prospect AirBnB
SUPERHOSTPrivate room
Comfy Spacious O'hare Mount Prospect AirBnB
Price:£32 / night
Upstairs Suite
SUPERHOSTPrivate room
Upstairs Suite
Price:£33 / night
Beautiful Evanston condo by the lake
SUPERHOSTEntire apartment
Beautiful Evanston condo by the lake
Price:£78 / night
Bright, Beautiful, Spacious, just steps to beach
SUPERHOSTEntire flat
Bright, Beautiful, Spacious, just steps to beach
Price:£76 / night
Huge Room in Stunning Victorian across from NU
SUPERHOSTPrivate room
Huge Room in Stunning Victorian across from NU
Price:£61 / night
Perfect place for solo traveler
SUPERHOSTPrivate room
Perfect place for solo traveler
Price:£39 / night
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