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Highwood Holiday Rentals

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Holiday Rentals in Highwood

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (89)
"Super nice hotel and staff "
The price is NZ$414
includes taxes & fees
5 Oct - 6 Oct
The Gem Museum Suites

Relaxing Chicago Studio

10.0 out of 10, Exceptional, (12)
"Had a great stay. Great location. "
The price is NZ$276
includes taxes & fees
29 Sept - 30 Sept
Relaxing Chicago Studio

Nice 1BR Spot, Unwind & Relax

10.0 out of 10, Exceptional, (16)
"This location was perfect for our nights in Chicago. We were within walking distance of great shopping and eating. "
The price is NZ$310
includes taxes & fees
1 Oct - 2 Oct
Nice 1BR Spot, Unwind & Relax

Cozy studio in Andersonville Chicago

9.2 out of 10, Wonderful, (33)
"Great studio apartment. Needed just one night and worth the price. Would recommend."
The price is NZ$276
includes taxes & fees
7 Oct - 8 Oct
Cozy studio in Andersonville Chicago

Luxurious 3 Bedroom Apartment in Chicago

9.4 out of 10, Exceptional, (27)
"The place was nice, clean, and in a beautiful neighborhood. "
Luxurious 3 Bedroom Apartment in Chicago

Sleeps 4 • Stylish Stay with Workspace

9.8 out of 10, Exceptional, (7)
The price is NZ$662
includes taxes & fees
10 Oct - 11 Oct
Sleeps 4 • Stylish Stay with Workspace

Uptown Studio Gem Sum

7.2 out of 10, Good, (5)
The price is NZ$305
includes taxes & fees
1 Oct - 2 Oct
Uptown Studio Gem Sum

2BR Fitness Pad • Private Gym • Sleeps 7

9.6 out of 10, Exceptional, (5)
"I really liked how quiet and nice it was around the area "
The price is NZ$507
includes taxes & fees
6 Oct - 7 Oct
2BR Fitness Pad • Private Gym • Sleeps 7

2-bedroom apartment just 2 minutes drive to Wrigley Field

2.0 star property
9.6 out of 10, Exceptional, (43)
"Great place to stay when you’re in town for the Cubbies! "
The price is NZ$617
includes taxes & fees
15 Oct - 16 Oct
2-bedroom apartment just 2 minutes drive to Wrigley Field

Prime City Stay in a 1BR Apt

9.2 out of 10, Wonderful, (9)
"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$310
includes taxes & fees
1 Oct - 2 Oct
Prime City Stay in a 1BR Apt

Master qtr close to nature & easy urban facilities

9.8 out of 10, Exceptional, (66)
"Beautiful, quiet space."
The price is NZ$367
includes taxes & fees
30 Sept - 1 Oct
Master qtr close to nature & easy urban facilities

Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!

10.0 out of 10, Exceptional, (107)
"Loved staying at Jamie’s place. Wonderful neighborhood and well kept apartment. Jamie was friendly and very helpful. "
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!

Charming Wrigleyville Home Close to the Cubs!

9.4 out of 10, Exceptional, (35)
"Great stay"
Charming Wrigleyville Home Close to the Cubs!

Stylish and Roomy 2BR in Chicago

8.6 out of 10, Excellent, (7)
The price is NZ$366
includes taxes & fees
29 Sept - 30 Sept
Stylish and Roomy 2BR in Chicago

Sleeps 7 • Huge Projector • Designated Workspace

6.0 out of 10, (4)
"Overall the property was fine. The remote for the garage door was missing and the dryer was not working properly. The dryer created the bigger issue needing to wash towels so everyone could shower daily. "
The price is NZ$497
includes taxes & fees
6 Oct - 7 Oct
Sleeps 7 • Huge Projector • Designated Workspace

Your Next Vacation Home

9.6 out of 10, Exceptional, (54)
"We enjoyed our stay"
The price is NZ$530
includes taxes & fees
29 Sept - 30 Sept
Your Next Vacation Home

North Chi retreat – Navy, Sauna, Tiki Bar, Games

9.8 out of 10, Exceptional, (8)
The price is NZ$825
includes taxes & fees
29 Sept - 30 Sept
North Chi retreat – Navy, Sauna, Tiki Bar, Games

2BR • Newly Furnished Modern Apt • Near O`Hare

7.6 out of 10, Good, (4)
"Great place! Nice, safe neighborhood. The host was very helpful. "
The price is NZ$612
includes taxes & fees
7 Oct - 8 Oct
2BR • Newly Furnished Modern Apt • Near O`Hare

Sunny Studio in Heart of Ravenswood

9.4 out of 10, Exceptional, (3)
"It was a great stay if you want to experience a diverse, fun, authentic Chicago neigborhood. We really enjoyed it. "
The price is NZ$327
includes taxes & fees
14 Oct - 15 Oct
Sunny Studio in Heart of Ravenswood

Spacious 2BR Near Dining & Shops

8.4 out of 10, Very good, (5)
"Loved this sweet space tucked into a special neighborhood in the city. Space was clean & comfortable, wonderful shower & a nice respite from city life. "
The price is NZ$366
includes taxes & fees
28 Sept - 29 Sept
Spacious 2BR Near Dining & Shops
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

Find out more about Highwood

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$276 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?

Master qtr close to nature & easy urban facilities: This holiday home rental outside of Highwood offers a garden, 1 hot tub and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and kitchenware.

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.