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Highwood Holiday Rentals

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Holiday Rentals in Highwood

Elegant 2BR Apartment w/ In-Unit Laundry

The price is NZ$361
includes taxes & fees
12 Aug - 13 Aug
Elegant 2BR Apartment w/ In-Unit Laundry

Spacious 4BR Retreat - Chase E1

2.0 out of 10, (1)
"3 hours before we were supposed to check-in they canceled. They had my cell phone and didn't contact me. I had messaged them to get check in information and was only told at that time the place was now unavailable. For something as important as cancelling last minute they should have called, messaged and emailed. They had no problem requiring me via my cell phone to give them not only give them the names and ages of every guest staying but a picture of my passport and CC. Was this just a scam to...
The price is NZ$711
includes taxes & fees
28 July - 29 July
Spacious 4BR Retreat - Chase E1

Great Layout – Spacious 2BR Apt

The price is NZ$330
includes taxes & fees
15 July - 16 July
Great Layout – Spacious 2BR Apt

Chic apartment with fitness room and AC in beautiful Chicago

The price is NZ$507
includes taxes & fees
13 July - 14 July
Chic apartment with fitness room and AC in beautiful 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 NZ$263
includes taxes & fees
14 July - 15 July
Cozy studio in Andersonville Chicago

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 NZ$282
includes taxes & fees
14 July - 15 July
Relaxing Chicago Studio

Peaceful 1BR Escape in Evanston

10.0 out of 10, Exceptional, (2)
"Great for a quick trip to Chicago. Walkable to lakefront beach, restaurants, grocery stores, coffee chops. Less than a block to the train for downtown Chicago. Beautiful apartment, very spacious. Kitchen has everything you need to cook meals, make coffee, etc. Relaxing atmosphere, charming neighborhood. "
The price is NZ$323
includes taxes & fees
28 July - 29 July
Peaceful 1BR Escape in Evanston

1BR Chic & Sunny Place

10.0 out of 10, Exceptional, (1)
"Location was perfect for visiting family and getting around the city. Bed was extra comfy and the AC worked wonderfully. Will stay here again on our next visit. "
The price is NZ$304
includes taxes & fees
13 July - 14 July
1BR Chic & Sunny Place

Cozy & Furnished 2BR Unit

The price is NZ$330
includes taxes & fees
13 July - 14 July
Cozy & Furnished 2BR Unit

Lovely 1BR in Evanston w/Laundry

The price is NZ$346
includes taxes & fees
22 July - 23 July
Lovely 1BR in Evanston w/Laundry

Light-Filled 1-Bedroom Apt

10.0 out of 10, Exceptional, (1)
The price is NZ$304
includes taxes & fees
15 July - 16 July
Light-Filled 1-Bedroom Apt

PROMO 10% WEEKLY AND 15% MONTHLY Near Northwestern, Beaches Parking Fenced Yard

9.6 out of 10, Exceptional, (9)
"Excellent with every detail our host was awesome ! Location great,! And Clean house Comfy Experience!"
PROMO 10% WEEKLY AND 15% MONTHLY Near Northwestern, Beaches Parking Fenced Yard

1BR Spot, Fully Furnished

The price is NZ$360
includes taxes & fees
23 July - 24 July
1BR Spot, Fully Furnished

Cozy Private & Spacious 6-bedroom Duplex with Parking in charming Evanston

2.0 star property
10.0 out of 10, Exceptional, (2)
"Good place to hang out with friends."
The price is NZ$1,698
includes taxes & fees
30 July - 31 July
Cozy Private & Spacious 6-bedroom Duplex with Parking in charming Evanston

Comfortable 2BR Chicago Apt

The price is NZ$325
includes taxes & fees
23 July - 24 July
Comfortable 2BR Chicago Apt

Roscoe Retreat · Cozy 2BR in Chicago

The price is NZ$327
includes taxes & fees
15 July - 16 July
Roscoe Retreat · Cozy 2BR in Chicago

Prime City Stay in a 1BR Apt

9.0 out of 10, Wonderful, (2)
"Location is very good, 10 mins walk to irving blue line station, and the apartment has lot of light during the day as it was a corner unit."
The price is NZ$300
includes taxes & fees
15 July - 16 July
Prime City Stay in a 1BR Apt

Culinary DREAM - Tranquil Home - Pizza Oven/BBQ/Smoker

9.4 out of 10, Exceptional, (3)
"The home was very clean, well appointed and comfortable. 6 adults stayed comfortably in the home. "
The price is NZ$1,324
includes taxes & fees
15 July - 16 July
Culinary DREAM - Tranquil Home - Pizza Oven/BBQ/Smoker

Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS

10.0 out of 10, Exceptional, (31)
"So green and cozy "
The price is NZ$1,317
includes taxes & fees
11 Aug - 12 Aug
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS

1BR Vibrant & Inviting Apt in Chicago

The price is NZ$300
includes taxes & fees
15 July - 16 July
1BR Vibrant & Inviting Apt in Chicago
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.