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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 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.
$169 nightly
The price is $179
Nov 16 - Nov 17
Total with taxes and fees
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.
$196 nightly
The price is $208
Oct 27 - Oct 28
Total with taxes and fees
Master qtr close to nature & easy urban facilities
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.

3. 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
$66 nightly
The price is $73
Oct 19 - Oct 20
Total with taxes and fees
1 King Bed | Non-Smoking, Kitchen, Shower
A hotel room with a bed, two pillows, a nightstand with a lamp, and two abstract paintings on the wall.

4. 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
$149 nightly
The price is $158
Nov 8 - Nov 9
Total with taxes and fees
Chic Studio - In Downtown Highland Park, by Metra
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
$195 nightly
The price is $218
Nov 15 - Nov 16
Total with taxes and fees
Cozy Studio w/ Breakfast | Business Center & Pool
A modern living room with a sofa, coffee table, and lamps. A staircase is visible in the background.

6. 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.
$527 nightly
The price is $564
Oct 18 - Oct 19
Total with taxes and fees
6 Kings Ping-Pong Gazebo!
A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

7. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (288 reviews)
"Very charming hotel we really enjoyed having breakfast in the morning and ability to have a bottle of wine with dinner at Knight and our bag was very comfortable and nice having the ability to open the window and have some fresh air all in all very charming"
United States
Kathleen
$229 nightly
The price is $262
Nov 12 - Nov 13
Total with taxes and fees
The Gem Museum Suites
A green door with a window above it, a sign reading "716 - 720 Central Ave," and the number "716" on the wall.

8. 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.
$144 nightly
The price is $153
Nov 1 - Nov 2
Total with taxes and fees
Chic Studio in Downtown Highland Park near Metra
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)
"A very good property; clean, convenient, and quiet. The only thing lacking was a coffee maker in the room."
United States
Randall W.
$72 nightly
The price is $80
Oct 19 - Oct 20
Total with taxes and fees
Studio 6 Vernon Hills|ADA Queen bed,RI Shower,Nsmk|Kitchen
An outdoor patio with brick flooring, a grill, and a table with chairs.

10. 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
$71 nightly
The price is $78
Oct 19 - Oct 20
Total with taxes and fees
1 King Bed | Non-Smoking, 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.

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
$66 nightly
The price is $73
Oct 19 - Oct 20
Total with taxes and fees
Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen
A modern kitchen with white cabinetry, a central island with bar stools, a stove, oven, microwave, and a ceiling fan.

12. 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
$552 nightly
The price is $613
Oct 19 - Oct 20
Total with taxes and fees
Family Stay with Game Garage, Fire Pit, Streaming TVs and Private Yard
A hotel room with two beds, a framed picture on the wall, and a nightstand with a lamp.

13. 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
$76 nightly
The price is $85
Oct 19 - Oct 20
Total with taxes and fees
Spacious 2 Queen Beds,Nsmk|Kitchen|Studio 6 Vernon Hills
A bedroom with a large bed, two bedside tables, and decorative wall mirrors.

14. 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.
$353 nightly
The price is $393
Nov 1 - Nov 2
Total with taxes and fees
3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi
Welcome home! Enjoy the charming entrance that sets the tone for your stay.

15. Accessible Suite | Kitchen, Free Breakfast & Pool

Accessible Suite | Kitchen, Free Breakfast & Pool
Glenview
$200 nightly
The price is $224
Nov 1 - Nov 2
Total with taxes and fees
Accessible Suite | Kitchen, Free Breakfast & Pool
A building with a stone facade and a large window displaying the text 'LAUNDRY MAT'.

16. 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
$72 nightly
The price is $82
Oct 18 - Oct 19
Total with taxes and fees
King Bed Non-Smoking
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)
"We enjoyed our stay, just had a few issues with air conditioning, but host was able to get it fixed quickly."
United States
Gregory S.
$500 nightly
The price is $530
Nov 3 - Nov 4
Total with taxes and fees
Modern 3-bedroom house in tranquil North Chicago near Great Lakes Navy Base
A two-story house with a stone chimney, a front porch with steps, and a flag.

18. Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base
Mundelein
9.8 out of 10, Exceptional, (76 reviews)
"We had a great stay! The area was peaceful and felt safe. "
United States
Yoselin V.
$334 nightly
The price is $354
Oct 25 - Oct 26
Total with taxes and fees
Quaint Bungalow, near Great Lakes Naval Base
A bedroom with a bed, a ceiling fan, a radiator, a window with blinds, and a potted plant.

19. 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.
$239 nightly
The price is $263
Oct 25 - Oct 26
Total with taxes and fees
Spacious 2BR Close to it All - Chic Apt in Skokie
Room

20. Great 6 bedroom home near Chicago still avoiding the traffic of the big city

Great 6 bedroom home near Chicago still avoiding the traffic of the big city
Des Plaines
$558 nightly
The price is $597
Oct 26 - Oct 27
Total with taxes and fees
Great 6 bedroom home near Chicago still avoiding the traffic of the big city
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

Super 8 by Wyndham Chicago O'Hare Airport

Super 8 by Wyndham Chicago O'Hare Airport

8/10 Good
"Nice"
Claire 1-night trip
Posted 7 hours ago
Super 8 by Wyndham Chicago O'Hare Airport

Find out more about Highwood

Everything you need to know about Highwood vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Highwood vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Highwood vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Highwood vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Highwood. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Highwood in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $82 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Highwood rentals

At Expedia, we put the best Highwood vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Highwood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Highwood vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Highwood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.