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Highwood Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Highwood vacation rentals

Breakfast, lunch and dinner served

1. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (226 reviews)
"Great location and newly remodeled, clean rooms."
United States
Brian
The price is ￥25,816
￥29,555 total
includes taxes & fees
Aug 30 - Aug 31
The Gem Museum Suites
1 bedroom, iron/ironing board, WiFi (free), bed sheets

2. 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 ￥13,379
￥26,839 total
includes taxes & fees
Sep 13 - Sep 14
Chic Studio - In Downtown Highland Park, by Metra
Exterior detail

3. 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 ￥17,067
￥33,288 total
includes taxes & fees
Sep 7 - Sep 8
Master qtr close to nature & easy urban facilities
Living area

4. 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.
6 Kings Ping-Pong Gazebo!
Interior

5. 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 ￥13,386
￥28,543 total
includes taxes & fees
Sep 27 - Sep 28
Stunning & Stylish Downtown Studio - Highland Park
Exterior detail

6. 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 ￥10,990
￥25,151 total
includes taxes & fees
Aug 31 - Sep 1
Chic Studio in Downtown Highland Park near Metra
1 bedroom

7. 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
The price is ￥14,871
￥16,452 total
includes taxes & fees
Sep 6 - Sep 7
Studio 6 Vernon Hills|ADA Queen bed,RI Shower,Nsmk|Kitchen
Exterior

8. 1 Bedroom | Free Breakfast, Indoor Pool Access

1 Bedroom | Free Breakfast, Indoor Pool Access
Half Day
The price is ￥28,525
￥35,664 total
includes taxes & fees
Sep 27 - Sep 28
1 Bedroom | Free Breakfast, Indoor Pool Access
Exterior

9. Studio | Free Breakfast! Heated Indoor Pool

Studio | Free Breakfast! Heated Indoor Pool
Glenview
The price is ￥22,139
￥28,346 total
includes taxes & fees
Aug 31 - Sep 1
Studio | Free Breakfast! Heated Indoor Pool
Exterior

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

Cozy Studio w/ Breakfast | Business Center & Pool
Glenview
The price is ￥25,324
￥31,934 total
includes taxes & fees
Aug 31 - Sep 1
Cozy Studio w/ Breakfast | Business Center & Pool
Exterior detail

11. 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
The price is ￥13,143
￥15,723 total
includes taxes & fees
Aug 31 - Sep 1
King Bed Non-Smoking
Coffee/tea maker, fridge, microwave, oven

12. Family Stay with Game Garage, Fire Pit, Streaming TVs and Private Yard

Family Stay with Game Garage, Fire Pit, Streaming TVs and Private Yard
Libertyville
The price is ￥24,687
￥102,006 total
includes taxes & fees
Aug 30 - Aug 31
Family Stay with Game Garage, Fire Pit, Streaming TVs and Private Yard
Interior

13. 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 ￥39,043
￥95,592 total
includes taxes & fees
Sep 1 - Sep 2
Modern 3-bedroom house in tranquil North Chicago near Great Lakes Navy Base
Dining

14. "Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Downtown Evanston
10.0 out of 10, Exceptional, (17 reviews)
"Great spot to stay in Evanston, definitely recommend!"
United States
Surath G.
The price is ￥33,765
￥66,549 total
includes taxes & fees
Aug 31 - Sep 1
"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
1 bedroom

15. 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
The price is ￥14,871
￥16,452 total
includes taxes & fees
Sep 6 - Sep 7
Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen
1 bedroom

16. 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
The price is ￥16,538
￥18,298 total
includes taxes & fees
Sep 6 - Sep 7
Spacious 2 Queen Beds,Nsmk|Kitchen|Studio 6 Vernon Hills
Outdoor dining

17. 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
The price is ￥15,842
￥17,527 total
includes taxes & fees
Sep 6 - Sep 7
1 King Bed | Non-Smoking, Kitchen
Exterior detail

18. 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 ￥21,501
￥56,883 total
includes taxes & fees
Sep 12 - Sep 13
Quaint Bungalow, near Great Lakes Naval Base
Interior

19. 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 ￥26,454
￥55,748 total
includes taxes & fees
Sep 8 - Sep 9
Cozy Home by O'Hare + EV Plug
Dining

20. Haus Of Hues: MDRN Bright Peaceful Private Apt

Haus Of Hues: MDRN Bright Peaceful Private Apt
South Evanston
9.6 out of 10, Exceptional, (25 reviews)
"This stay was exactly as listed. Very cute apartment and great location!"
United States
Bradie R.
The price is ￥39,276
￥82,027 total
includes taxes & fees
Aug 31 - Sep 1
Haus Of Hues: MDRN Bright Peaceful Private Apt
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

Loews Chicago O'Hare Hotel

Loews Chicago O'Hare Hotel

10/10 Excellent
"Loews OHare is a luxury stay without the added costs that sometimes are associated with luxury, yet has all of the luxurious amenities prized by a traveler. Consistency, convenience, outstanding staff and service, absolute cleanliness, with great food choices 12 steps away from the main entry with always a safe, peaceful night’s rest. This is why I choose the Loews brand of hotels. It’s easy!"
Jason 1-night trip
Posted 7 hours ago
Loews Chicago O'Hare Hotel

Find out more about Highwood

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Look no further and take a look at our great range of rental properties in Highwood!

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.