Highwood Holiday Rentals

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Our top choices for Highwood holiday rentals

Uptown Studio Gem Sum

Uptown Studio Gem Sum
Uptown
7.8 out of 10, Good, (7 reviews)
"This studio is very clean and is located in a neighborhood with access to anything you would want to do or see. The stairway and halls are not pristine, but studio is good. Neighbors were quiet and seldom seen during my stay. Excellent restaurant right across the street and grocery nearby. Wrigley Field is easy walk. Check in was confusing for me, but it worked out. "
United States
Leah W.
The price is AU$276
includes taxes & fees
11 May - 12 May
Uptown Studio Gem Sum

Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base
Mundelein
9.8 out of 10, Exceptional, (72 reviews)
"We had a great stay! The area was peaceful and felt safe. "
United States
Yoselin V.
The price is AU$456
includes taxes & fees
10 May - 11 May
Quaint Bungalow, near Great Lakes Naval Base

Cute & Cozy, 1bd Condo Apartment/townhouse

Cute & Cozy, 1bd Condo Apartment/townhouse
Zion
10.0 out of 10, Exceptional, (2 reviews)
"The property was very clean and has a very relaxing feel to it. The owner was very responsive when I had any questions and was very helpful. "
United States
Caleb C.
The price is AU$390
includes taxes & fees
12 May - 13 May
Cute & Cozy, 1bd Condo Apartment/townhouse

Just remodeled apartment close to airport and mall

Just remodeled apartment close to airport and mall
Elk Grove Village
10.0 out of 10, Exceptional, (16 reviews)
"Very nice place to stay in secure neighborhood "
United States
Christina F.
The price is AU$378
includes taxes & fees
27 May - 28 May
Just remodeled apartment close to airport and mall

2-bedroom apartment just 2 minutes drive to Wrigley Field

2-bedroom apartment just 2 minutes drive to Wrigley Field
North Center
9.6 out of 10, Exceptional, (71 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is AU$485
includes taxes & fees
13 May - 14 May
2-bedroom apartment just 2 minutes drive to Wrigley Field

F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC

F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
Barrington
9.8 out of 10, Exceptional, (9 reviews)
"Very nice little spot... Host was absolutely wonderful!!! Definitely stay here again!"
United States
Adam B.
The price is AU$240
includes taxes & fees
10 May - 11 May
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC

Navy Family home -Near Lake 4BR Hot Tub

Navy Family home -Near Lake 4BR Hot Tub
Gages Lake
10.0 out of 10, Exceptional, (12 reviews)
"Nice location for our family attending our daughter's graduation from Navy Basic at Great Lakes. "
United States
Judson S.
The price is AU$932
includes taxes & fees
11 May - 12 May
Navy Family home -Near Lake 4BR Hot Tub

Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (80 reviews)
"Had a lovely stay in a beautiful home! The setting is very secluded and quiet."
United States
Kyle M.
The price is AU$274
includes taxes & fees
14 May - 15 May
Master qtr close to nature & easy urban facilities

Pine Beam Sloth Apartment next to Blue Line

Pine Beam Sloth Apartment next to Blue Line
Irving Park
10.0 out of 10, Exceptional, (6 reviews)
"Beautifully decorated, spotless unit. Conveniently located."
United States
Holly G.
The price is AU$387
includes taxes & fees
11 May - 12 May
Pine Beam Sloth Apartment next to Blue Line

Charming Sunlit 1BR Apartment

Charming Sunlit 1BR Apartment
Irving Park
9.0 out of 10, Wonderful, (14 reviews)
"Host was very attentive and answered all of our questions. It was very cozy and exactly as pictured."
United States
Brandon M.
The price is AU$285
includes taxes & fees
11 May - 12 May
Charming Sunlit 1BR Apartment

Cozy 1-Bedroom Apartment

Cozy 1-Bedroom Apartment
Portage Park
10.0 out of 10, Exceptional, (1 review)
"The place was great! It's stocked with the basics, bed and couch are comfy, and everything is clean. There were only a handful of times when I heard the upstairs neighbor, but nothing too crazy. The neighborhood itself is very cute and quiet, with good food and stores within walking distance. Street parking was easy. Thank you! "
United States
Sarah M.
The price is AU$275
includes taxes & fees
11 May - 12 May
Cozy 1-Bedroom Apartment

Stylish 1BR Stay in Irving Vibes

Stylish 1BR Stay in Irving Vibes
Irving Park
8.4 out of 10, Very good, (5 reviews)
"Great place to stay Comfy bed and setting"
United States
Steven
The price is AU$284
includes taxes & fees
11 May - 12 May
Stylish 1BR Stay in Irving Vibes

Sunlit Studio with City Charm

Sunlit Studio with City Charm
Rogers Park
8.0 out of 10, Very good, (11 reviews)
"Host was extremely welcoming and accommodating. They went out of their way to assure me that they were but a call away if there was anything we needed."
United States
Renee W.
The price is AU$244
includes taxes & fees
11 May - 12 May
Sunlit Studio with City Charm

Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (76 reviews)
"Great stay i loved it"
United States
Cedes W.
The price is AU$212
includes taxes & fees
11 May - 12 May
Cozy studio in Andersonville Chicago

Hot Tub Retreats

Hot Tub Retreats
Lake Villa
The price is AU$397
includes taxes & fees
10 May - 11 May
Hot Tub Retreats

Tiny Home Retreat with hot tub

Tiny Home Retreat with hot tub
Lake Villa
9.0 out of 10, Wonderful, (4 reviews)
"Amazing stay, great host! "
United States
Aaron L.
The price is AU$470
includes taxes & fees
14 May - 15 May
Tiny Home Retreat with hot tub

Great Layout – Spacious 2BR Apt

Great Layout – Spacious 2BR Apt
Rogers Park
9.2 out of 10, Wonderful, (11 reviews)
"Clean, comfortable, and would definitely stay again!"
United States
KM W.
The price is AU$414
includes taxes & fees
8 June - 9 June
Great Layout – Spacious 2BR Apt

Comfy Studio in Portage Park- Great Value!

Comfy Studio in Portage Park- Great Value!
Portage Park
10.0 out of 10, Exceptional, (1 review)
"The host was very friendly, helpful, and communicative. The apartment was clean and quiet. "
United States
Clifton C.
The price is AU$250
includes taxes & fees
12 May - 13 May
Comfy Studio in Portage Park- Great Value!

Comfortable 2BR Chicago Apt

Comfortable 2BR Chicago Apt
Albany Park
9.6 out of 10, Exceptional, (7 reviews)
"Perfect location for our trip. Very functional and comfortable. "
United States
Michael
The price is AU$391
includes taxes & fees
12 May - 13 May
Comfortable 2BR Chicago Apt

Trendy & Comfy Studio Unit

Trendy & Comfy Studio Unit
Portage Park
9.2 out of 10, Wonderful, (7 reviews)
"It was really a great place. Bb oo"
United States
Kate S.
The price is AU$252
includes taxes & fees
12 May - 13 May
Trendy & Comfy Studio Unit
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Highwood Hotel Reviews

Find out more about Highwood

Everything you need to know about Highwood holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Highwood holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Highwood holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Highwood holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Highwood. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Highwood holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Highwood holiday rentals we have selected for you start as low as AU$207 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Highwood rentals

At Expedia, we put the best Highwood holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Highwood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Highwood holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Highwood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Highwood?

Yes, we offer holiday rentals where you'll be just 12.7 mi (20.4 km) from Six Flags Great America, providing a more secluded option if you want peace and quiet. Highwood is known for its shopping and restaurants.

What are some of the best holiday rentals that Highwood has to offer?

Beach Park Estate: Chef's Kitchen, Nature, Fitness Room, Naval Base, Beach, Lake: This holiday home rental outside of Highwood offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 9 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a garden.

What can I see and do in Highwood?

While exploring the area, visit family-friendly sights like Six Flags Great America, or get outside and enjoy nature at Rosewood Beach. In the wider area, you’ll find Naval Base Great Lakes and Lake Forest College.

What are holiday rentals like in Highwood?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Highwood. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll have everything you want. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for a family trip.