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Highwood Holiday 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 holiday 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 HK$777
HK$1,538 total
includes taxes & fees
30 Sept - 1 Oct
Stunning & Stylish Downtown Studio - Highland Park
A modern house with a covered porch, large windows, and a well-maintained garden with various plants and flowers.

2. 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 HK$911
HK$1,672 total
includes taxes & fees
30 Sept - 1 Oct
Master qtr close to nature & easy urban facilities
A hotel room with a bed, two pillows, a nightstand with a lamp, and two abstract paintings on the wall.

3. 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 HK$698
HK$1,364 total
includes taxes & fees
5 Oct - 6 Oct
Chic Studio - In Downtown Highland Park, by Metra
A green door with a window above it, a sign reading "716 - 720 Central Ave," and the number "716" on the wall.

4. 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 HK$541
HK$1,239 total
includes taxes & fees
25 Oct - 26 Oct
Chic Studio in Downtown Highland Park near Metra
An outdoor patio with brick flooring, a grill, and a table with chairs.

5. 1 King Bed | Non-Smoking, Kitchen

1 King Bed | Non-Smoking, Kitchen
Chicago
9.6 out of 10, Exceptional, (15 reviews)
"Everything nice neat and clean"
United States
Anonymous traveller
The price is HK$635
HK$702 total
includes taxes & fees
18 Oct - 19 Oct
1 King Bed | Non-Smoking, Kitchen
A building with a stone facade and a large window displaying the text 'LAUNDRY MAT'.

6. 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 traveller
The price is HK$539
HK$650 total
includes taxes & fees
4 Oct - 5 Oct
King Bed Non-Smoking
A modern living room with a sofa, a blue armchair, a coffee table, and a TV mounted on the wall.

7. The Beach Park Retreat

The Beach Park Retreat
Beach Park
10.0 out of 10, Exceptional, (1 review)
"The host, Hugo, was friendly and answered questions promptly, the apartment was spacious and well maintained. The kitchen had everything we needed for a weekend trip. I would recommend this property to anyone staying in the area."
United States
Sara
The price is HK$855
HK$1,987 total
includes taxes & fees
6 Oct - 7 Oct
The Beach Park Retreat
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.

8. 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 traveller
The price is HK$648
HK$717 total
includes taxes & fees
18 Oct - 19 Oct
Studio 6 Vernon Hills|ADA Queen bed,RI Shower,Nsmk|Kitchen
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|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 traveller
The price is HK$601
HK$665 total
includes taxes & fees
18 Oct - 19 Oct
Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen
Welcome home! Enjoy the charming entrance that sets the tone for your stay.

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

Cozy Studio w/ Breakfast | Business Center & Pool
Glenview
The price is HK$1,287
HK$1,617 total
includes taxes & fees
18 Oct - 19 Oct
Cozy Studio w/ Breakfast | Business Center & Pool
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. 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 traveller
The price is HK$601
HK$665 total
includes taxes & fees
18 Oct - 19 Oct
1 King Bed | Non-Smoking, Kitchen, Shower
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 traveller
The price is HK$681
HK$754 total
includes taxes & fees
18 Oct - 19 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 HK$1,310
HK$2,951 total
includes taxes & fees
29 Oct - 30 Oct
3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi
A two-story house with a stone chimney, a front porch with steps, and a flag.

14. 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 HK$1,059
HK$2,619 total
includes taxes & fees
5 Oct - 6 Oct
Quaint Bungalow, near Great Lakes Naval Base
A modern living room with a sofa, coffee table, and lamps. A staircase is visible in the background.

15. 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 HK$2,216
HK$4,762 total
includes taxes & fees
5 Oct - 6 Oct
6 Kings Ping-Pong Gazebo!
A patio area with outdoor seating and solar-powered lights.

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

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
South Evanston
10.0 out of 10, Exceptional, (57 reviews)
"Great apt, excellent host"
United States
Colleen B.
The price is HK$904
HK$2,046 total
includes taxes & fees
6 Oct - 7 Oct
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
A dining area with a round table, four chairs, a chandelier, and a kitchen with white cabinets and a countertop.

17. 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 HK$635
HK$1,461 total
includes taxes & fees
30 Sept - 1 Oct
1-Bedroom Pad | Cozy + All-Set
A modern kitchen with white cabinets, a large island, a microwave, and a dining area with a chair and table.

18. Recharge in This Charming 1BR Apt

Recharge in This Charming 1BR Apt
Arlington Heights
8.6 out of 10, Excellent, (4 reviews)
"Nice for the price. Excellent location."
United States
Al E.
The price is HK$604
HK$1,867 total
includes taxes & fees
30 Sept - 1 Oct
Recharge in This Charming 1BR Apt
A kitchen with a stainless steel stove, oven, and microwave. There is a roll of paper towels, a kettle, and a coffee maker on the counter.

19. 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 HK$792
HK$1,802 total
includes taxes & fees
5 Oct - 6 Oct
Well-Equipped 2BR Unit with Parking
An outdoor patio area with a wooden fence, outdoor seating with chairs and a table, and multiple ground lamps.

20. Sunny Work From Home Apt: Near Northwestern-Chicago-Beaches-Loyola

Sunny Work From Home Apt: Near Northwestern-Chicago-Beaches-Loyola
South Evanston
10.0 out of 10, Exceptional, (9 reviews)
"It was a great experience! Very nice and clean place. Advertised exactly as seen. Parking was very easy and the location was great. Overall, would definitely stay again!"
United States
Sophia P.
The price is HK$904
HK$2,105 total
includes taxes & fees
1 Oct - 2 Oct
Sunny Work From Home Apt: Near Northwestern-Chicago-Beaches-Loyola
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

DoubleTree by Hilton Chicago O'Hare Airport - Rosemont

DoubleTree by Hilton Chicago O'Hare Airport - Rosemont

10/10 Excellent
"Great stay!"
Erik A. 3-night trip
Posted less than an hour ago
DoubleTree by Hilton Chicago O'Hare Airport - Rosemont

Find out more about Highwood

Search for holiday rentals in Highwood on Expedia! You can easily find your home rentals, villas, holiday apartments in Highwood using one of the methods below:

  • View our selection of featured holiday rentals in Highwood
  • Use the map to find apartments and other holiday homes in the Highwood neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Highwood while they last

Look no further and take a look at our great range of rental properties in Highwood!

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 Chicago Botanic Garden. In the wider area, you’ll find Lake Forest College and Ravinia Pavilion.

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.