Highwood holiday rentals

From simple studios to luxe lofts, find holiday rentals that are right for you on Airbnb.

Holiday rentals in Highwood

$119 NZD Big & Beautiful 2 Bedroom Private English Basement
13 reviews

Fully finished and recently remodeled ENGLISH BASEMENT with PRIVATE entrance & pond-view PATIO. 2 bedroom, 1.5 bathroom, kitchenette, microwave, 2 small refrigerators, coffeemak... read more
$91 NZD Near NU & EV hospital
5 reviews

Spacious 1 bedroom apartment, great part of town! Perfect for long term temporary stays. Available only during college school year, preferred minimum stay is one week, discount ... read more
$209 NZD Designer Lake house on Private Gages Lake and Park
15 reviews

Stunning open, airy, modern lake house with amazing views. Wake up to a light filled home to the smells of coffee and a loft feel. Very large sliding doors open to a third level... read more
$125 NZD Downtown HP Romantic Getaway
23 reviews

Looking for the perfect place to spend the weekend with your significant other? You found it! Located on Central Ave in quaint downtown Highland Park, minutes drive from the bea... read more
$70 NZD Private Bedroom in Wheeling
1 review

Our quite, comfy private home will be a peaceful retreat for you. Private Queen size bed on second floor with the bathroom right next door. You will be be just 20 minutes from O... read more
$67 NZD Cozy Room Private Bathroom Full SizeBed-Near Metra
37 reviews

Beautiful house in upscale NW suburban of Chicago. 20 mil to Airport, 2 min to Metra train that runs to Chicago and Airport, 5 min to I-94/294 and a shopping mall. The room with... read more

Favourite Highwood holiday rentals

$105 NZD The Lennon Room
8 reviews

On a very quiet street and surrounded by centennial trees, stands this beautiful 19th century Arts and Crafts house. It’s located at the corner of Sheridan Rd, just a block away... read more
$83 NZD Private Room at custom-built home.
11 reviews

Beautiful house built at former golf course, surrounded by natural trails and wild life, located at NW suburban of Chicago. We offer a private bedroom with queen bed and privat... read more
$105 NZD Modern and Comfortable Private Unit
19 reviews

Modern private unit in townhouse near downtown Libertyville and near shopping malls. Close to train and expressway direct to Chicago & airport. Easy car ride to Wisconsin, busi... read more
$140 NZD The Castle - Library Suite
3 reviews

Private wing with ample privacy. 2 bedroom suite connected by a common, full bathroom opens up to The Castle Library complete with personal HVAC controls, fireplace and outdoor... read more
$91 NZD Welcoming Private Suite in Lake Forest
4 reviews

Welcome to your own private suite within our house. You'll be super close to trains (to Chicago), as well as local amenities and businesses, idea for Lake Forest College, Lake F... read more
$56 NZD Wheeling Private Bedroom 2 with lock
11 reviews

Our home is just 20 minutes from O'Hare International Airport and under 2 miles away from the Metra stop that takes you directly into downtown Chicago. The nearest grocery store... read more

More holiday rentals in Highwood

$140 NZD HP MCM 2 Rooms & Bath Private Wing
38 reviews

Private guest wing of a beautiful Usonian/Mid Century Modern home with 2 rooms and private bathroom. Both rooms have been recently redecorated with fresh paint and new bedding. ... read more

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