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Highwood Vacation Rentals

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Our top choices for Highwood vacation rentals

Exterior detail

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 AED 496
AED 1,296 total
includes taxes & fees
5 Jul - 6 Jul
Quaint Bungalow, near Great Lakes Naval Base
Property grounds

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 AED 526
AED 1,261 total
includes taxes & fees
5 Jul - 6 Jul
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
Exterior detail

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 AED 382
AED 720 total
includes taxes & fees
2 Jul - 3 Jul
Chic Studio in Downtown Highland Park near Metra
1 bedroom

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 traveler
The price is AED 415
AED 460 total
includes taxes & fees
1 Aug - 2 Aug
Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen
Smart TV, computer monitors

Modern 1BR w/ Workspace near O'Hare

Modern 1BR w/ Workspace near O'Hare
O'Hare
Modern 1BR w/ Workspace near O'Hare
Outdoor spa tub

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, (12 reviews)
"Very nice little spot... Host was absolutely wonderful!!! Definitely stay here again!"
United States
Adam B.
The price is AED 406
AED 690 total
includes taxes & fees
7 Jul - 8 Jul
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
Exterior detail

Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (84 reviews)
"nice little place! quiet area "
United States
Nayeli A.
The price is AED 413
AED 773 total
includes taxes & fees
6 Jul - 7 Jul
Master qtr close to nature & easy urban facilities
Terrace/patio

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 AED 413
AED 925 total
includes taxes & fees
6 Jul - 7 Jul
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
1 bedroom, iron/ironing board, free WiFi, bed sheets

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 AED 446
AED 777 total
includes taxes & fees
27 Jul - 28 Jul
Cozy studio in Andersonville Chicago
Paper towels

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)
"Great place! "
United States
Isabella T.
The price is AED 496
AED 931 total
includes taxes & fees
4 Jul - 5 Jul
Just remodeled apartment close to airport and mall
Fridge, microwave, oven, stovetop

Mins from O'Hare • Safe Location • Private Parking

Mins from O'Hare • Safe Location • Private Parking
O'Hare
The price is AED 250
AED 1,069 total
includes taxes & fees
7 Jul - 8 Jul
Mins from O'Hare • Safe Location • Private Parking
Fridge, microwave, oven, stovetop

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 AED 459
AED 1,255 total
includes taxes & fees
2 Jul - 3 Jul
Cozy apartment with AC and WiFi in awesome Chicago
TV

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

2BR • Newly Furnished Modern Apt • Near O'Hare
O'Hare
The price is AED 353
AED 1,451 total
includes taxes & fees
7 Jul - 8 Jul
2BR • Newly Furnished Modern Apt • Near O'Hare
Interior

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 AED 463
AED 895 total
includes taxes & fees
6 Jul - 7 Jul
Apartment Attached to a 1900 historic Farm house
Smart TV

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 AED 489
AED 1,024 total
includes taxes & fees
7 Jul - 8 Jul
Cute & Cozy, 1bd Condo Apartment/townhouse
Exterior detail

King Bed Non-Smoking

King Bed Non-Smoking
Chicago
The price is AED 415
AED 490 total
includes taxes & fees
13 Jul - 14 Jul
King Bed Non-Smoking
Interior

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 AED 375
AED 1,215 total
includes taxes & fees
27 Jul - 28 Jul
Modern Condo • Safe Chicago Stay Near O’Hare
Fridge, microwave, oven, stovetop

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 AED 683
AED 2,499 total
includes taxes & fees
6 Jul - 7 Jul
Family Stay with Game Garage, Fire Pit, Streaming TVs and Private Yard
1 bedroom, desk, iron/ironing board, WiFi

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 AED 309
AED 899 total
includes taxes & fees
7 Jul - 8 Jul
Elegant Style Loft Montrose|13 mins DT|4 mins Lake
Interior

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 AED 206
AED 1,008 total
includes taxes & fees
13 Jul - 14 Jul
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

Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

10/10 Excellent
"Clean , in general all service"
Lilia 1-night trip
Posted 3 hours ago
Holiday Inn Chicago O'Hare – Rosemont by IHG

Frequently asked questions

Are there vacation rentals in Highwood?

Yes, there are vacation rentals where you'll be just 12.7 mi (20.4 km) from Six Flags Great America, offering you a more remote option to escape the hustle and bustle. Highwood is known for its shopping and restaurants.

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

Pleasant 3-bedroom house with occupied basement separate entrance.: This vacation home rental near 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 larger area, you’ll find Naval Base Great Lakes and Lake Forest College.

What are vacation rentals like in Highwood?

Vacation rentals are private properties you can reserve for a short or long stay in Highwood. Vacation rentals offer extras such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for family trips.