Highwood Holiday Rentals

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Our top choices for Highwood holiday rentals

10.0 out of 10, Exceptional, (49 reviews)
"It was perfect for a concert at the aragon ballroom, it was only a block away!"
United States
Maria G.
The price is AU$343
includes taxes & fees
1 Feb - 2 Feb
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
10.0 out of 10, Exceptional, (1 review)
"This was everything in the description and more! Pet friendly, clean, quiet, spacious, and well-stocked! Our only regret was not being able to enjoy the nice yard and firepit because of the frigid temperatures. Our host was responsive friendly, and helpful. Excellent experience all the way around!"
United States
David B.
The price is AU$323
includes taxes & fees
28 Jan - 29 Jan
Peaceful & Quiet. Close to Great Lakes, prime outlet, Winthrop Harbor Marina.
9.0 out of 10, Wonderful, (19 reviews)
"Everything was great! Definitely recommend "
United States
Monica T.
The price is AU$347
includes taxes & fees
2 Feb - 3 Feb
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

Apartment in Albany Park

Comfortable 2BR Chicago Apt
9.6 out of 10, Exceptional, (4 reviews)
"Perfect location for our trip. Very functional and comfortable. "
United States
Michael
The price is AU$280
includes taxes & fees
1 Feb - 2 Feb
Comfortable 2BR Chicago Apt
10.0 out of 10, Exceptional, (1 review)
"The property was beautiful and relaxing. Our host was wonderful and responded quickly to any questions we had. "
United States
Danielle S.
The price is AU$758
includes taxes & fees
3 Feb - 4 Feb
Newly remodeled Near Lake 4BR Hot Tub Navy Family home

Apartment in Albany Park

Warm & Stylish 2BR Apt
10.0 out of 10, Exceptional, (2 reviews)
"Clean and warm (on a bitter winter’s night)"
United States
Thomas V.
The price is AU$280
includes taxes & fees
2 Feb - 3 Feb
Warm & Stylish 2BR Apt

Apartment in Edgewater

Relaxing Chicago Studio
10.0 out of 10, Exceptional, (48 reviews)
"Had a great stay. Great location. "
United States
Justin
The price is AU$208
includes taxes & fees
28 Jan - 29 Jan
Relaxing Chicago Studio

Apartment in Lincoln Square

Cozy & Furnished 2BR Unit
9.2 out of 10, Wonderful, (16 reviews)
"Nice location "
United States
tom b.
The price is AU$258
includes taxes & fees
1 Feb - 2 Feb
Cozy & Furnished 2BR Unit
10.0 out of 10, Exceptional, (5 reviews)
"This spot was perfect for our Chicago visit where we mostly needed a place to sleep, not hang out. It seemed to have been refinished recently, so beds were comfy, bathroom lovely, and sitting area big enough for the two of us. "
United States
Deb B.
The price is AU$406
includes taxes & fees
28 Jan - 29 Jan
Private Chicago Apartment with Free Street Parking and In Unit Washer Dryer

Apartment in Irving Park

1BR Apt with a Warm, Welcoming Feel
9.0 out of 10, Wonderful, (4 reviews)
"It was wonderful and wil stay agian"
United States
Crystal P.
The price is AU$247
includes taxes & fees
1 Feb - 2 Feb
1BR Apt with a Warm, Welcoming Feel
8.4 out of 10, Very good, (7 reviews)
"The apartment was just as advertised and fit my needs. The A/C went down the first day and the host was extremely responsive and got it fixed right away. The location is perfect and and extremely convenient. 10/10 would stay again!"
United States
Rich K.
The price is AU$233
includes taxes & fees
28 Jan - 29 Jan
Stunning & Stylish Downtown Studio - Highland Park

Apartment in Portage Park

Homey 2BR Apt w/ Parking
9.4 out of 10, Exceptional, (9 reviews)
"It was clean and well maintained unit. It’s next to grocery store and pharmacy which was very convenient. It’s not too far from downtown. I would stay again here in future if available."
United States
Jatin
The price is AU$280
includes taxes & fees
1 Feb - 2 Feb
Homey 2BR Apt w/ Parking

Apartment in Portage Park

Trendy & Comfy Studio Unit
9.6 out of 10, Exceptional, (5 reviews)
"Older property. Landlord special in the bathroom. Definitely needs better window coverings. Otherwise, comfortable, safe, and clean. "
United States
Courtney V.
The price is AU$227
includes taxes & fees
1 Feb - 2 Feb
Trendy & Comfy Studio Unit
10.0 out of 10, Exceptional, (1 review)
"This is a wonderful space to enjoy time with family/friends. We hosted a birthday party and sleepover for young teens. The garage space was a perfect spot for a hangout. It was spacious for the sleepover and comfortable for everyone. It is close to modern conveniences. The host agency was super responsive!"
United States
Lisa Y.
The price is AU$756
includes taxes & fees
9 Feb - 10 Feb
Manor creek Vacation Getaway-Navy-PrivateYard-Game
9.2 out of 10, Wonderful, (7 reviews)
"clean and comfortable "
United States
Joseph S.
The price is AU$359
includes taxes & fees
28 Jan - 29 Jan
Cozy apartment with AC and WiFi in awesome Chicago

Apartment in Lincoln Square

Homey 1BR Space Apartment
9.8 out of 10, Exceptional, (13 reviews)
"Clean and great location"
United States
Margo M.
The price is AU$247
includes taxes & fees
1 Feb - 2 Feb
Homey 1BR Space Apartment

Apartment in Belmont Cragin

2BR Cozy & Functional Unit
10.0 out of 10, Exceptional, (1 review)
"The host was available and helpful at check-in. The 2 bedroom apartment was clean and well stocked. We felt safe and at home. We slept well. We did not notice any street noise at night. We had more than we epected and everything we needed.It might be helpful to color code the keys with nail polish or something. The three locks to get into the unit felt like a struggle because we needed a quick turn around time between events. Otherwise, it was a great stay!!"
United States
Laura V.
The price is AU$280
includes taxes & fees
1 Feb - 2 Feb
2BR Cozy & Functional Unit
9.4 out of 10, Exceptional, (6 reviews)
"Great neighborhood, easy check in/out. "
United States
Leah B.
The price is AU$222
includes taxes & fees
28 Jan - 29 Jan
Sunny Studio in Heart of Ravenswood
9.6 out of 10, Exceptional, (56 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is AU$438
includes taxes & fees
28 Jan - 29 Jan
2-bedroom apartment just 2 minutes drive to Wrigley Field
9.2 out of 10, Wonderful, (5 reviews)
"Cleanliness. Roomy. Comfortable mattresses. Fluffy, white bath towels. Ample towel racks in bathrooms. Attentive hostess. Off street parking greatly appreciated but garage door opener should be operative."
United States
MARGARET L.
The price is AU$290
includes taxes & fees
2 Feb - 3 Feb
Lovely 2BR with Parking Near United Center & Wrigley
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$190 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?

Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!: This holiday home rental outside of Highwood offers a furnished patio, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 10 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, 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 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.