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Highwood Holiday Rentals

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Check prices for these dates

Tonight
28 Jul - 29 Jul
Tomorrow
29 Jul - 30 Jul
This weekend
1 Aug - 3 Aug
Next weekend
8 Aug - 10 Aug

Holiday Rentals in Highwood

The Gem Museum Suites
Kitchen area with dining space, featuring a refrigerator, round table, and two chairs.

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (80)
"Had a good and comfortable stay "
The price is HK$1,599
HK$1,831 total
includes taxes & fees
5 Aug - 6 Aug
The Gem Museum Suites
Huge Projector and Designated Workspace - Near Wrigley!
Restful retreat with a neatly made bed and a bedside lamp.

Huge Projector and Designated Workspace - Near Wrigley!

The price is HK$459
HK$2,187 total
includes taxes & fees
12 Aug - 13 Aug
Huge Projector and Designated Workspace - Near Wrigley!
Luxurious 3 Bedroom Apartment in Chicago
Enjoy cooking in this well-lit kitchen with a stainless steel sink and microwave.

Luxurious 3 Bedroom Apartment in Chicago

9.6 out of 10, Exceptional, (14)
"Great property! Would visit again!"
Luxurious 3 Bedroom Apartment in Chicago
Cozy studio in Andersonville Chicago
Relax in this inviting bedroom with a comfortable bed, sofa, and lush greenery.

Cozy studio in Andersonville Chicago

9.2 out of 10, Wonderful, (14)
"It was a great location, internet was a little spotty on streaming services but we were in walking distance to so much it was worth it "
The price is HK$706
HK$1,337 total
includes taxes & fees
11 Aug - 12 Aug
Cozy studio in Andersonville Chicago
Nice 1BR Spot, Unwind & Relax
TV

Nice 1BR Spot, Unwind & Relax

10.0 out of 10, Exceptional, (5)
The price is HK$691
HK$1,415 total
includes taxes & fees
30 Jul - 31 Jul
Nice 1BR Spot, Unwind & Relax
Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater
8 bedrooms, desk, iron/ironing board, travel cot

Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater

The price is HK$2,146
HK$8,344 total
includes taxes & fees
18 Aug - 19 Aug
Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater
2-bedroom apartment just 2 minutes drive to Wrigley Field
Stroll through the beautifully maintained garden surrounding this charming two-story building with a covered porch area.

2-bedroom apartment just 2 minutes drive to Wrigley Field

2.0 star property
9.4 out of 10, Exceptional, (32)
"Easy to find, slept like a baby. "
The price is HK$1,053
HK$2,512 total
includes taxes & fees
29 Jul - 30 Jul
2-bedroom apartment just 2 minutes drive to Wrigley Field
3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi
Enjoy cooking and dining in this well-equipped kitchen with a gas stove, sink, and dining table.

3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi

9.0 out of 10, Wonderful, (7)
"We stayed here for my son’s Navy boot camp graduation, and overall it was a great experience. The home was clean and had everything we needed. The area was okay and felt safe. Communication with the owner was smooth—she responded quickly and was very helpful. The location was super convenient, only about 10 minutes from the base. I would definitely recommend this place for anyone attending a graduation or visiting the area."
The price is HK$1,452
HK$2,842 total
includes taxes & fees
29 Jul - 30 Jul
3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi
"Cozy Rooms with WiFi, Fitness Room & On-Site Restaurant/Bar in Schaumburg "
Enjoy a drink at the hotel's bar, where a long counter and comfortable stools await.

"Cozy Rooms with WiFi, Fitness Room & On-Site Restaurant/Bar in Schaumburg "

5.0 out of 10, (6)
"Room clean, fitness room awful!! Have to request house keeping but they do not change sheets. Bar and restaurant bare minimum. They have a nice bar next to hotel(Not the-one located in the hotel) Would not stay again!"
The price is HK$1,311
HK$1,483 total
includes taxes & fees
29 Jul - 30 Jul
"Cozy Rooms with WiFi, Fitness Room & On-Site Restaurant/Bar in Schaumburg "
Great 3 bedroom rental unit near Logan Square
Enjoy cooking in this well-equipped kitchen with a coffee maker and ample countertop space.

Great 3 bedroom rental unit near Logan Square

9.6 out of 10, Exceptional, (49)
"This is a really cute property close to a lot of neighborhood restaurants and bars. The host is really nice and even moved his car for us so we could have his spot when we arrived. We would definitely stay here again. "
Great 3 bedroom rental unit near Logan Square
4BR Retreat w/ Theater, Game Room & Backyard
Enjoy meals in this dining area with a wooden table, white chairs, and a large mirror.

4BR Retreat w/ Theater, Game Room & Backyard

10.0 out of 10, Exceptional, (4)
"Great place"
The price is HK$1,245
HK$4,948 total
includes taxes & fees
20 Aug - 21 Aug
4BR Retreat w/ Theater, Game Room & Backyard
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Relax in a spacious room with high ceilings and large windows, featuring a comfortable seating area and a crib for a family-friendly stay.

Riverfront Libertyville Retreat w/ Outdoor Kitchen

8.6 out of 10, Excellent, (28)
"Amazing property!! Great location communication with owners throughout our stay. This made our stay with our sailor perfect."
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Enjoy breathtaking views of the city from this rooftop terrace with a glass door and windows.

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

10.0 out of 10, Exceptional, (37)
"This was convenient and check-in process was easy. We would stay here again."
The price is HK$455
HK$1,758 total
includes taxes & fees
11 Aug - 12 Aug
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Relax in this spacious living room with a large L-shaped sofa, smaller sofa, and chaise lounge.

Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families

9.0 out of 10, Wonderful, (31)
"Had fun"
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Tiny Home Retreat with hot tub
Outdoor dining

Tiny Home Retreat with hot tub

The price is HK$911
HK$2,144 total
includes taxes & fees
29 Jul - 30 Jul
Tiny Home Retreat with hot tub
Master qtr close to nature & easy urban facilities
Stunning home with a covered porch, large windows, and beautifully landscaped yard.

Master qtr close to nature & easy urban facilities

9.8 out of 10, Exceptional, (58)
"Great spot."
The price is HK$841
HK$1,508 total
includes taxes & fees
29 Jul - 30 Jul
Master qtr close to nature & easy urban facilities
Your Chicago Home Base – 4BR, 2BA, Sleeps 13, Ideal for Families & Groups!
Stunning residential area with a brick building, satellite dish, and lush greenery.

Your Chicago Home Base – 4BR, 2BA, Sleeps 13, Ideal for Families & Groups!

10.0 out of 10, Exceptional, (5)
Your Chicago Home Base – 4BR, 2BA, Sleeps 13, Ideal for Families & Groups!
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Enjoy breathtaking views of the city from this rooftop terrace with a metal railing and paved floor.

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

8.6 out of 10, Excellent, (15)
"Loved the space, nice decor, clean. Perfect for 2 people."
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Relaxing Chicago Studio
Two single beds with white linens and grey headboards, set against a light-colored backdrop.

Relaxing Chicago Studio

10.0 out of 10, Exceptional, (3)
"Had a great stay. Great location. "
The price is HK$706
HK$1,483 total
includes taxes & fees
11 Aug - 12 Aug
Relaxing Chicago Studio
Elegant 3 Bedroom and 1 Bath Apartment
Cozy retreat with a large bed, patterned bedspread, and diamond-shaped wall decorations.

Elegant 3 Bedroom and 1 Bath Apartment

9.0 out of 10, Wonderful, (10)
"Very nice place - can easily fit quite a few people! Host was very accommodating, place was clean and comfortable. My friends and I had a great time! "
Elegant 3 Bedroom and 1 Bath Apartment
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

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

10/10 Excellent
"Everything "
Ciara 2-night trip
Posted 9 hours ago
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

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?

Great 3 bedroom rental unit near Logan Square: This holiday home rental outside of Highwood is located on a lake, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that 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 Chicago Botanic Garden. 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.