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Highwood Vacation Rentals

Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

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
Aug 25 - Aug 26
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, (86 reviews)
"Lovely, quiet property with easy access to retail & restaurants. Perfect for a long weekend away."
United States
Suzanne H.
$203 nightly
The price is $215
Aug 25 - Aug 26
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. Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen

Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen
Chicago
10.0 out of 10, Exceptional, (16 reviews)
"Great place to stay"
United States
Anonymous traveler
$94 nightly
The price is $104
Aug 25 - Aug 26
Total with taxes and fees
Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen
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
$154 nightly
The price is $163
Sep 13 - Sep 14
Total with taxes and fees
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.

5. 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.
$154 nightly
The price is $163
Sep 13 - Sep 14
Total with taxes and fees
Chic Studio in Downtown Highland Park near Metra

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

Cozy Studio w/ Breakfast | Business Center & Pool
Glenview
$171 nightly
The price is $192
Aug 30 - Aug 31
Total with taxes and fees
Cozy Studio w/ Breakfast | Business Center & Pool
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, (221 reviews)
"Great location and newly remodeled, clean rooms."
United States
Brian
$178 nightly
The price is $204
Aug 25 - Aug 26
Total with taxes and fees
The Gem Museum Suites
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.
$610 nightly
The price is $652
Aug 25 - Aug 26
Total with taxes and fees
6 Kings Ping-Pong Gazebo!

9. Studio | Free Breakfast! Heated Indoor Pool

Studio | Free Breakfast! Heated Indoor Pool
Glenview
$153 nightly
The price is $171
Aug 30 - Aug 31
Total with taxes and fees
Studio | Free Breakfast! Heated Indoor Pool
A large, two-story building with a stone facade, a prominent entrance with a glass door, and a landscaped garden with flowering plants.

10. 1 Bedroom | Free Breakfast, Indoor Pool Access

1 Bedroom | Free Breakfast, Indoor Pool Access
Half Day
$180 nightly
The price is $200
Sep 7 - Sep 8
Total with taxes and fees
1 Bedroom | Free Breakfast, Indoor Pool Access
A hotel room with two beds, a framed picture on the wall, and a nightstand with a lamp.

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

Spacious 2 Queen Beds,Nsmk|Kitchen|Studio 6 Vernon Hills
Chicago
9.4 out of 10, Exceptional, (21 reviews)
"Good place to stay,,"
United States
Anonymous traveler
$104 nightly
The price is $115
Aug 25 - Aug 26
Total with taxes and fees
Spacious 2 Queen Beds,Nsmk|Kitchen|Studio 6 Vernon Hills
An outdoor patio with brick flooring, a grill, and a table with chairs.

12. 1 King Bed | Non-Smoking, Kitchen

1 King Bed | Non-Smoking, Kitchen
Chicago
10.0 out of 10, Exceptional, (14 reviews)
"Everything nice neat and clean"
United States
Anonymous traveler
$98 nightly
The price is $108
Aug 25 - Aug 26
Total with taxes and fees
1 King Bed | Non-Smoking, Kitchen
A building with a stone facade and a large window displaying the text 'LAUNDRY MAT'.

13. 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
$87 nightly
The price is $99
Aug 25 - Aug 26
Total with taxes and fees
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.

14. 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
$94 nightly
The price is $104
Sep 6 - Sep 7
Total with taxes and fees
Studio 6 Vernon Hills|ADA Queen bed,RI Shower,Nsmk|Kitchen
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, (74 reviews)
"Fantastic location. Very clean. Great/quick communication with host. Definitely recommend!"
United States
Jaclyn Z.
$337 nightly
The price is $357
Sep 8 - Sep 9
Total with taxes and fees
Quaint Bungalow, near Great Lakes Naval Base
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.

16. 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
$94 nightly
The price is $104
Aug 30 - Aug 31
Total with taxes and fees
1 King Bed | Non-Smoking, Kitchen, Shower
A staircase with a wooden finish and black railings, leading to a room with a large wooden door and a white ceiling.

17. Cozy Home by O'Hare + EV Plug

Cozy Home by O'Hare + EV Plug
Des Plaines
9.8 out of 10, Exceptional, (21 reviews)
"Beautiful, unique, and clean place to stay. Comfortable beds, quiet, and plenty of space. Great place to stay."
United States
Richie S.
$343 nightly
The price is $367
Sep 1 - Sep 2
Total with taxes and fees
Cozy Home by O'Hare + EV Plug

18. 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.
$575 nightly
The price is $609
Sep 8 - Sep 9
Total with taxes and fees
Modern 3-bedroom house in tranquil North Chicago near Great Lakes Navy Base
An outdoor patio area with a wooden fence, outdoor seating with chairs and a table, and multiple ground lamps.

19. 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.
$247 nightly
The price is $281
Aug 31 - Sep 1
Total with taxes and fees
Sunny Work From Home Apt: Near Northwestern-Chicago-Beaches-Loyola
A patio area with outdoor seating and solar-powered lights.

20. 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.
$229 nightly
The price is $260
Sep 23 - Sep 24
Total with taxes and fees
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
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

SpringHill Suites Chicago O'Hare by Marriott

SpringHill Suites Chicago O'Hare by Marriott

10/10 Excellent
"Great place to stay. Awesome breakfast every day, nice pool, Good location for easy accessibility to get to Chicago"
Kristina 2-night trip
Posted less than an hour ago
SpringHill Suites Chicago O'Hare by Marriott

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 $156 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?

Vintage Escape 1BR Two Blocks Away From Beach: This vacation home rental near Highwood is equipped with a garden, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop, and an electric kettle.

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 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.