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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 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 AED 437
AED 810 total
includes taxes & fees
19 Oct - 20 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 AED 290
AED 599 total
includes taxes & fees
1 Nov - 2 Nov
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 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.

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 traveler
The price is AED 274
AED 304 total
includes taxes & fees
25 Oct - 26 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 traveler
The price is AED 251
AED 303 total
includes taxes & fees
5 Oct - 6 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 AED 400
AED 930 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 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 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 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
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 AED 584
AED 748 total
includes taxes & fees
1 Nov - 2 Nov
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 traveler
The price is AED 259
AED 286 total
includes taxes & fees
25 Oct - 26 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 traveler
The price is AED 309
AED 341 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 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 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 AED 496
AED 1,296 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 AED 1,149
AED 2,499 total
includes taxes & fees
1 Nov - 2 Nov
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 AED 443
AED 1,021 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 AED 437
AED 863 total
includes taxes & fees
13 Oct - 14 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 AED 444
AED 1,091 total
includes taxes & fees
5 Oct - 6 Oct
Recharge in This Charming 1BR Apt
A room with a white desk, a white chair, a round mirror, a clock, and a lamp.

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 AED 364
AED 859 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 AED 443
AED 1,021 total
includes taxes & fees
29 Oct - 30 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

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

10/10 Excellent
"Breakfast was good. Staff was friendly."
Ariel 3-night trip
Posted 15 hours ago
Crowne Plaza Chicago Ohare Hotel & Conf Ctr 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?

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.