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Vacation rentals in Highwood

Vacation rentals in Highwood

Find and book unique accommodations on Airbnb

Top-rated vacation 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 bath
    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!”

  • Master qtr close to nature & easy urban facilities
    SUPERHOSTEntire guest suite · 2 guests · 1 bed · 1 bath
    Master qtr close to nature & easy urban facilities

    This amazing prairie style home sits on 2 acre land surrounded by lush lawn and majestic oak trees - a nature lover's dream with unparalleled serenity. Vacation-like setting blends country-like quiet with nearby conveniences including shopping, trains, restaurants, highways, and major corporations - 5 MINS to I 294. 20 MINS to O'HARE; 5 Mins to Discover, Baxter headquarters; 10 MINS to Walgreens Deerfield campus, TRINITY INT'L UNIVERSITY; 15 MINS to Lake Forest Academy & Caterpillar HQ.

    What guests are saying:

    “This place is a fantastic getaway hideaway not too far from a Whole Foods and lots of things. No stove, but there is a microwave, fridge & kettle, and the hot tub is especially nice. Quiet, out of the way, and incredible closet space! Very easy check in/out & perfect communication from the host.”

  • Ideal Location in #AwesomeHeights
    SUPERHOSTEntire apartment · 2 guests · 1 bed · 1 bath
    Ideal Location in #AwesomeHeights

    Near the heart of downtown Arlington Heights and Arlington Park Racetrack. You can settle in at this cozy basement apartment with a super comfortable queen bed and all the amenities you’d need. Whether your visit to AH is for business or pleasure, city or suburbs, we look forward to accommodating you. The private apartment works great for people with a car or using public transit. We are convenient to the Metra station, AH restaurants, Arlington Park, NW Community Hospital & Woodfield Mall.

    What guests are saying:

    “This spot is a gem!! This basement suite was everything one could ask for in a space. It felt like home. Janet was super friendly. The neighborhood is lovely. Everything is within walking distance. I walked a few blocks to grab dinner and I felt very safe. The bed, couch, & fluffy chairs were all very comfortable. I love to read outside and this place has so many outdoor seating spots! I definitely hope to stay here again someday.”

Vacation rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Highwood vacation rentals

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

Other great vacation rentals in Highwood

SW Evanston Private, Quiet, Spacious Suite
SUPERHOSTEntire house
SW Evanston Private, Quiet, Spacious Suite
Price:$49 / night
Charming in-law suite w/ use of deck and yard
SUPERHOSTEntire guest suite
Charming in-law suite w/ use of deck and yard
Price:$95 / night
Spacious 1BR Condo — 5min walk Shops & Restaurants
SUPERHOSTEntire condominium
Spacious 1BR Condo — 5min walk Shops & Restaurants
Price:$43 / night
Mid-Century Luxury w/ Chicago Just 35 Miles Away!
Private room
Mid-Century Luxury w/ Chicago Just 35 Miles Away!
Price:$33 / night
Cozy Bedroom near public transportation
Private room
Cozy Bedroom near public transportation
Price:$35 / night
Your home away from home
Private room
Your home away from home
Price:$35 / night
Sweet Spot by the Water
Private room
Sweet Spot by the Water
Price:$45 / night
Cozy Garden Unit in Quiet Neighborhood
SUPERHOSTEntire apartment
Cozy Garden Unit in Quiet Neighborhood
Price:$75 / night
Garden View Queen Bed, Pet-Free, Allergy Sensitive
SUPERHOSTPrivate room
Garden View Queen Bed, Pet-Free, Allergy Sensitive
Price:$53 / night
Large Room - sleeps 4. Near public transportation
Private room
Large Room - sleeps 4. Near public transportation
Price:$35 / night
2 bed condo in quiet Chicago suburb. Portillos!
Entire condominium
2 bed condo in quiet Chicago suburb. Portillos!
Price:$56 / night
Warm Southern Exposure Sleeping Room
Private room
Warm Southern Exposure Sleeping Room
Price:$26 / night
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