Highwood Vacation Rentals from CA $87: Short-Term Rentals for 2026

Q: 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.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Highwood vacation rentals

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.

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

Chicago

Anonymous traveller

CA $107 total

includes taxes & fees

Nov 19 - Nov 20

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

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

Highland Park

Deborah

CA $214 total

includes taxes & fees

Nov 30 - Dec 1

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.

3. Stunning & Stylish Downtown Studio - Highland Park

Highland Park

Tom B.

CA $215 total

includes taxes & fees

Nov 29 - Nov 30

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

Chris F.

CA $277 total

includes taxes & fees

Nov 18 - Nov 19

A room with a bed, a dining table with chairs, a potted plant, and a view of a cityscape through a window.

5. Chic Studio in Downtown Highland Park near Metra

Highland Park

Jason H.

CA $206 total

includes taxes & fees

Nov 29 - Nov 30

6. 1 King Bed | Non-Smoking, Kitchen, Shower

Chicago

Anonymous traveller

CA $107 total

includes taxes & fees

Nov 19 - Nov 20

A hotel lobby with a striped carpet, two leather armchairs, a small table with a lamp, and a large window.

7. 1 King Bed | Non-Smoking, Kitchen

Chicago

Anonymous traveller

CA $113 total

includes taxes & fees

Nov 19 - Nov 20

A hotel room with two beds, a framed picture on the wall, and a nightstand with a lamp.

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

Chicago

Will B.

CA $122 total

includes taxes & fees

Nov 19 - Nov 20

A bedroom with a bed, a chair, a desk, a bathroom with a bathtub, and a shower.

9. King Bed Non-Smoking

Chicago

Anonymous traveller

CA $106 total

includes taxes & fees

Dec 1 - Dec 2

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

Chicago

Randall W.

CA $118 total

includes taxes & fees

Dec 3 - Dec 4

A modern living room with a sofa, coffee table, and lamps. A staircase is visible in the background.

11. 6 Kings Ping-Pong Gazebo!

Northbrook

Cj Y.

CA $796 total

includes taxes & fees

Nov 9 - Nov 10

A hotel room with a bed, bedside lamps, a television, a desk, and a chair.

12. 1 Queen Bed | Non-Smoking, Kitchen

Vernon Hills

Anonymous traveller

CA $164 total

includes taxes & fees

Nov 22 - Nov 23

Welcome home! Enjoy the charming entrance that sets the tone for your stay.

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

Glenview

CA $316 total

includes taxes & fees

Nov 29 - Nov 30

A compact kitchen with white cabinets, a stove, microwave, and a coffee maker.

14. Spacious 2BR Close to it All - Chic Apt in Skokie

West Dempster

Jean W.

CA $335 total

includes taxes & fees

Nov 10 - Nov 11

A modern living room with a glass coffee table, black leather sofa, and a painting on the wall.

15. Wonderful 3-bedroom apartment in West Village, Evanston

South Evanston

CA $595 total

includes taxes & fees

Nov 9 - Nov 10

A dining area with a round table, four chairs, a chandelier, and a kitchen with white cabinets and a countertop.

16. 1-Bedroom Pad | Cozy + All-Set

West Dempster

Amanda M.

CA $250 total

includes taxes & fees

Nov 16 - Nov 17

A bathroom with a bathtub, toilet, sink, and a mirror with lights.

17. Bright & Cozy Chicago 1BR | Near Dining & Transit

West Ridge

CA $316 total

includes taxes & fees

Nov 16 - Nov 17

A two-story house with a stone chimney, a front porch with steps, and a flag.

18. Quaint Bungalow, near Great Lakes Naval Base

Mundelein

Benjamin O.

CA $474 total

includes taxes & fees

Nov 9 - Nov 10

A bathroom with a white bathtub, pink tiled walls, a window, and a black polka dot shower curtain.

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

Skokie

CA $326 total

includes taxes & fees

Nov 16 - Nov 17

A spacious lobby with a high ceiling, a reception desk, comfortable seating, and a large stained glass window.

20. The Gem Museum Suites

Downtown Evanston

Zhaohua

CA $317 total

includes taxes & fees

Dec 5 - Dec 6

View all properties

Find vacation rentals that suit your style

Top Highwood Hotel Reviews

An outdoor patio with a stone fire table, seating, and a grill.

Homewood Suites by Hilton Chicago-Lincolnshire

Lincolnshire

10/10 Excellent

JONATHON

A spacious lobby with a reception desk, seating area, and a large glass door entrance.

La Quinta Inn & Suites by Wyndham Bannockburn-Deerfield

Deerfield

10/10 Excellent

Amitpal

A spacious lobby with a fireplace, comfortable seating, and a high ceiling with multiple balconies.

Embassy Suites by Hilton Chicago North Shore Deerfield

Deerfield

10/10 Excellent

Vihaan

A modern restaurant with a bar area, a large dining table with chairs, and a fireplace.

Hampton Inn & Suites Chicago/Lincolnshire

Lincolnshire

10/10 Excellent

Benjamin

A large, symmetrical building with a central entrance, flanked by two wings, and surrounded by well-maintained lawns and hedges.

Staybridge Suites, Lincolnshire by IHG

Half Day

10/10 Excellent

Quy

A building entrance with a brick facade, a covered walkway, and trees framing the entrance.

Holiday Inn Express Chicago NW - Vernon Hills by IHG

Vernon Hills

10/10 Excellent

Jaswant

A hotel room with a large bed, an air conditioning unit, a desk with a chair, and a window with curtains.

Motel 6 Prospect Heights, IL

Prospect Heights

10/10 Excellent

Sebastien

A Holiday Inn Express & Suites building with a covered entrance, stone pillars, and a clear blue sky.

Holiday Inn Express & Suites Prospect Heights by IHG

Prospect Heights

10/10 Excellent

JOSELINO CRUZ

A two-story house with a stone chimney, a visible front door, and a well-maintained garden with a bench and a birdbath.

Staybridge Suites Chicago - Glenview by IHG

Glenview

10/10 Excellent

Anonymous traveller

A hotel with a large building, a fountain, and a pond.

Hotel Indigo Chicago-Vernon Hills by IHG

Vernon Hills

10/10 Excellent

Harshid

A compact kitchen with a dining table, a microwave, a coffee maker, and a refrigerator.

Sonesta Simply Suites Chicago Libertyville

Libertyville

10/10 Excellent

Felicia

A hotel lobby with multiple seating areas, including tables and chairs, a sofa, and a reception desk.

Hampton Inn & Suites Chicago-Libertyville

Libertyville

10/10 Excellent

Rob

A hotel room with a blue sofa, a wooden coffee table, a black leather chair, a bed with white bedding, a flat-screen TV mounted on the wall, and a large window.

Holiday Inn Express & Suites Waukegan by IHG

Waukegan

10/10 Excellent

Miguelangel

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 $87 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?

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.

Highwood Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Highwood vacation rentals

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

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

3. Stunning & Stylish Downtown Studio - Highland Park

4. Master qtr close to nature & easy urban facilities

5. Chic Studio in Downtown Highland Park near Metra

6. 1 King Bed | Non-Smoking, Kitchen, Shower

7. 1 King Bed | Non-Smoking, Kitchen

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

9. King Bed Non-Smoking

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

11. 6 Kings Ping-Pong Gazebo!

12. 1 Queen Bed | Non-Smoking, Kitchen

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

14. Spacious 2BR Close to it All - Chic Apt in Skokie

15. Wonderful 3-bedroom apartment in West Village, Evanston

16. 1-Bedroom Pad | Cozy + All-Set

17. Bright & Cozy Chicago 1BR | Near Dining & Transit

18. Quaint Bungalow, near Great Lakes Naval Base

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

20. The Gem Museum Suites

Find vacation rentals that suit your style

Top Highwood Hotel Reviews

Homewood Suites by Hilton Chicago-Lincolnshire

10/10 Excellent

Find out more about Highwood

Highwood vacation rentals: An excellent choice for every season

How to find incredible deals on Highwood rentals

Frequently Asked Questions

Are there vacation rentals in Highwood?

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

What can I see and do in Highwood?

What are vacation rentals like in Highwood?