Highwood Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • 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 holiday rentals

Nice 1BR Spot, Unwind & Relax

Nice 1BR Spot, Unwind & Relax
Lincoln Square
9.8 out of 10, Exceptional, (29 reviews)
"Very clean & cozy! Conveniently located by great shopping & restaurants!"
United States
SHERI C.
The price is NZ$334
includes taxes & fees
30 Mar - 31 Mar
Nice 1BR Spot, Unwind & Relax

Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base
Mundelein
9.8 out of 10, Exceptional, (69 reviews)
"We had a great stay! The area was peaceful and felt safe. "
United States
Yoselin V.
The price is NZ$568
includes taxes & fees
30 Mar - 31 Mar
Quaint Bungalow, near Great Lakes Naval Base

Pet-Friendly 1BR Oasis Near Chicago Downtown

Pet-Friendly 1BR Oasis Near Chicago Downtown
Lincolnwood
The price is NZ$335
includes taxes & fees
30 Mar - 31 Mar
Pet-Friendly 1BR Oasis Near Chicago Downtown

Navy Family home -Near Lake 4BR Hot Tub

Navy Family home -Near Lake 4BR Hot Tub
Gages Lake
10.0 out of 10, Exceptional, (6 reviews)
"The property was beautiful and relaxing. Our host was wonderful and responded quickly to any questions we had. "
United States
Danielle S.
The price is NZ$806
includes taxes & fees
30 Mar - 31 Mar
Navy Family home -Near Lake 4BR Hot Tub

Uptown Studio Gem Sum

Uptown Studio Gem Sum
Uptown
7.4 out of 10, Good, (6 reviews)
"The neighborhood was perfect for me. I’d like to book the same property again because of the location.The only problem was checking in. The address was wrong and if I wasn’t raised in that part of Chicago I would have been very confused.Plus I checked in late at night. It wasn’t an easy process. Next time it will be diffeeent."
United States
Darryl C.
The price is NZ$341
includes taxes & fees
30 Mar - 31 Mar
Uptown Studio Gem Sum

2-bedroom apartment just 2 minutes drive to Wrigley Field

2-bedroom apartment just 2 minutes drive to Wrigley Field
North Center
9.6 out of 10, Exceptional, (65 reviews)
"Great host, quick communication, and wonderful place to stay in Chicago. Well thought out and made our stay enjoyable. Highly recommend, we will book it again next time we are in Chicago. "
United States
Justin P.
The price is NZ$571
includes taxes & fees
31 Mar - 1 Apr
2-bedroom apartment just 2 minutes drive to Wrigley Field

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$411
includes taxes & fees
30 Mar - 31 Mar
Cute & Cozy, 1bd Condo Apartment/townhouse

Pine Beam Sloth Apartment next to Blue Line

Pine Beam Sloth Apartment next to Blue Line
Irving Park
10.0 out of 10, Exceptional, (6 reviews)
"Beautifully decorated, spotless unit. Conveniently located."
United States
Holly G.
The price is NZ$431
includes taxes & fees
30 Mar - 31 Mar
Pine Beam Sloth Apartment next to Blue Line

Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.4 out of 10, Exceptional, (66 reviews)
"Great stay i loved it"
United States
Cedes W.
The price is NZ$258
includes taxes & fees
31 Mar - 1 Apr
Cozy studio in Andersonville Chicago

1BR Apartment in Chicago

1BR Apartment in Chicago
North Center
9.0 out of 10, Wonderful, (17 reviews)
"Very clean and the host was easy to work with. "
United States
Scott S.
The price is NZ$348
includes taxes & fees
30 Mar - 31 Mar
1BR Apartment in Chicago

Chic 2BR Haven Near Irving Park

Chic 2BR Haven Near Irving Park
Irving Park
9.8 out of 10, Exceptional, (10 reviews)
"Ample accommodations for two adults. Clean and in great condition!"
United States
Kathy D.
The price is NZ$401
includes taxes & fees
31 Mar - 1 Apr
Chic 2BR Haven Near Irving Park

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$438
includes taxes & fees
4 Apr - 5 Apr
Just remodeled apartment close to airport and mall

Cozy 2BR Apartment w/ Washer & Dryer

Cozy 2BR Apartment w/ Washer & Dryer
Portage Park
The price is NZ$414
includes taxes & fees
1 Apr - 2 Apr
Cozy 2BR Apartment w/ Washer & Dryer

Bright Garden Studio

Bright Garden Studio
South Evanston
8.4 out of 10, Very good, (32 reviews)
"Great spot. Very convenient and everything we needed for a long weekend visit to Evanston."
United States
William B.
The price is NZ$419
includes taxes & fees
30 Mar - 31 Mar
Bright Garden Studio

Tiny Home Retreat with hot tub

Tiny Home Retreat with hot tub
Lake Villa
9.0 out of 10, Wonderful, (4 reviews)
"Amazing stay, great host! "
United States
Aaron L.
The price is NZ$579
includes taxes & fees
30 Mar - 31 Mar
Tiny Home Retreat with hot tub

1BR/1BA City Comfort

1BR/1BA City Comfort
Lincoln Square
7.2 out of 10, Good, (7 reviews)
"Disorganized and an experience full of avoidable issues. "
United States
Hilary A.
1BR/1BA City Comfort

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$401
includes taxes & fees
30 Mar - 31 Mar
2BR Cozy & Functional Unit

Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (78 reviews)
"Great stay. Even got to see deer on our last day. Thank you"
United States
Victoria D.
The price is NZ$338
includes taxes & fees
6 Apr - 7 Apr
Master qtr close to nature & easy urban facilities

Hot Tub Retreats

Hot Tub Retreats
Lake Villa
The price is NZ$494
includes taxes & fees
30 Mar - 31 Mar
Hot Tub Retreats

Cozy & Serene 1BR Escape

Cozy & Serene 1BR Escape
Arlington Heights
7.6 out of 10, Good, (8 reviews)
"Comfortable stay; great communication"
United States
Alyssa
The price is NZ$338
includes taxes & fees
30 Mar - 31 Mar
Cozy & Serene 1BR Escape
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.
Save an average of 15% on thousands of hotels when you're signed in

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?

Beach Park Estate: Chef's Kitchen, Nature, Fitness Room, Naval Base, Beach, Lake: This holiday home rental outside of Highwood offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 9 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a garden.

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.