Highwood Holiday Rentals

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Our top choices for Highwood holiday rentals

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

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
South Evanston
10.0 out of 10, Exceptional, (48 reviews)
"The place was awesome - very clean !! Great location !! "
United States
John R.
The price is NZ$407
includes taxes & fees
18 May - 19 May
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More

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, (73 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is NZ$584
includes taxes & fees
19 May - 20 May
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC

F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
Barrington
9.8 out of 10, Exceptional, (9 reviews)
"Very nice little spot... Host was absolutely wonderful!!! Definitely stay here again!"
United States
Adam B.
The price is NZ$293
includes taxes & fees
18 May - 19 May
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC

Chic Studio in Downtown Highland Park near Metra

Chic Studio in Downtown Highland Park near Metra
Highland Park
8.0 out of 10, Very good, (4 reviews)
"Nice and cozy! Easy access to the surrounding area."
United States
Jason H.
The price is NZ$298
includes taxes & fees
18 May - 19 May
Chic Studio in Downtown Highland Park near Metra

2BR Cozy & Functional Unit

2BR Cozy & Functional Unit
Belmont Cragin
10.0 out of 10, Exceptional, (1 review)
"The host was available and helpful at check-in. The 2 bedroom apartment was clean and well stocked. We felt safe and at home. We slept well. We did not notice any street noise at night. We had more than we epected and everything we needed.It might be helpful to color code the keys with nail polish or something. The three locks to get into the unit felt like a struggle because we needed a quick turn around time between events. Otherwise, it was a great stay!!"
United States
Laura V.
The price is NZ$373
includes taxes & fees
19 May - 20 May
2BR Cozy & Functional Unit

Bright Garden Studio

Bright Garden Studio
South Evanston
8.2 out of 10, Very good, (34 reviews)
"Easy access. Nice location. Available shrot notice."
United States
Drew H.
The price is NZ$460
includes taxes & fees
19 May - 20 May
Bright Garden Studio

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 NZ$335
includes taxes & fees
26 May - 27 May
Cozy 1-Bedroom Apartment

Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (82 reviews)
"Had a lovely stay in a beautiful home! The setting is very secluded and quiet."
United States
Kyle M.
The price is NZ$332
includes taxes & fees
28 May - 29 May
Master qtr close to nature & easy urban facilities

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 NZ$299
includes taxes & fees
26 May - 27 May
Comfy Studio in Portage Park- Great Value!

Evanston Garden Guest House

Evanston Garden Guest House
North Evanston
10.0 out of 10, Exceptional, (1 review)
"Very friendly and hospitable. Always available to assist. Nice place. Highly recommend."
United States
Tracey B.
The price is NZ$359
includes taxes & fees
27 May - 28 May
Evanston Garden Guest House

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, (37 reviews)
"Excellent property and host. Truly enjoyed our stay. "
United States
Shashi Y.
The price is NZ$520
includes taxes & fees
25 May - 26 May
Historic Coach House in Evanston One Block to Beach and Close to Town and NU!

Cute & Cozy, 1bd Condo Apartment/townhouse

Cute & Cozy, 1bd Condo Apartment/townhouse
Zion
10.0 out of 10, Exceptional, (2 reviews)
"The property was very clean and has a very relaxing feel to it. The owner was very responsive when I had any questions and was very helpful. "
United States
Caleb C.
The price is NZ$453
includes taxes & fees
18 May - 19 May
Cute & Cozy, 1bd Condo Apartment/townhouse

Mins from O'Hare • Safe Location • Private Parking

Mins from O'Hare • Safe Location • Private Parking
O'Hare
The price is NZ$460
includes taxes & fees
19 May - 20 May
Mins from O'Hare • Safe Location • Private Parking

Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (77 reviews)
"Great stay i loved it"
United States
Cedes W.
The price is NZ$334
includes taxes & fees
15 June - 16 June
Cozy studio in Andersonville Chicago

Bright & Cozy Chicago 1BR | Near Dining & Transit

Bright & Cozy Chicago 1BR | Near Dining & Transit
West Ridge
9.0 out of 10, Wonderful, (2 reviews)
"The place was bery nice and we enjoyed our stay."
United States
Peter T.
The price is NZ$450
includes taxes & fees
31 May - 1 June
Bright & Cozy Chicago 1BR | Near Dining & Transit

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 NZ$345
includes taxes & fees
26 May - 27 May
1BR/1BA City Comfort

Skokie 1BR Gem - Davis

Skokie 1BR Gem - Davis
3.0 star property
Skokie
Skokie 1BR Gem - Davis

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 NZ$432
includes taxes & fees
25 May - 26 May
Just remodeled apartment close to airport and mall

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 NZ$303
includes taxes & fees
26 May - 27 May
Trendy & Comfy Studio Unit

PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard

PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard
Arlington Heights
9.0 out of 10, Wonderful, (6 reviews)
"Host was very responsive. Location was perfect for what we needed.Really liked having a garage for the car."
United States
Katie C.
The price is NZ$726
includes taxes & fees
18 May - 19 May
PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard
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

Everything you need to know about Highwood holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Highwood holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Highwood holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Highwood holiday rentals we have selected for you start as low as NZ$258 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 holiday 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 holiday.

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 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?

Breathtaking home close to Schaumburg, Chicago: This holiday home rental outside of Highwood offers a fireplace, a patio and a BBQ 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 that you can cook with friends or family. It offers a terrace, a garden and a selection of games so that you can immerse yourself in your holiday.

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 wider area, you’ll find Naval Base Great Lakes and Lake Forest College.

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.