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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 AU$355
includes taxes & fees
28 Oct - 29 Oct
The Gem Museum Suites

Relaxing Chicago Studio

10.0 out of 10, Exceptional, (16)
"Had a great stay. Great location. "
The price is AU$292
includes taxes & fees
22 Oct - 23 Oct
Relaxing Chicago Studio

Cozy studio in Andersonville Chicago

9.2 out of 10, Wonderful, (34)
"Great studio apartment. Needed just one night and worth the price. Would recommend."
The price is AU$255
includes taxes & fees
27 Oct - 28 Oct
Cozy studio in Andersonville Chicago

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 AU$276
includes taxes & fees
5 Oct - 6 Oct
Nice 1BR Spot, Unwind & Relax

Luxurious 3 Bedroom Apartment in Chicago

9.4 out of 10, Exceptional, (30)
"The place was nice, clean, and in a beautiful neighborhood. "
Luxurious 3 Bedroom Apartment in Chicago

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 AU$515
includes taxes & fees
15 Oct - 16 Oct
2-bedroom apartment just 2 minutes drive to Wrigley Field

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 AU$465
includes taxes & fees
6 Oct - 7 Oct
2BR Fitness Pad • Private Gym • Sleeps 7

Charming Wrigleyville Home Close to the Cubs!

9.4 out of 10, Exceptional, (36)
"Great stay"
Charming Wrigleyville Home Close to the Cubs!

Master qtr close to nature & easy urban facilities

9.8 out of 10, Exceptional, (67)
"Beautiful, quiet space."
The price is AU$299
includes taxes & fees
3 Nov - 4 Nov
Master qtr close to nature & easy urban facilities

Sleeps 4 • Stylish Stay with Workspace

9.8 out of 10, Exceptional, (7)
The price is AU$580
includes taxes & fees
10 Oct - 11 Oct
Sleeps 4 • Stylish Stay with Workspace

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

10.0 out of 10, Exceptional, (108)
"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!

Prime City Stay in a 1BR Apt

9.2 out of 10, Wonderful, (10)
"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 AU$276
includes taxes & fees
6 Oct - 7 Oct
Prime City Stay in a 1BR Apt

Montrose Studio:Your Uptown Base

9.6 out of 10, Exceptional, (4)
"The property was exactly as pictured. The area was safe, had restaurants and coffee shops within a short walk. "
The price is AU$270
includes taxes & fees
2 Nov - 3 Nov
Montrose Studio:Your Uptown Base

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 AU$543
includes taxes & fees
14 Oct - 15 Oct
2BR • Newly Furnished Modern Apt • Near O`Hare

Uptown Studio Gem Sum

7.2 out of 10, Good, (5)
The price is AU$270
includes taxes & fees
3 Nov - 4 Nov
Uptown Studio Gem Sum

Chic apartment with fitness room and AC in beautiful Chicago

6.8 out of 10, (3)
"Didn’t receive check in information until after book in time. This was after repeated messages, calls to property manager & VRBO. The actual apartment was tidy, however the drain in the tub was clogged. Parking was difficult and when asked if we could park in the lot behind the apartment, we were told it was 20 more a day. Was allowed to park there the second night at no cost. Communication once we were actually checked in was good. It’s in a lovely neighborhood and close to the train and...
The price is AU$392
includes taxes & fees
21 Oct - 22 Oct
Chic apartment with fitness room and AC in beautiful Chicago

Sleeps 18 • 8BR • Game Room • Gym • Theater

5.4 out of 10, (3)
"Great space for large groups. Park across the street is a great "feature"."
The price is AU$1,486
includes taxes & fees
27 Oct - 28 Oct
Sleeps 18 • 8BR • Game Room • Gym • Theater

Cozy 1BR in Walkable Area

9.6 out of 10, Exceptional, (5)
"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...
The price is AU$280
includes taxes & fees
6 Oct - 7 Oct
Cozy 1BR in Walkable Area

Sunny Studio in Heart of Ravenswood

9.0 out of 10, Wonderful, (4)
"Great neighborhood, easy check in/out. "
The price is AU$276
includes taxes & fees
28 Oct - 29 Oct
Sunny Studio in Heart of Ravenswood

Your Next Vacation Home

9.6 out of 10, Exceptional, (54)
"We enjoyed our stay"
The price is AU$527
includes taxes & fees
20 Oct - 21 Oct
Your Next Vacation Home
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 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$255 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?

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.