Holiday Rentals in Highwood

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Our top choices for Highwood holiday rentals

Bright Garden Studio

Bright Garden Studio
South Evanston
8.2 out of 10, Very good, (36 reviews)
"Easy access. Nice location. Available shrot notice."
United States
Drew H.
The price is €228
includes taxes & fees
10 Jun - 11 Jun
Bright Garden Studio

Cozy 2BR with King Beds + Full Kitchen

Cozy 2BR with King Beds + Full Kitchen
Portage Park
2.0 out of 10, (1 review)
The price is €216
includes taxes & fees
9 Jun - 10 Jun
Cozy 2BR with King Beds + Full Kitchen

Trendy & Comfy Studio Unit

Trendy & Comfy Studio Unit
Portage Park
9.2 out of 10, Wonderful, (7 reviews)
"It was really a great place. Bb oo"
United States
Kate S.
Trendy & Comfy Studio Unit

Mins from O'Hare • Safe Location • Private Parking

Mins from O'Hare • Safe Location • Private Parking
O'Hare
The price is €229
includes taxes & fees
9 Jun - 10 Jun
Mins from O'Hare • Safe Location • Private Parking

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
South Evanston
10.0 out of 10, Exceptional, (49 reviews)
"The place was awesome - very clean !! Great location !! "
United States
John R.
The price is €227
includes taxes & fees
9 Jun - 10 Jun
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More

Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (79 reviews)
"Great stay i loved it"
United States
Cedes W.
The price is €177
includes taxes & fees
23 Jun - 24 Jun
Cozy studio in Andersonville Chicago

Spacious 2BR Close to it All - Chic Apt in Skokie

Spacious 2BR Close to it All - Chic Apt in Skokie
West Dempster
9.0 out of 10, Wonderful, (2 reviews)
"Excellent communication with the host. Easy and secure access to the unit. Well furnished and perfect for my trip. So clean! "
United States
Jean W.
Spacious 2BR Close to it All - Chic Apt in Skokie

Sunlit Studio with City Charm

Sunlit Studio with City Charm
Rogers Park
8.4 out of 10, Very good, (13 reviews)
"Host was extremely welcoming and accommodating. They went out of their way to assure me that they were but a call away if there was anything we needed."
United States
Renee W.
Sunlit Studio with City Charm

F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC

F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
Barrington
9.8 out of 10, Exceptional, (9 reviews)
"Very nice little spot... Host was absolutely wonderful!!! Definitely stay here again!"
United States
Adam B.
The price is €154
includes taxes & fees
8 Jun - 9 Jun
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC

Sunny Work From Home Apt: Near Northwestern-Chicago-Beaches-Loyola

Sunny Work From Home Apt: Near Northwestern-Chicago-Beaches-Loyola
South Evanston
10.0 out of 10, Exceptional, (9 reviews)
"Everything was as described. I would stay here again."
United States
Brent S.
Sunny Work From Home Apt: Near Northwestern-Chicago-Beaches-Loyola

Spacious 2 Queen Beds,Nsmk|Kitchen|Studio 6 Vernon Hills

Spacious 2 Queen Beds,Nsmk|Kitchen|Studio 6 Vernon Hills
Chicago
10.0 out of 10, Exceptional, (18 reviews)
"Good place to stay,,"
United States
Anonymous traveller
The price is €95
includes taxes & fees
2 Jul - 3 Jul
Spacious 2 Queen Beds,Nsmk|Kitchen|Studio 6 Vernon Hills

Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base
Mundelein
9.8 out of 10, Exceptional, (72 reviews)
"We had a great stay! The area was peaceful and felt safe. "
United States
Yoselin V.
Quaint Bungalow, near Great Lakes Naval Base

Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (83 reviews)
"nice little place! quiet area "
United States
Nayeli A.
The price is €192
includes taxes & fees
29 Jun - 30 Jun
Master qtr close to nature & easy urban facilities

1BR 1BA Windy City Hideout

1BR 1BA Windy City Hideout
Belmont Cragin
1BR 1BA Windy City Hideout

Cozy 1BR in Walkable Area

Cozy 1BR in Walkable Area
Lincoln Square
9.8 out of 10, Exceptional, (14 reviews)
"Spotless, great location, would definitely stay again!"
United States
Debbie G.
The price is €184
includes taxes & fees
9 Jun - 10 Jun
Cozy 1BR in Walkable Area

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
North Center
9.6 out of 10, Exceptional, (77 reviews)
"Great location for a short trip "
United States
Eric W.
The price is €319
includes taxes & fees
8 Jun - 9 Jun
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

Apartment Attached to a 1900 historic Farm house

Apartment Attached to a 1900 historic Farm house
Old Mill Creek
8.6 out of 10, Excellent, (18 reviews)
"The place is very cozy and inviting. There was a smell we thought might have been cat urine on a blanket. Otherwise I'd recommend it."
United States
Matt H.
The price is €211
includes taxes & fees
11 Jun - 12 Jun
Apartment Attached to a 1900 historic Farm house

Skokie 1BR Stay Near Parks, Dining & Transit

Skokie 1BR Stay Near Parks, Dining & Transit
Skokie
Skokie 1BR Stay Near Parks, Dining & Transit

Cozy Studio in Portage Park

Cozy Studio in Portage Park
Portage Park
The price is €158
includes taxes & fees
7 Jun - 8 Jun
Cozy Studio in Portage Park

Chic, Quiet 1BR Near Dining Options– Perfect for 2

Chic, Quiet 1BR Near Dining Options– Perfect for 2
Avondale
7.4 out of 10, Good, (3 reviews)
"It was a very nice place for either one or two guests to stay. The video on the lock box was very helpful. Make sure guests know it takes about 10 minutes for the hot water to warm up. I knew that in advance, so it was no problem."
United States
ronald b.
Chic, Quiet 1BR Near Dining Options– Perfect for 2
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, apart-hotels, 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 €177 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?

Pleasant 3-bedroom house with occupied basement separate entrance.: 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 Six Flags Great America, or get outside and enjoy nature at Rosewood Beach. 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.