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Highwood Holiday Rentals

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Our top choices for Highwood holiday rentals

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$506
includes taxes & fees
5 July - 6 July
Quaint Bungalow, near Great Lakes Naval Base

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
North Center
9.6 out of 10, Exceptional, (84 reviews)
"Great location for a short trip "
United States
Eric W.
The price is AU$488
includes taxes & fees
5 July - 6 July
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

Chic Studio in Downtown Highland Park near Metra

Chic Studio in Downtown Highland Park near Metra
Highland Park
8.0 out of 10, Very good, (4 reviews)
"Nice and cozy! Easy access to the surrounding area."
United States
Jason H.
The price is AU$270
includes taxes & fees
13 July - 14 July
Chic Studio in Downtown Highland Park near Metra

Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen

Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen
Chicago
10.0 out of 10, Exceptional, (16 reviews)
"Great place to stay"
United States
Anonymous traveller
The price is AU$171
includes taxes & fees
2 Aug - 3 Aug
Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen

Modern 1BR w/ Workspace near O'Hare

Modern 1BR w/ Workspace near O'Hare
O'Hare
The price is AU$398
includes taxes & fees
7 July - 8 July
Modern 1BR w/ Workspace near O'Hare

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, (13 reviews)
"Very nice little spot... Host was absolutely wonderful!!! Definitely stay here again!"
United States
Adam B.
The price is AU$275
includes taxes & fees
7 July - 8 July
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC

Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (85 reviews)
"nice little place! quiet area "
United States
Nayeli A.
The price is AU$313
includes taxes & fees
6 July - 7 July
Master qtr close to nature & easy urban facilities

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
South Evanston
10.0 out of 10, Exceptional, (50 reviews)
"The place was awesome - very clean !! Great location !! "
United States
John R.
The price is AU$367
includes taxes & fees
7 July - 8 July
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More

Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (83 reviews)
"Great stay i loved it"
United States
Cedes W.
The price is AU$276
includes taxes & fees
27 July - 28 July
Cozy studio in Andersonville Chicago

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, (17 reviews)
"Great place! "
United States
Isabella T.
The price is AU$368
includes taxes & fees
12 July - 13 July
Just remodeled apartment close to airport and mall

Mins from O'Hare • Safe Location • Private Parking

Mins from O'Hare • Safe Location • Private Parking
O'Hare
The price is AU$390
includes taxes & fees
7 July - 8 July
Mins from O'Hare • Safe Location • Private Parking

Cozy apartment with AC and WiFi in awesome Chicago

Cozy apartment with AC and WiFi in awesome Chicago
Rogers Park
7.6 out of 10, Good, (12 reviews)
"Cozy, private, clean. A quick walk to the train and busses. Would stay again."
United States
John D.
The price is AU$538
includes taxes & fees
5 July - 6 July
Cozy apartment with AC and WiFi in awesome Chicago

2BR • Newly Furnished Modern Apt • Near O'Hare

2BR • Newly Furnished Modern Apt • Near O'Hare
O'Hare
The price is AU$518
includes taxes & fees
6 July - 7 July
2BR • Newly Furnished Modern Apt • Near O'Hare

Apartment Attached to a 1900 historic Farm house

Apartment Attached to a 1900 historic Farm house
Old Mill Creek
8.6 out of 10, Excellent, (19 reviews)
"The place is very cozy and inviting. There was a smell we thought might have been cat urine on a blanket. Otherwise I'd recommend it."
United States
Matt H.
The price is AU$333
includes taxes & fees
8 July - 9 July
Apartment Attached to a 1900 historic Farm house

Cute & Cozy, 1bd Condo Apartment/townhouse

Cute & Cozy, 1bd Condo Apartment/townhouse
Zion
10.0 out of 10, Exceptional, (3 reviews)
"Great stay was clean and in a great location overall was a good experience!"
United States
Tristan P.
The price is AU$412
includes taxes & fees
12 July - 13 July
Cute & Cozy, 1bd Condo Apartment/townhouse

King Bed Non-Smoking

King Bed Non-Smoking
Chicago
The price is AU$152
includes taxes & fees
19 July - 20 July
King Bed Non-Smoking

Modern Condo • Safe Chicago Stay Near O’Hare

Modern Condo • Safe Chicago Stay Near O’Hare
O'Hare
10.0 out of 10, Exceptional, (1 review)
"The overall experience was fantastic. The unit was clean and well stocked to meet all my needs for the stay. Staff were very responsive and helpful with all inquires"
United States
Jatin P.
The price is AU$478
includes taxes & fees
3 Aug - 4 Aug
Modern Condo • Safe Chicago Stay Near O’Hare

Family Stay with Game Garage, Fire Pit, Streaming TVs and Private Yard

Family Stay with Game Garage, Fire Pit, Streaming TVs and Private Yard
Libertyville
The price is AU$951
includes taxes & fees
6 July - 7 July
Family Stay with Game Garage, Fire Pit, Streaming TVs and Private Yard

Elegant Style Loft Montrose|13 mins DT|4 mins Lake

Elegant Style Loft Montrose|13 mins DT|4 mins Lake
Uptown
8.6 out of 10, Excellent, (11 reviews)
"Great location and great place! "
United States
Ryinne P.
The price is AU$330
includes taxes & fees
7 July - 8 July
Elegant Style Loft Montrose|13 mins DT|4 mins Lake

Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace
Irving Park
10.0 out of 10, Exceptional, (4 reviews)
"Great location and easy on street parking. "
United States
Lori A.
The price is AU$611
includes taxes & fees
23 July - 24 July
Sleeps 7 • Huge Projector • Designated Workspace
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$190 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?

Pleasant 3-bedroom house with occupied basement separate entrance.: This holiday home rental outside of Highwood has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

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.