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Highwood Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Highwood vacation rentals

A hotel room with a bed, two pillows, a nightstand with a lamp, and two abstract paintings on the wall.

1. 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
Oct 22 - Oct 23
Total with taxes and fees
Chic Studio - In Downtown Highland Park, by Metra
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 19 - Oct 20
Total with taxes and fees
Master qtr close to nature & easy urban facilities
A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

3. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (283 reviews)
"Really helpful staff, really nice rooms."
United States
Archita
$252 nightly
The price is $288
Nov 9 - Nov 10
Total with taxes and fees
The Gem Museum Suites
An outdoor patio with brick flooring, a grill, and a table with chairs.

4. 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
$68 nightly
The price is $75
Nov 8 - Nov 9
Total with taxes and fees
1 King Bed | Non-Smoking, Kitchen
A modern living room with a sofa, coffee table, and lamps. A staircase is visible in the background.

5. 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.
$573 nightly
The price is $613
Nov 2 - Nov 3
Total with taxes and fees
6 Kings Ping-Pong Gazebo!
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.

6. 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.
$174 nightly
The price is $184
Nov 10 - Nov 11
Total with taxes and fees
Stunning & Stylish Downtown Studio - Highland Park
A green door with a window above it, a sign reading "716 - 720 Central Ave," and the number "716" on the wall.

7. 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 8 - Nov 9
Total with taxes and fees
Chic Studio in Downtown Highland Park near Metra
Welcome home! Enjoy the charming entrance that sets the tone for your stay.

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

Cozy Studio w/ Breakfast | Business Center & Pool
Glenview
$200 nightly
The price is $224
Nov 1 - Nov 2
Total with taxes and fees
Cozy Studio w/ Breakfast | Business Center & Pool
A building with a stone facade and a large window displaying the text 'LAUNDRY MAT'.

9. 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 12 - Oct 13
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.

10. 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
$70 nightly
The price is $77
Nov 8 - Nov 9
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.

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
$64 nightly
The price is $71
Nov 8 - Nov 9
Total with taxes and fees
Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen
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
$74 nightly
The price is $82
Nov 8 - Nov 9
Total with taxes and fees
Spacious 2 Queen Beds,Nsmk|Kitchen|Studio 6 Vernon Hills
A dining area with a table, chairs, a vase of flowers, and a kitchen area with a refrigerator and cabinets.

13. 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.
$228 nightly
The price is $249
Nov 8 - Nov 9
Total with taxes and fees
Well-Equipped 2BR Unit with Parking
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.
$345 nightly
The price is $384
Nov 1 - Nov 2
Total with taxes and fees
3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi
A modern interior with a dining area, seating, a fireplace, and large windows offering a view of buildings outside.

15. Chicago's Hidden Treasure "Evanston, IL" Urban Luxury with comfort

Chicago's Hidden Treasure "Evanston, IL" Urban Luxury with comfort
Downtown Evanston
10.0 out of 10, Exceptional, (37 reviews)
"Very nice place to stay with a great location. Thanks!"
United States
Robin M.
$372 nightly
The price is $422
Oct 12 - Oct 13
Total with taxes and fees
Chicago's Hidden Treasure "Evanston, IL" Urban Luxury with comfort
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.
$333 nightly
The price is $353
Oct 11 - Oct 12
Total with taxes and fees
Quaint Bungalow, near Great Lakes Naval Base
A compact kitchen with a dining area, a refrigerator, a sink, and a cabinet.

17. 1 Queen Bed | Non-Smoking, Kitchen

1 Queen Bed | Non-Smoking, Kitchen
Vernon Hills
10.0 out of 10, Exceptional, (3 reviews)
"Quick stopover spot, comfy bed helped me catch needed rest fast."
United States
Anonymous traveler
$111 nightly
The price is $123
Oct 17 - Oct 18
Total with taxes and fees
1 Queen 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.

18. 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
$64 nightly
The price is $71
Nov 8 - Nov 9
Total with taxes and fees
1 King Bed | Non-Smoking, Kitchen, Shower
Interior

19. 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.
$544 nightly
The price is $577
Nov 2 - Nov 3
Total with taxes and fees
Modern 3-bedroom house in tranquil North Chicago near Great Lakes Navy Base
A modern living room with a sofa, a blue armchair, a coffee table, and a TV mounted on the wall.

20. 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
$232 nightly
The price is $255
Oct 20 - Oct 21
Total with taxes and fees
The Beach Park Retreat
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

Quality Inn O'Hare Airport

Quality Inn O'Hare Airport

10/10 Excellent
"Great everything... Fast shuttle to and from the airport. The bar/restaurant had great affordable food and drinks. The staff was very helpful."
Sharon 1-night trip
Posted less than an hour ago
Quality Inn 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.