Highwood Vacation Rentals from CA $136: Short-Term Rentals for 2026

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Our top choices for Highwood vacation rentals

A modern living room with a grey sofa, a blue armchair, and a dining area with a table and chairs.

1. Greenwood Loft & Rooftop

Waukegan

CA $340 total

includes taxes & fees

Sep 13 - Sep 14

A modern living room with a flat-screen TV, a coffee table, a blue armchair, and a gray sofa.

2. The Beach Park Retreat

Beach Park

CA $354 total

includes taxes & fees

Sep 8 - Sep 9

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

Highland Park

Deborah

CA $234 total

includes taxes & fees

Sep 27 - Sep 28

A modern house with a covered porch, large windows, and a well-maintained garden with various plants and flowers.

4. Master qtr close to nature & easy urban facilities

Riverwoods

Suzanne H.

CA $300 total

includes taxes & fees

Sep 13 - Sep 14

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.

5. Stunning & Stylish Downtown Studio - Highland Park

Highland Park

Tom B.

CA $256 total

includes taxes & fees

Sep 27 - Sep 28

A green door with a window above it, a sign reading "716 - 720 Central Ave," and the number "716" on the wall.

6. Chic Studio in Downtown Highland Park near Metra

Highland Park

Jason H.

CA $226 total

includes taxes & fees

Sep 22 - Sep 23

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.

7. Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen

Chicago

Anonymous traveller

CA $140 total

includes taxes & fees

Sep 30 - Oct 1

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

Glenview

CA $296 total

includes taxes & fees

Sep 7 - Sep 8

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Top Highwood Hotel Reviews

Loews Chicago O'Hare Hotel

10/10 Excellent

"We stayed at the Loews while we were in town for the AUSL Softball All-Star Cup and had such a great experience! Such a nice hotel and a great location, especially if you’re going to anything in the Rosemont area. I feel terrible that I can’t remember the name of the girl who helped us at the front desk, but she was SO sweet! I mentioned we were there celebrating my 37th birthday, and she surprised us by upgrading us to a king suite. It was completely unexpected and such a kind gesture that made the weekend feel even more special! The hotel was beautiful, clean. The beds were really comfortable comfortable, and having free parking in the connected parking garage was a huge plus. We didn’t get a chance to try the restaurant, but it looked really nice! We had such a great stay and would absolutely stay here again. Highly recommend if you’re coming to Rosemont!"

Hyatt Place Chicago/O'Hare Airport

10/10 Excellent

"The room was a little dated and needing minor repairs. It was spacious and the beds were comfortable. Very surprised on how quiet the room was being next to the highway and the amount of planes flying over. Great location to the airport and Allstate arena (practically share a parking lot). Pool was nice and kids had it to themselves. Plenty of food choices nearby and easy shipt and uber eats delivery. I would stay again if I had another early flight out."

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

10/10 Excellent

"I had a wonderful stay at the Crowne Plaza Chicago. The hotel was clean, comfortable, and well-maintained, and the staff were friendly, welcoming, and helpful throughout my visit. The room was spacious and comfortable, with everything I needed for a relaxing stay."

Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

8/10 Good

"Staff were super great and helpful, did a great job at accomadting my requests and great at giving directions. Breakfast is also amazing being included and solid options The only let down is the water tastes very much of mildew but you can avoid this"

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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Highwood vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Highwood vacation rentals we have selected for you start as low as CA $136 per night. Entering your travel dates in the search wizard 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.

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?

Modern 2-Bedroom House with Free Parking and Convenient Location,: This vacation home rental near Highwood is equipped with a garden, air-conditioning, and free WiFi to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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.

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Check prices for these dates

Our top choices for Highwood vacation rentals

1. Greenwood Loft & Rooftop

2. The Beach Park Retreat

3. Chic Studio - In Downtown Highland Park, by Metra

4. Master qtr close to nature & easy urban facilities

5. Stunning & Stylish Downtown Studio - Highland Park

6. Chic Studio in Downtown Highland Park near Metra

7. Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen

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

9. Studio | Free Breakfast! Heated Indoor Pool

10. 1 Bedroom | Free Breakfast, Indoor Pool Access

11. Studio 6 Vernon Hills|ADA Queen bed,RI Shower,Nsmk|Kitchen

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

13. King Bed Non-Smoking

14. 1 King Bed | Non-Smoking, Kitchen

15. The Rooftop - Haven!

16. The Gem Museum Suites

17. Quaint Bungalow, near Great Lakes Naval Base

18. 1 King Bed | Non-Smoking, Kitchen, Shower

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

20. Accessible Suite | Kitchen, Free Breakfast & Pool

Find vacation rentals that suit your style

Top Highwood Hotel Reviews

Loews Chicago O'Hare Hotel

Marriott Chicago O'Hare

Hyatt Place Chicago/O'Hare Airport

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

Embassy Suites by Hilton Chicago O'Hare Rosemont

Holiday Inn Chicago North-Evanston by IHG

Hilton Chicago O'Hare Airport

Quality Inn O'Hare Airport

Find out more about Highwood

Frequently asked questions

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