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Highwood Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Highwood vacation rentals

A bedroom with a bed, a wardrobe, a lamp, and a chair.

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 ￥12,506
￥27,515 total
includes taxes & fees
Nov 11 - Nov 12
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, (88 reviews)
"Great spot, safe, clean, and beautiful environment would highly recommend!"
United States
Chris F.
The price is ￥16,955
￥32,902 total
includes taxes & fees
Oct 19 - Oct 20
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 ￥11,715
￥24,999 total
includes taxes & fees
Nov 8 - Nov 9
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 ￥9,499
￥23,490 total
includes taxes & fees
Nov 8 - Nov 9
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
9.0 out of 10, Wonderful, (16 reviews)
"Everything nice neat and clean"
United States
Anonymous traveler
The price is ￥10,756
￥11,900 total
includes taxes & fees
Nov 8 - Nov 9
1 King Bed | Non-Smoking, Kitchen
Welcome home! Enjoy the charming entrance that sets the tone for your stay.

6. Accessible Suite | Kitchen, Free Breakfast & Pool

Accessible Suite | Kitchen, Free Breakfast & Pool
Glenview
The price is ￥28,588
￥36,605 total
includes taxes & fees
Oct 31 - Nov 1
Accessible Suite | Kitchen, Free Breakfast & Pool
A building with a stone facade and a large window displaying the text 'LAUNDRY MAT'.

7. 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 ￥10,690
￥12,894 total
includes taxes & fees
Oct 19 - Oct 20
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.

8. 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 ￥10,091
￥11,166 total
includes taxes & fees
Nov 8 - Nov 9
Studio 6 Vernon Hills|Relax Queen Bed,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|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 ￥11,020
￥12,192 total
includes taxes & fees
Nov 8 - Nov 9
Studio 6 Vernon Hills|ADA Queen bed,RI Shower,Nsmk|Kitchen
A hotel room with two beds, a framed picture on the wall, and a nightstand with a lamp.

10. 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 ￥11,662
￥12,903 total
includes taxes & fees
Nov 8 - Nov 9
Spacious 2 Queen Beds,Nsmk|Kitchen|Studio 6 Vernon Hills
A modern kitchen with white cabinetry, a central island with bar stools, a stove, oven, microwave, and a ceiling fan.

11. 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 ￥27,127
￥104,772 total
includes taxes & fees
Oct 14 - Oct 15
Family Stay with Game Garage, Fire Pit, Streaming TVs and Private Yard
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.

12. 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 ￥10,091
￥11,166 total
includes taxes & fees
Nov 8 - Nov 9
1 King Bed | Non-Smoking, Kitchen, Shower
A modern living room with a sofa, coffee table, and lamps. A staircase is visible in the background.

13. 6 Kings Ping-Pong Gazebo!

6 Kings Ping-Pong Gazebo!
Northbrook
8.4 out of 10, Very good, (8 reviews)
"Hosts were great. Very accommodating to our needs and quick to respond. I will stay again!"
United States
Cj Y.
The price is ￥42,642
￥98,399 total
includes taxes & fees
Nov 2 - Nov 3
6 Kings Ping-Pong Gazebo!
Welcome home! Enjoy the charming entrance that sets the tone for your stay.

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

Cozy Studio w/ Breakfast | Business Center & Pool
Glenview
The price is ￥27,741
￥35,482 total
includes taxes & fees
Nov 1 - Nov 2
Cozy Studio w/ Breakfast | Business Center & Pool
A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

15. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (286 reviews)
"Really helpful staff, really nice rooms."
United States
Archita
The price is ￥36,329
￥41,590 total
includes taxes & fees
Nov 12 - Nov 13
The Gem Museum Suites
A two-story house with a stone chimney, a front porch with steps, and a flag.

16. 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 ￥21,372
￥56,037 total
includes taxes & fees
Oct 25 - Oct 26
Quaint Bungalow, near Great Lakes Naval Base
A modern kitchen with white cabinets, a large island, a microwave, and a dining area with a chair and table.

17. 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 ￥14,912
￥41,595 total
includes taxes & fees
Oct 19 - Oct 20
Recharge in This Charming 1BR Apt
A bedroom with a large bed, two bedside tables, and decorative wall mirrors.

18. 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
9.6 out of 10, Exceptional, (31 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 ￥29,287
￥66,433 total
includes taxes & fees
Oct 17 - Oct 18
3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi
A patio area with outdoor seating and solar-powered lights.

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

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
South Evanston
10.0 out of 10, Exceptional, (59 reviews)
"Great apt, excellent host"
United States
Colleen B.
The price is ￥19,092
￥44,336 total
includes taxes & fees
Oct 25 - Oct 26
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
A bedroom with a bed, a ceiling fan, a radiator, a window with blinds, and a potted plant.

20. 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 ￥15,071
￥35,042 total
includes taxes & fees
Oct 14 - Oct 15
Spacious 2BR Close to it All - Chic Apt in Skokie
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

Comfort Inn & Suites Arlington Heights - Schaumburg

Comfort Inn & Suites Arlington Heights - Schaumburg

8/10 Good
"We had a great experience."
Prince 3-night trip
Posted 2 hours ago
Comfort Inn & Suites Arlington Heights - Schaumburg

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:

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

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.