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Holiday Rentals in Highwood

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Holiday Rentals in Highwood

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (70)
"Good people great breakfast "
The price is €219
includes taxes & fees
13 Jul - 14 Jul
The Gem Museum Suites

Huge Projector and Designated Workspace - Near Wrigley!

Huge Projector and Designated Workspace - Near Wrigley!

Luxurious 3 Bedroom Apartment in Chicago

9.6 out of 10, Exceptional, (12)
"Great property! Would visit again!"
Luxurious 3 Bedroom Apartment in Chicago

Cozy studio in Andersonville Chicago

9.2 out of 10, Wonderful, (10)
"I thought I was in a $300 night hotel, private, and serene surrounding"
The price is €154
includes taxes & fees
15 Jul - 16 Jul
Cozy studio in Andersonville Chicago

Nice 1BR Spot, Unwind & Relax

The price is €159
includes taxes & fees
13 Jul - 14 Jul
Nice 1BR Spot, Unwind & Relax

Charming 3-bedroom apartment with AC and WiFi in Waukegan.

9.0 out of 10, Wonderful, (6)
The price is €318
includes taxes & fees
11 Jul - 12 Jul
Charming 3-bedroom apartment with AC and WiFi in Waukegan.

2-bedroom apartment just 2 minutes drive to Wrigley Field

2.0 star property
9.4 out of 10, Exceptional, (28)
"Easy to find, slept like a baby. "
The price is €338
includes taxes & fees
27 Jul - 28 Jul
2-bedroom apartment just 2 minutes drive to Wrigley Field

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

The price is €920
includes taxes & fees
15 Jul - 16 Jul
Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater

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

5.2 out of 10, (5)
"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 €183
includes taxes & fees
5 Aug - 6 Aug
"Cozy Rooms with WiFi, Fitness Room & On-Site Restaurant/Bar in Schaumburg "

4BR Retreat w/ Theater, Game Room & Backyard

10.0 out of 10, Exceptional, (2)
"Comfy beds and a great house for kids and adults."
The price is €544
includes taxes & fees
22 Jul - 23 Jul
4BR Retreat w/ Theater, Game Room & Backyard

Great 3 bedroom rental unit near Logan Square

9.4 out of 10, Exceptional, (43)
"Safe neighborhood and super responsive host. I would definitely book again."
Great 3 bedroom rental unit near Logan Square

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

10.0 out of 10, Exceptional, (34)
"This was convenient and check-in process was easy. We would stay here again."
The price is €214
includes taxes & fees
13 Jul - 14 Jul
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Master qtr close to nature & easy urban facilities

9.8 out of 10, Exceptional, (56)
"Great trip "
The price is €175
includes taxes & fees
14 Jul - 15 Jul
Master qtr close to nature & easy urban facilities

Charming Wrigleyville Home Close to the Cubs!

9.4 out of 10, Exceptional, (25)
"Great neighborhood. Free and easy parking. "
Charming Wrigleyville Home Close to the Cubs!

Relaxing Chicago Studio

10.0 out of 10, Exceptional, (1)
"The location was perfect. It was clean and just as pictured. For a studio, it had plenty of room. "
The price is €181
includes taxes & fees
14 Jul - 15 Jul
Relaxing Chicago Studio

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

Spacious 3BR | 2BA Family-Friendly Home

Spacious 3BR | 2BA Family-Friendly Home

SPACIOUS 3BD - 2BA DUPLEX WITH FAMILY ROOM, KING BED-LAUNDRY ROOM & FIREPLACE

10.0 out of 10, Exceptional, (84)
"Easy to get to and very clean. Also check in and out was easy as well. "
SPACIOUS 3BD - 2BA DUPLEX WITH FAMILY ROOM, KING BED-LAUNDRY ROOM & FIREPLACE

Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!

4.0 star property
9.4 out of 10, Exceptional, (40)
"The large number of bedrooms provides privacy for a lot of people."
Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!

Quaint Bungalow, near Great Lakes Naval Base

10.0 out of 10, Exceptional, (61)
"Great experience, lots of cooking materials "
The price is €268
includes taxes & fees
13 Jul - 14 Jul
Quaint Bungalow, near Great Lakes Naval Base
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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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 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.