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Highwood Holiday Rentals

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Holiday Rentals in Highwood

Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake
9.8 out of 10, Exceptional, (11)
"Very, very clean. Peaceful. I slept well. "
The price is AU$332
includes taxes & fees
22 Oct - 23 Oct
Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake
Nice 1BR Spot, Unwind & Relax
10.0 out of 10, Exceptional, (17)
"Great stay"
The price is AU$280
includes taxes & fees
19 Oct - 20 Oct
Nice 1BR Spot, Unwind & Relax
Relaxing Chicago Studio
10.0 out of 10, Exceptional, (23)
"Had a great stay. Great location. "
The price is AU$268
includes taxes & fees
4 Nov - 5 Nov
Relaxing Chicago Studio
Montrose Studio:Your Uptown Base
9.6 out of 10, Exceptional, (5)
"The property was exactly as pictured. The area was safe, had restaurants and coffee shops within a short walk. "
The price is AU$273
includes taxes & fees
3 Nov - 4 Nov
Montrose Studio:Your Uptown Base
1BR Apartment in Chicago
9.4 out of 10, Exceptional, (6)
"Good location for us. Host was easy to communicate with"
The price is AU$278
includes taxes & fees
4 Nov - 5 Nov
1BR Apartment in Chicago
Spacious 2BR Near Dining & Shops
8.0 out of 10, Very good, (6)
"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 AU$327
includes taxes & fees
3 Nov - 4 Nov
Spacious 2BR Near Dining & Shops
Stylish 1BR Stay in Irving Vibes
10.0 out of 10, Exceptional, (1)
"The apartment was in a nice area. It was clean and included appropriate amenities. Bed was comfortable. Thanks!"
The price is AU$278
includes taxes & fees
12 Nov - 13 Nov
Stylish 1BR Stay in Irving Vibes
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
8.8 out of 10, Excellent, (17)
"Good communication from owner regarding check in and options for nearby parking. I would stay here again."
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
2BR Getaway - Comfy & Ready
10.0 out of 10, Exceptional, (4)
"Great location "
The price is AU$327
includes taxes & fees
4 Nov - 5 Nov
2BR Getaway - Comfy & Ready
Elegant 2BR Apartment w/ In-Unit Laundry
9.6 out of 10, Exceptional, (4)
"The was a great place to stay! Would totally recommend and stay again!! "
The price is AU$315
includes taxes & fees
10 Nov - 11 Nov
Elegant 2BR Apartment w/ In-Unit Laundry
Great Layout – Spacious 2BR Apt
10.0 out of 10, Exceptional, (4)
"Clean, comfortable, and would definitely stay again!"
The price is AU$321
includes taxes & fees
11 Nov - 12 Nov
Great Layout – Spacious 2BR Apt
Chic & Fully Furnished 2BR Apt!
10.0 out of 10, Exceptional, (2)
"Our stay was great! The apartment is very clean and comfortable. Nicely furnished. On a residential street in a lovely neighborhood. Wifi and A/C units worked well (we were there in August). We found street parking pretty easily. And Kristine was a really responsive host. Would absolutely stay again!"
The price is AU$327
includes taxes & fees
4 Nov - 5 Nov
Chic & Fully Furnished 2BR Apt!
Special Skevanston Space 2mi to Northwestern University & beach
9.0 out of 10, Wonderful, (21)
"Me, my friends, and girlfriend all stayed here together for the weekend. We attended collect-a-con over in Rosemont and then also did a little day trip to downtown Chicago for mine and my friends birthday! It was really nice staying here, super cozy and cute. Very nice neighborhood and neighbors were friendly :)"
The price is AU$349
includes taxes & fees
21 Oct - 22 Oct
Special Skevanston Space 2mi to Northwestern University & beach
Cozy 3BR Gem in North Center
9.0 out of 10, Wonderful, (6)
The price is AU$337
includes taxes & fees
19 Oct - 20 Oct
Cozy 3BR Gem in North Center
Chic Studio in Heart of Chicago
9.4 out of 10, Exceptional, (3)
"Older property. Landlord special in the bathroom. Definitely needs better window coverings. Otherwise, comfortable, safe, and clean. "
The price is AU$294
includes taxes & fees
5 Nov - 6 Nov
Chic Studio in Heart of Chicago
Comfortable 2BR Chicago Apt
9.6 out of 10, Exceptional, (4)
"Perfect location for our trip. Very functional and comfortable. "
The price is AU$330
includes taxes & fees
28 Oct - 29 Oct
Comfortable 2BR Chicago Apt
Sunny Studio in Heart of Ravenswood
9.0 out of 10, Wonderful, (4)
"Great neighborhood, easy check in/out. "
The price is AU$263
includes taxes & fees
10 Nov - 11 Nov
Sunny Studio in Heart of Ravenswood
1BR Chic & Sunny Place
9.4 out of 10, Exceptional, (3)
"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 AU$334
includes taxes & fees
12 Nov - 13 Nov
1BR Chic & Sunny Place
Cozy & Furnished 2BR Unit
9.4 out of 10, Exceptional, (10)
"This lovely 2 bedroom apartment was just perfect for our visit. It's just a few blocks to fun Lincoln Park which has lots of little shops & great restaurants. Best of all it was just a short walk to our daughter's place. The apartment was very clean and the beds were super comfortable. Any questions we had were answered quickly. Big screen TV in living room, well stocked kitchen and plenty of hot water for showers. Pretty sure we'll be back!"
The price is AU$330
includes taxes & fees
19 Oct - 20 Oct
Cozy & Furnished 2BR Unit
Uptown Studio Gem Sum
7.2 out of 10, Good, (5)
The price is AU$273
includes taxes & fees
3 Nov - 4 Nov
Uptown Studio Gem Sum
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

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 favourite 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 depend 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 AU$240 per night. Entering your travel dates in the search wizard might find you 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?

Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families : This holiday home rental outside of Highwood offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Make the most of games in this rental home to help you unwind.

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.