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Highwood Holiday Rentals

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Holiday Rentals in Highwood

Apartment in Uptown

10.0 out of 10, Exceptional, (48)
"Clean room and the host was great with communication "
United States
Heather T.
The price is AU$363
includes taxes & fees
8 Dec - 9 Dec
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Apartment in Ravenswood

9.8 out of 10, Exceptional, (12)
"Great location. Very walkable to restaurants and bars. Awesome park nearby. Host was easy to communicate with. "
United States
Kayla K.
The price is AU$257
includes taxes & fees
4 Jan - 5 Jan 2026
Homey 1BR Space Apartment

Apartment in Avondale

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!"
United States
Stephanie D.
The price is AU$299
includes taxes & fees
8 Dec - 9 Dec
Chic & Fully Furnished 2BR Apt!

Apartment in South Evanston

10.0 out of 10, Exceptional, (1)
"The apartment was very clean and the bed was super comfortable. We slept great. We didn’t spend much time at the apartment but for our trip it was exactly what we needed. "
United States
V S.
The price is AU$252
includes taxes & fees
4 Jan - 5 Jan 2026
Perfectly Located 1-Bedroom Unit

Apartment in Rogers Park

10.0 out of 10, Exceptional, (5)
"Clean, comfortable, and would definitely stay again!"
United States
KM W.
The price is AU$274
includes taxes & fees
8 Dec - 9 Dec
Great Layout – Spacious 2BR Apt

Apartment in South Evanston

10.0 out of 10, Exceptional, (4)
"Area was quiet and homey. We stayed in both nights we stayed, however there were plenty of things to eat nearby. The coffee shop around the corner was nice. We had a fabulous time. We would stay at this property again."
United States
Robert D.
The price is AU$252
includes taxes & fees
4 Jan - 5 Jan 2026
Charming 1BR Apt in Evanston

Apartment in Ravenswood

9.8 out of 10, Exceptional, (7)
"We loved staying here! Would 100% stay again.Really clean and comfortable! Loved the mattress. Easy check in and out. Close to great businesses for dining or shopping. Close to the Brown line and a few buses for all our transit needs. Air-conditioned, thank god! There were all the amenities you expect like pots and pans, soap and shampoo in the shower, and even an iron and ironing board! We felt a lot like locals for our short 5 day stay!Basically perfect except for some small issues. The...
United States
Ariel k.
The price is AU$257
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy 1BR in Walkable Area

Apartment in South Evanston

8.4 out of 10, Very good, (6)
"Quiet, clean and spacious! A peaceful neighborhood. "
United States
Efemena A.
The price is AU$252
includes taxes & fees
1 Jan - 2 Jan 2026
Peaceful 1BR Escape in Evanston

Apartment in Edgewater

9.0 out of 10, Wonderful, (10)
"It was a awesome location and clean and spacious for what we needed."
United States
porschea t.
The price is AU$271
includes taxes & fees
11 Dec - 12 Dec
Stylish and Roomy 2BR in Chicago

Apartment in Ravenswood

9.8 out of 10, Exceptional, (24)
"Great stay"
United States
Kayla K.
The price is AU$257
includes taxes & fees
1 Jan - 2 Jan 2026
Nice 1BR Spot, Unwind & Relax

Apartment in Uptown

9.4 out of 10, Exceptional, (6)
"It was a great stay if you want to experience a diverse, fun, authentic Chicago neigborhood. We really enjoyed it. "
United States
Amer
The price is AU$226
includes taxes & fees
10 Dec - 11 Dec
Sunny Studio in Heart of Ravenswood

Apartment in Irving Park

9.8 out of 10, Exceptional, (8)
"Beautiful place. The host was awesome with communication and recommendations. Will definitely stay again when we come to the city"
United States
Katie L.
The price is AU$299
includes taxes & fees
8 Dec - 9 Dec
Chic 2BR Haven Near Irving Park

Apartment in Uptown

8.8 out of 10, Excellent, (18)
"Had a great stay! Perfect for our needs. Great location. It was an easy walk to the lake and lots of great restaurants nearby!"
United States
Rodney S.
The price is AU$363
includes taxes & fees
11 Dec - 12 Dec
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

Apartment in Ravenswood

10.0 out of 10, Exceptional, (2)
"Clean quiet apartment just a block away from the train! Very convenient and there's a Starbucks right down the street."
United States
Kevin D.
The price is AU$257
includes taxes & fees
4 Jan - 5 Jan 2026
1BR Pad with Homey Feel

Apartment in Rogers Park

9.6 out of 10, Exceptional, (8)
"Great location "
United States
Bernard M.
The price is AU$274
includes taxes & fees
14 Dec - 15 Dec
2BR Getaway - Comfy & Ready

Apartment in Irving Park

8.8 out of 10, Excellent, (3)
"It was wonderful and wil stay agian"
United States
Crystal P.
The price is AU$259
includes taxes & fees
10 Dec - 11 Dec
1BR Homey Apt in Irving Park

Apartment in Albany Park

10.0 out of 10, Exceptional, (1)
The price is AU$304
includes taxes & fees
7 Jan - 8 Jan 2026
Cozy & Inviting 2BR Apartment

Apartment in Rogers Park

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. "
United States
Ever
The price is AU$276
includes taxes & fees
8 Dec - 9 Dec
Spacious 2BR Near Dining & Shops

Apartment in Evanston

9.0 out of 10, Wonderful, (21)
"Very nice stay. Host was super nice and accommodating. "
United States
Melissa K.
The price is AU$329
includes taxes & fees
9 Dec - 10 Dec
Special Skevanston Space 2mi to Northwestern University & beach

Apartment in Albany Park

10.0 out of 10, Exceptional, (1)
"Met my expectations. Nice comfortable unit located in a great part of Chicago. Host was very responsive."
United States
Maureen B.
The price is AU$299
includes taxes & fees
8 Dec - 9 Dec
Warm & Stylish 2BR Apt
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$198 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, there are holiday rentals close to the most popular sights in Highwood, or you can select a more secluded option if you're looking for a relaxing stay. Highwood is known for its shopping and restaurants.

What are some of the best holiday rentals that Highwood has to offer?

Home -2 bedroom, 4k projector: This holiday home rental outside of Highwood has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

What can I see and do in Highwood?

While exploring the area, visit family-friendly sights like Northbrook Sports Complex, 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.