Highwood Vacation Rentals

  • 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
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Highwood vacation rentals

Property grounds

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
North Center
9.6 out of 10, Exceptional, (75 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is ￥25,354
￥58,009 total
includes taxes & fees
May 31 - Jun 1
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
Iron/ironing board, travel crib, WiFi, bed sheets

Comfy Studio in Portage Park- Great Value!

Comfy Studio in Portage Park- Great Value!
Portage Park
10.0 out of 10, Exceptional, (1 review)
"The host was very friendly, helpful, and communicative. The apartment was clean and quiet. "
United States
Clifton C.
The price is ￥12,263
￥27,851 total
includes taxes & fees
Jun 3 - Jun 4
Comfy Studio in Portage Park- Great Value!
Terrace/patio

Historic Coach House in Evanston One Block to Beach and Close to Town and NU!

Historic Coach House in Evanston One Block to Beach and Close to Town and NU!
South Evanston
10.0 out of 10, Exceptional, (38 reviews)
"Excellent property and host. Truly enjoyed our stay. "
United States
Shashi Y.
The price is ￥31,742
￥53,097 total
includes taxes & fees
Jun 2 - Jun 3
Historic Coach House in Evanston One Block to Beach and Close to Town and NU!
TV, offices

1BR/1BA City Comfort

1BR/1BA City Comfort
Lincoln Square
7.8 out of 10, Good, (9 reviews)
"Great location, very clean. Easy check in and check out. Great communication."
United States
Thomas L.
The price is ￥15,767
￥33,548 total
includes taxes & fees
Jun 8 - Jun 9
1BR/1BA City Comfort
TV, offices

Cozy 1-Bedroom Apartment

Cozy 1-Bedroom Apartment
Portage Park
10.0 out of 10, Exceptional, (1 review)
"The place was great! It's stocked with the basics, bed and couch are comfy, and everything is clean. There were only a handful of times when I heard the upstairs neighbor, but nothing too crazy. The neighborhood itself is very cute and quiet, with good food and stores within walking distance. Street parking was easy. Thank you! "
United States
Sarah M.
The price is ￥13,856
￥31,309 total
includes taxes & fees
Jun 2 - Jun 3
Cozy 1-Bedroom Apartment
Iron/ironing board, travel crib, WiFi, bed sheets

Trendy & Comfy Studio Unit

Trendy & Comfy Studio Unit
Portage Park
9.2 out of 10, Wonderful, (7 reviews)
"It was really a great place. Bb oo"
United States
Kate S.
The price is ￥14,356
￥30,325 total
includes taxes & fees
Jun 1 - Jun 2
Trendy & Comfy Studio Unit
TV, offices

Chic, Quiet 1BR Near Dining Options– Perfect for 2

Chic, Quiet 1BR Near Dining Options– Perfect for 2
Avondale
7.4 out of 10, Good, (3 reviews)
"It was a very nice place for either one or two guests to stay. The video on the lock box was very helpful. Make sure guests know it takes about 10 minutes for the hot water to warm up. I knew that in advance, so it was no problem."
United States
ronald b.
The price is ￥13,696
￥31,122 total
includes taxes & fees
Jun 8 - Jun 9
Chic, Quiet 1BR Near Dining Options– Perfect for 2
2 bedrooms, iron/ironing board, travel crib, WiFi

Well-Equipped 2BR Unit with Parking

Well-Equipped 2BR Unit with Parking
North Evanston
10.0 out of 10, Exceptional, (4 reviews)
"Great place. Super clean and easy off street parking. Thanks !"
United States
Ann N.
The price is ￥19,748
￥42,236 total
includes taxes & fees
Jun 3 - Jun 4
Well-Equipped 2BR Unit with Parking
TV, offices

Stylish 1BR Stay in Irving Vibes

Stylish 1BR Stay in Irving Vibes
Irving Park
8.4 out of 10, Very Good, (5 reviews)
"Great place to stay Comfy bed and setting"
United States
Steven
The price is ￥11,945
￥29,072 total
includes taxes & fees
Jun 1 - Jun 2
Stylish 1BR Stay in Irving Vibes
TV

1BR 1BA Windy City Hideout

1BR 1BA Windy City Hideout
Belmont Cragin
The price is ￥15,767
￥33,548 total
includes taxes & fees
Jun 16 - Jun 17
1BR 1BA Windy City Hideout
Terrace/patio

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)
"Everything was as described. I would stay here again."
United States
Brent S.
The price is ￥15,767
￥36,955 total
includes taxes & fees
Jun 9 - Jun 10
Sunny Work From Home Apt: Near Northwestern-Chicago-Beaches-Loyola
Paper towels

Just remodeled apartment close to airport and mall

Just remodeled apartment close to airport and mall
Elk Grove Village
10.0 out of 10, Exceptional, (16 reviews)
"Very nice place to stay in secure neighborhood "
United States
Christina F.
The price is ￥21,500
￥40,039 total
includes taxes & fees
May 31 - Jun 1
Just remodeled apartment close to airport and mall
TV

Cozy 2BR Apt for a Seamless Stay

Cozy 2BR Apt for a Seamless Stay
Portage Park
8.0 out of 10, Very Good, (1 review)
"Everything as advertised. The only part that I was unsure of was what to do with the keys as this was not stated in any of the information provided. So I left them on the table. "
United States
Michael P.
The price is ￥18,822
￥40,724 total
includes taxes & fees
Jun 1 - Jun 2
Cozy 2BR Apt for a Seamless Stay
Interior

Comfortable 2BR Chicago Apt

Comfortable 2BR Chicago Apt
Albany Park
9.4 out of 10, Exceptional, (9 reviews)
"Perfect location for our trip. Very functional and comfortable. "
United States
Michael
The price is ￥20,067
￥41,959 total
includes taxes & fees
Jun 8 - Jun 9
Comfortable 2BR Chicago Apt
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (78 reviews)
"Great stay i loved it"
United States
Cedes W.
The price is ￥12,920
￥25,786 total
includes taxes & fees
Jun 16 - Jun 17
Cozy studio in Andersonville Chicago
Exterior detail

Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (83 reviews)
"nice little place! quiet area "
United States
Nayeli A.
The price is ￥17,359
￥32,745 total
includes taxes & fees
Jun 18 - Jun 19
Master qtr close to nature & easy urban facilities
TV, offices

Perfectly Located 1-Bedroom Unit

Perfectly Located 1-Bedroom Unit
South Evanston
10.0 out of 10, Exceptional, (1 review)
"The apartment was very clean and the bed was super comfortable. We slept great. We didn’t spend much time at the apartment but for our trip it was exactly what we needed. "
United States
V S.
The price is ￥17,678
￥35,265 total
includes taxes & fees
Jun 16 - Jun 17
Perfectly Located 1-Bedroom Unit
Property grounds

Evanston Garden Guest House

Evanston Garden Guest House
North Evanston
10.0 out of 10, Exceptional, (2 reviews)
"Perfect little place in Evanston—great decor, nice location, well equipped. Communication with owners was great, I would happily stay here again."
United States
Michelle
The price is ￥20,385
￥36,249 total
includes taxes & fees
Jun 22 - Jun 23
Evanston Garden Guest House
Dining

1-Bedroom Pad | Cozy + All-Set

1-Bedroom Pad | Cozy + All-Set
West Dempster
8.0 out of 10, Very Good, (2 reviews)
"This was a great space. The location was perfect and we had everthing we needed. We would definitely stay here again. "
United States
Amanda M.
The price is ￥19,111
￥37,114 total
includes taxes & fees
Jun 9 - Jun 10
1-Bedroom Pad | Cozy + All-Set
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Highwood Hotel Reviews

Super 8 by Wyndham Chicago O'Hare Airport

Super 8 by Wyndham Chicago O'Hare Airport

6/10 Okay
"Needs to be renovated"
Victoria 1-night trip
Posted 1 hour ago
Super 8 by Wyndham Chicago O'Hare Airport

Find out more about Highwood

Search for holiday rentals in Highwood on Expedia! You can easily find your home rentals, villas, holiday apartments in Highwood using one of the methods below:

  • View our selection of featured holiday rentals in Highwood
  • Use the map to find apartments and other holiday homes in the Highwood neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Highwood while they last

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?

Breathtaking home close to Schaumburg, Chicago: This vacation home rental near Highwood offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a terrace, a garden, and a selection of games so you can immerse yourself in your vacation.

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 Naval Base Great Lakes and Lake Forest College.

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.