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Highwood Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Highwood vacation rentals

A modern kitchen with white cabinets, a microwave, and a stove. There is a yellow armchair with a white pillow next to a large gray and white flower painting on the wall.

1. Stunning & Stylish Downtown Studio - Highland Park

Stunning & Stylish Downtown Studio - Highland Park
Highland Park
8.4 out of 10, Very good, (7 reviews)
"Great location, quiet area, easy walking into town for breakfast etc"
United States
Tom B.
The price is AED 290
AED 638 total
includes taxes & fees
1 Nov - 2 Nov
Stunning & Stylish Downtown Studio - Highland Park
A hotel room with a bed, two pillows, a nightstand with a lamp, and two abstract paintings on the wall.

2. Chic Studio - In Downtown Highland Park, by Metra

Chic Studio - In Downtown Highland Park, by Metra
Highland Park
8.4 out of 10, Very good, (16 reviews)
"I enjoyed my stay at this property. It is in a great location, very unique and super clean! The host is really kind and helpful. "
United States
Deborah
The price is AED 290
AED 599 total
includes taxes & fees
1 Nov - 2 Nov
Chic Studio - In Downtown Highland Park, by Metra
A modern house with a covered porch, large windows, and a well-maintained garden with various plants and flowers.

3. Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (87 reviews)
"Great spot, safe, clean, and beautiful environment would highly recommend!"
United States
Chris F.
The price is AED 437
AED 810 total
includes taxes & fees
19 Oct - 20 Oct
Master qtr close to nature & easy urban facilities
A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

4. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (274 reviews)
"Really helpful staff, really nice rooms."
United States
Archita
The price is AED 708
AED 810 total
includes taxes & fees
29 Oct - 30 Oct
The Gem Museum Suites
Welcome home! Enjoy the charming entrance that sets the tone for your stay.

5. Cozy Studio w/ Breakfast | Business Center & Pool

Cozy Studio w/ Breakfast | Business Center & Pool
Glenview
The price is AED 584
AED 748 total
includes taxes & fees
1 Nov - 2 Nov
Cozy Studio w/ Breakfast | Business Center & Pool
A green door with a window above it, a sign reading "716 - 720 Central Ave," and the number "716" on the wall.

6. Chic Studio in Downtown Highland Park near Metra

Chic Studio in Downtown Highland Park near Metra
Highland Park
7.4 out of 10, Good, (6 reviews)
"Nice and cozy! Easy access to the surrounding area."
United States
Jason H.
The price is AED 253
AED 580 total
includes taxes & fees
20 Oct - 21 Oct
Chic Studio in Downtown Highland Park near Metra
An outdoor patio with brick flooring, a grill, and a table with chairs.

7. 1 King Bed | Non-Smoking, Kitchen

1 King Bed | Non-Smoking, Kitchen
Chicago
9.0 out of 10, Wonderful, (16 reviews)
"Everything nice neat and clean"
United States
Anonymous traveler
The price is AED 274
AED 304 total
includes taxes & fees
25 Oct - 26 Oct
1 King Bed | Non-Smoking, Kitchen
A modern living room with a sofa, coffee table, and lamps. A staircase is visible in the background.

8. 6 Kings Ping-Pong Gazebo!

6 Kings Ping-Pong Gazebo!
Northbrook
9.0 out of 10, Wonderful, (7 reviews)
"Hosts were great. Very accommodating to our needs and quick to respond. I will stay again!"
United States
Cj Y.
The price is AED 1,138
AED 2,494 total
includes taxes & fees
4 Oct - 5 Oct
6 Kings Ping-Pong Gazebo!
A hotel room with a bed, two bedside lamps, a chair, a nightstand, a framed picture on the wall, and a window with a view.

9. Studio 6 Vernon Hills|ADA Queen bed,RI Shower,Nsmk|Kitchen

Studio 6 Vernon Hills|ADA Queen bed,RI Shower,Nsmk|Kitchen
Chicago
10.0 out of 10, Exceptional, (15 reviews)
"Big room with a kitchen,"
United States
Anonymous traveler
The price is AED 280
AED 310 total
includes taxes & fees
25 Oct - 26 Oct
Studio 6 Vernon Hills|ADA Queen bed,RI Shower,Nsmk|Kitchen
A building with a stone facade and a large window displaying the text 'LAUNDRY MAT'.

10. King Bed Non-Smoking

King Bed Non-Smoking
Chicago
10.0 out of 10, Exceptional, (288 reviews)
"Clean room and friendly staff made it a good stay."
United States
Anonymous traveler
The price is AED 251
AED 303 total
includes taxes & fees
5 Oct - 6 Oct
King Bed Non-Smoking
A hotel room with a bed, two bedside lamps, a chair, a nightstand, a framed picture on the wall, and a window with a view.

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

Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen
Chicago
9.6 out of 10, Exceptional, (17 reviews)
"Great place to stay"
United States
Anonymous traveler
The price is AED 259
AED 286 total
includes taxes & fees
25 Oct - 26 Oct
Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen
A hotel room with two beds, a framed picture on the wall, and a nightstand with a lamp.

12. Spacious 2 Queen Beds,Nsmk|Kitchen|Studio 6 Vernon Hills

Spacious 2 Queen Beds,Nsmk|Kitchen|Studio 6 Vernon Hills
Chicago
9.0 out of 10, Wonderful, (23 reviews)
"Good place to stay,,"
United States
Anonymous traveler
The price is AED 296
AED 328 total
includes taxes & fees
25 Oct - 26 Oct
Spacious 2 Queen Beds,Nsmk|Kitchen|Studio 6 Vernon Hills
A bedroom with a large bed, two bedside tables, and decorative wall mirrors.

13. 3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi

3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi
Waukegan
9.4 out of 10, Exceptional, (29 reviews)
"Excellent location for Navy Graduation and clean. 5 minutes to the Metra Train. Property owner is very responsive and flexible. Beds were comfortable and double sink in the 1 bathroom was a plus."
United States
Shannon W.
The price is AED 588
AED 1,411 total
includes taxes & fees
1 Nov - 2 Nov
3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi
A hotel room with a bed, two bedside lamps, a chair, a nightstand, a framed picture on the wall, and a window with a view.

14. 1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Chicago
9.0 out of 10, Wonderful, (16 reviews)
"Room was okay, Very basic,"
United States
Anonymous traveler
The price is AED 259
AED 286 total
includes taxes & fees
25 Oct - 26 Oct
1 King Bed | Non-Smoking, Kitchen, Shower
A two-story house with a stone chimney, a front porch with steps, and a flag.

15. Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base
Mundelein
9.8 out of 10, Exceptional, (75 reviews)
"Fantastic location. Very clean. Great/quick communication with host. Definitely recommend!"
United States
Jaclyn Z.
The price is AED 496
AED 1,296 total
includes taxes & fees
5 Oct - 6 Oct
Quaint Bungalow, near Great Lakes Naval Base
A room with a white desk, a white chair, a round mirror, a clock, and a lamp.

16. Well-Equipped 2BR Unit with Parking

Well-Equipped 2BR Unit with Parking
North Evanston
10.0 out of 10, Exceptional, (5 reviews)
"Great place. Super clean and easy off street parking. Thanks !"
United States
Ann N.
The price is AED 364
AED 859 total
includes taxes & fees
5 Oct - 6 Oct
Well-Equipped 2BR Unit with Parking
Interior

17. Modern 3-bedroom house in tranquil North Chicago near Great Lakes Navy Base

Modern 3-bedroom house in tranquil North Chicago near Great Lakes Navy Base
North Chicago
7.8 out of 10, Good, (6 reviews)
"Rented this property for my sons navy graduation, Base was only 6 minutes from the home. Tons of places to eat and shop no more then 15 minutes away. The house was super cute, very clean. we flew in at 10am and without even having to ask the host reached out and let us know it was ready for check in a few hours early which was great. left some packaged up congrats grad decor that hopefully didnt get thrown out and the next navy fam can use. "
United States
Linda U.
The price is AED 874
AED 2,157 total
includes taxes & fees
26 Oct - 27 Oct
Modern 3-bedroom house in tranquil North Chicago near Great Lakes Navy Base
A bedroom with a bed, a ceiling fan, a radiator, a window with blinds, and a potted plant.

18. Spacious 2BR Close to it All - Chic Apt in Skokie

Spacious 2BR Close to it All - Chic Apt in Skokie
West Dempster
9.0 out of 10, Wonderful, (2 reviews)
"Excellent communication with the host. Easy and secure access to the unit. Well furnished and perfect for my trip. So clean! "
United States
Jean W.
The price is AED 599
AED 1,120 total
includes taxes & fees
14 Oct - 15 Oct
Spacious 2BR Close to it All - Chic Apt in Skokie
A living room with a sofa, a coffee table, a TV stand, and a plant.

19. Chic 1BR Apt -Arlington Heights

Chic 1BR Apt -Arlington Heights
Arlington Heights
8.0 out of 10, Very good, (1 review)
"Parking was a problem "
United States
Brian W.
The price is AED 441
AED 1,079 total
includes taxes & fees
4 Oct - 5 Oct
Chic 1BR Apt -Arlington Heights
A dining area with a round table, four chairs, a chandelier, and a kitchen with white cabinets and a countertop.

20. 1-Bedroom Pad | Cozy + All-Set

1-Bedroom Pad | Cozy + All-Set
West Dempster
8.0 out of 10, Very good, (2 reviews)
"This was a great space. The location was perfect and we had everthing we needed. We would definitely stay here again. "
United States
Amanda M.
The price is AED 353
AED 757 total
includes taxes & fees
1 Nov - 2 Nov
1-Bedroom Pad | Cozy + All-Set
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

Sheraton Suites Chicago O'Hare

Sheraton Suites Chicago O'Hare

10/10 Excellent
"This hotel & room was very clean. The staff from shuttle operators, front desk and housekeepers were all very friendly, kind and helpful. The hotel has a flight restaurant in the middle on the bottom floor that serves amazing breakfast. The parking is very spacious and can be added to your stay."
Opallina 1-night trip
Posted 1 hour ago
Sheraton Suites Chicago O'Hare

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?

Sleeps 18 • 8BR • Game Room • Gym • Theater: This vacation home rental near Highwood offers a pool table, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 8 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

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 Lake Forest College and Ravinia Pavilion.

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.