Highwood Holiday Rentals

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Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

Our top choices for Highwood holiday rentals

TV

Nice 1BR Spot, Unwind & Relax

Nice 1BR Spot, Unwind & Relax
Lincoln Square
9.8 out of 10, Exceptional, (29 reviews)
"This was a great apartment in the heart of Lincoln Square. The kitchen is fully equipped, the bed was comfortable and there are a lot of amenities and public transportation close by. I will definitely be staying hear again! "
United States
Lisa
The price is HK$642
HK$1,494 total
includes taxes & fees
30 Mar - 31 Mar
Nice 1BR Spot, Unwind & Relax
Exterior detail

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 HK$1,057
HK$2,582 total
includes taxes & fees
30 Mar - 31 Mar
Quaint Bungalow, near Great Lakes Naval Base
Living area

Pet-Friendly 1BR Oasis Near Chicago Downtown

Pet-Friendly 1BR Oasis Near Chicago Downtown
Lincolnwood
The price is HK$846
HK$1,508 total
includes taxes & fees
30 Mar - 31 Mar
Pet-Friendly 1BR Oasis Near Chicago Downtown
Fridge, microwave, oven, stovetop

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 HK$1,206
HK$3,667 total
includes taxes & fees
30 Mar - 31 Mar
Navy Family home -Near Lake 4BR Hot Tub
Iron/ironing board, WiFi

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 HK$736
HK$1,545 total
includes taxes & fees
30 Mar - 31 Mar
Uptown Studio Gem Sum
Property grounds

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 HK$1,050
HK$2,591 total
includes taxes & fees
30 Mar - 31 Mar
2-bedroom apartment just 2 minutes drive to Wrigley Field
Smart TV

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 HK$737
HK$1,802 total
includes taxes & fees
30 Mar - 31 Mar
Cute & Cozy, 1bd Condo Apartment/townhouse
Interior

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 HK$885
HK$1,931 total
includes taxes & fees
30 Mar - 31 Mar
Pine Beam Sloth Apartment next to Blue Line
1 bedroom, iron/ironing board, free WiFi, bed sheets

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 HK$548
HK$1,160 total
includes taxes & fees
31 Mar - 1 Apr
Cozy studio in Andersonville Chicago
TV

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 HK$689
HK$1,578 total
includes taxes & fees
30 Mar - 31 Mar
1BR Apartment in Chicago
TV

Chic 2BR Haven Near Irving Park

Chic 2BR Haven Near Irving Park
Irving Park
9.8 out of 10, Exceptional, (10 reviews)
"Pictures were accurate, instructions were clear"
United States
Claire C.
The price is HK$807
HK$1,804 total
includes taxes & fees
6 Apr - 7 Apr
Chic 2BR Haven Near Irving Park
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 HK$1,057
HK$1,977 total
includes taxes & fees
3 Apr - 4 Apr
Just remodeled apartment close to airport and mall
TV

Cozy 2BR Apartment w/ Washer & Dryer

Cozy 2BR Apartment w/ Washer & Dryer
Portage Park
The price is HK$768
HK$1,797 total
includes taxes & fees
30 Mar - 31 Mar
Cozy 2BR Apartment w/ Washer & Dryer
Lobby

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 HK$564
HK$1,870 total
includes taxes & fees
30 Mar - 31 Mar
Bright Garden Studio
Outdoor dining

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 HK$1,245
HK$2,648 total
includes taxes & fees
30 Mar - 31 Mar
Tiny Home Retreat with hot tub
TV, offices

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.
The price is HK$689
HK$1,559 total
includes taxes & fees
30 Mar - 31 Mar
1BR/1BA City Comfort
2 bedrooms, iron/ironing board, travel cot, WiFi

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 HK$768
HK$1,797 total
includes taxes & fees
30 Mar - 31 Mar
2BR Cozy & Functional Unit
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, (78 reviews)
"Great stay. Even got to see deer on our last day. Thank you"
United States
Victoria D.
The price is HK$768
HK$1,520 total
includes taxes & fees
6 Apr - 7 Apr
Master qtr close to nature & easy urban facilities
Outdoor dining

Hot Tub Retreats

Hot Tub Retreats
Lake Villa
The price is HK$1,559
HK$2,225 total
includes taxes & fees
30 Mar - 31 Mar
Hot Tub Retreats
Fridge, microwave, oven, stovetop

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 HK$689
HK$1,523 total
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.
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Top Highwood Hotel Reviews

Hyatt Place Chicago/O'Hare Airport

Hyatt Place Chicago/O'Hare Airport

8/10 Good
"Room was comfy and very clean, breakfast good shuttle good and convenient and close to shops and restaurants easy to walk. All staff from shuttle drivers to hotel line and helpful. We will stay again very good price for the quality. Thanks. "
Amada 1-night trip
Posted 2 hours ago
Hyatt Place 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
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  • 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 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.