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Highwood Holiday Rentals

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Our top choices for Highwood holiday rentals

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.
The price is NZ$317
includes taxes & fees
22 Sept - 23 Sept
Stunning & Stylish Downtown Studio - Highland Park

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.
The price is NZ$341
includes taxes & fees
8 Sept - 9 Sept
Master qtr close to nature & easy urban facilities

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 traveller
The price is NZ$173
includes taxes & fees
6 Sept - 7 Sept
Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen

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
The price is NZ$265
includes taxes & fees
13 Sept - 14 Sept
Chic Studio - In Downtown Highland Park, by Metra

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.
The price is NZ$274
includes taxes & fees
13 Sept - 14 Sept
Chic Studio in Downtown Highland Park near Metra

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

Cozy Studio w/ Breakfast | Business Center & Pool
Glenview
The price is NZ$320
includes taxes & fees
31 Aug - 1 Sept
Cozy Studio w/ Breakfast | Business Center & Pool

7. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (224 reviews)
"Great location and newly remodeled, clean rooms."
United States
Brian
The price is NZ$311
includes taxes & fees
30 Aug - 31 Aug
The Gem Museum Suites

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.
The price is NZ$1,121
includes taxes & fees
1 Sept - 2 Sept
6 Kings Ping-Pong Gazebo!

9. Studio | Free Breakfast! Heated Indoor Pool

Studio | Free Breakfast! Heated Indoor Pool
Glenview
The price is NZ$286
includes taxes & fees
30 Aug - 31 Aug
Studio | Free Breakfast! Heated Indoor Pool

10. 1 Bedroom | Free Breakfast, Indoor Pool Access

1 Bedroom | Free Breakfast, Indoor Pool Access
Half Day
The price is NZ$366
includes taxes & fees
24 Sept - 25 Sept
1 Bedroom | Free Breakfast, Indoor Pool Access

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 traveller
The price is NZ$193
includes taxes & fees
23 Sept - 24 Sept
Spacious 2 Queen Beds,Nsmk|Kitchen|Studio 6 Vernon Hills

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 traveller
The price is NZ$183
includes taxes & fees
30 Aug - 31 Aug
1 King Bed | Non-Smoking, Kitchen

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 traveller
The price is NZ$165
includes taxes & fees
7 Sept - 8 Sept
King Bed Non-Smoking

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 traveller
The price is NZ$173
includes taxes & fees
23 Sept - 24 Sept
Studio 6 Vernon Hills|ADA Queen bed,RI Shower,Nsmk|Kitchen

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.
The price is NZ$580
includes taxes & fees
12 Sept - 13 Sept
Quaint Bungalow, near Great Lakes Naval Base

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 traveller
The price is NZ$181
includes taxes & fees
23 Sept - 24 Sept
1 King Bed | Non-Smoking, Kitchen, Shower

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.
The price is NZ$552
includes taxes & fees
9 Sept - 10 Sept
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.
The price is NZ$1,009
includes taxes & fees
8 Sept - 9 Sept
Modern 3-bedroom house in tranquil North Chicago near Great Lakes Navy Base

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.
The price is NZ$466
includes taxes & fees
31 Aug - 1 Sept
Sunny Work From Home Apt: Near Northwestern-Chicago-Beaches-Loyola

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.
The price is NZ$438
includes taxes & fees
9 Sept - 10 Sept
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

Find out more about Highwood

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Highwood holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Highwood. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Highwood. Seeing all the best attractions is bound to make you fall in love with Highwood. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Highwood short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Highwood?

Yes, we offer holiday rentals where you'll be just 12.7 mi (20.4 km) from Six Flags Great America, providing a more secluded option if you want peace and quiet. Highwood is known for its shopping and restaurants.

What are some of the best holiday rentals that Highwood has to offer?

Vintage Escape 1BR Two Blocks Away From Beach: This holiday home rental outside of 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 wider area, you’ll find Lake Forest College and Ravinia Pavilion.

What are holiday rentals like in Highwood?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Highwood. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll have everything you want. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for a family trip.