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Highwood Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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.
$170 nightly
The price is $180
Sep 27 - Sep 28
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, (87 reviews)
"Great spot, safe, clean, and beautiful environment would highly recommend!"
United States
Chris F.
$196 nightly
The price is $208
Sep 30 - Oct 1
Total with taxes and fees
Master qtr close to nature & easy urban facilities
A green door with a window above it, a sign reading "716 - 720 Central Ave," and the number "716" on the wall.

3. 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 27 - Sep 28
Total with taxes and fees
Chic Studio in Downtown Highland Park near Metra
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
$164 nightly
The price is $174
Oct 5 - Oct 6
Total with taxes and fees
Chic Studio - In Downtown Highland Park, by 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
$87 nightly
The price is $96
Oct 4 - Oct 5
Total with taxes and fees
1 King Bed | Non-Smoking, Kitchen
A two-story building with a brick facade and a blue upper section.

6. 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
$219 nightly
The price is $241
Sep 27 - Sep 28
Total with taxes and fees
The Beach Park Retreat
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
$73 nightly
The price is $83
Sep 28 - Sep 29
Total with taxes and fees
King Bed Non-Smoking

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

Cozy Studio w/ Breakfast | Business Center & Pool
Glenview
$199 nightly
The price is $223
Sep 27 - Sep 28
Total with taxes and fees
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.

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
$89 nightly
The price is $98
Oct 4 - Oct 5
Total with taxes and fees
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.

10. 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
$83 nightly
The price is $92
Oct 4 - Oct 5
Total with taxes and fees
Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen
A two-story house with a stone chimney, a front porch with steps, and a flag.

11. 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.
$320 nightly
The price is $339
Sep 29 - Sep 30
Total with taxes and fees
Quaint Bungalow, near Great Lakes Naval Base
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
$93 nightly
The price is $103
Oct 4 - Oct 5
Total with taxes and fees
Spacious 2 Queen Beds,Nsmk|Kitchen|Studio 6 Vernon Hills
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.

13. 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
$83 nightly
The price is $92
Oct 4 - Oct 5
Total with taxes and fees
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.

14. 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.
$569 nightly
The price is $608
Sep 27 - Sep 28
Total with taxes and fees
6 Kings Ping-Pong Gazebo!
A patio area with outdoor seating and solar-powered lights.

15. 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.
$236 nightly
The price is $268
Sep 27 - Sep 28
Total with taxes and fees
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
A bedroom with a large bed, two bedside tables, and decorative wall mirrors.

16. 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, (28 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.
$358 nightly
The price is $398
Sep 28 - Sep 29
Total with taxes and fees
3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi
A modern living room with a sofa, a coffee table, a TV on a stand, a lamp, and a potted plant.

17. Skokie 1BR Stay Near Parks, Dining & Transit

Skokie 1BR Stay Near Parks, Dining & Transit
Skokie
$238 nightly
The price is $255
Sep 27 - Sep 28
Total with taxes and fees
Skokie 1BR Stay Near Parks, Dining & Transit
A modern kitchen with white cabinetry, a central island, and a microwave above the stove.

18. Luxury King Bed • Remodeled Safe Chicago Condo

Luxury King Bed • Remodeled Safe Chicago Condo
O'Hare
10.0 out of 10, Exceptional, (1 review)
"great place and location!"
United States
Lauren
$324 nightly
The price is $383
Sep 28 - Sep 29
Total with taxes and fees
Luxury King Bed • Remodeled Safe Chicago Condo
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.
$236 nightly
The price is $268
Sep 29 - Sep 30
Total with taxes and fees
Sunny Work From Home Apt: Near Northwestern-Chicago-Beaches-Loyola

20. 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.
$528 nightly
The price is $560
Sep 29 - Sep 30
Total with taxes and fees
Modern 3-bedroom house in tranquil North Chicago near Great Lakes Navy Base
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

Sheraton Suites Chicago O'Hare

Sheraton Suites Chicago O'Hare

10/10 Excellent
"They stole a belt from my suitcase but besides that everything seemed fine."
Jesus 1-night trip
Posted 4 hours ago
Sheraton Suites Chicago O'Hare

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 $83 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?

Pleasant 3-bedroom house with occupied basement separate entrance.: This vacation home rental near 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 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.