Photo by Tara Jabbari

Highwood Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Highwood

Sleeps 24+ Luxury house Near Chicago 12 king beds

Des Plaines
10.0 out of 10, Exceptional, (1)
"The house was amazing, and the host was very responsive and clear with communication! We will definitely be considering coming back here in the future!"
United States
Amiah S.
The price is NZ$11,752
includes taxes & fees
24 Nov - 25 Nov
Sleeps 24+ Luxury house Near Chicago 12 king beds

Breathtaking 2BR Near Lake Michigan in Evanston

South Evanston
9.4 out of 10, Exceptional, (3)
"The apartment was cool and was on central heat from the building. Shopping near by was great. the only negative was the street parking on a very busy street and no assigned parking spot. Once parked you did not want to move your vehicle because you would not get the spot back."
United States
Robert R.
Breathtaking 2BR Near Lake Michigan in Evanston

Montrose Studio:Your Uptown Base

Uptown
9.8 out of 10, Exceptional, (7)
"The property was exactly as pictured. The area was safe, had restaurants and coffee shops within a short walk. "
United States
Jamie
Montrose Studio:Your Uptown Base

1BR Pad with Homey Feel

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 NZ$317
includes taxes & fees
18 Nov - 19 Nov
1BR Pad with Homey Feel

Stunning & Stylish Downtown Studio - Highland Park

2.0 star property
Highland Park
8.8 out of 10, Excellent, (6)
"Everything was as described. Parking is secure. Location is quiet, inside a nice neighborhood "
United States
Alissa S.
The price is NZ$289
includes taxes & fees
13 Nov - 14 Nov
Stunning & Stylish Downtown Studio - Highland Park

1BR Chic & Sunny Place

Lincoln Square
9.6 out of 10, Exceptional, (4)
"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. "
United States
teresa G.
The price is NZ$317
includes taxes & fees
13 Nov - 14 Nov
1BR Chic & Sunny Place

Charming 1BR Apt in Evanston

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.
Charming 1BR Apt in Evanston

Great Layout – Spacious 2BR Apt

Rogers Park
10.0 out of 10, Exceptional, (4)
"Not to far from food spots and bars etc. most things we had interests in were 15-20 mins away so we Ubered a lot. No parking but we used the parking garage on the next block "
United States
Kijana W.
The price is NZ$372
includes taxes & fees
25 Nov - 26 Nov
Great Layout – Spacious 2BR Apt

Special Skevanston Space 2mi to Northwestern University & beach

Evanston
9.0 out of 10, Wonderful, (21)
"Was super smooth and easy, property was clean as could be and communication was excellent!"
United States
Mitchell M.
The price is NZ$397
includes taxes & fees
1 Dec - 2 Dec
Special Skevanston Space 2mi to Northwestern University & beach

Value Stay: Home - 2 Bedrooms

2.0 star property
Waukegan
10.0 out of 10, Exceptional, (2)
"The host was so amazing! Made many accommodations to make my stay very enjoyable! The host was very responsive and available. I would recommend this home on Vrbo to anyone having to go to Great Lakes Illinois. I was able to attend my son’s Navy graduation which wasn’t far from this location. Great stay! "
United States
You Tha Truth B.
The price is NZ$429
includes taxes & fees
13 Nov - 14 Nov
Value Stay: Home - 2 Bedrooms

Nice 1BR Spot, Unwind & Relax

Ravenswood
9.8 out of 10, Exceptional, (19)
"Great stay"
United States
Kayla K.
The price is NZ$310
includes taxes & fees
2 Dec - 3 Dec
Nice 1BR Spot, Unwind & Relax

1BR Homey Apt in Irving Park

Irving Park
10.0 out of 10, Exceptional, (2)
"It was wonderful and wil stay agian"
United States
Crystal P.
The price is NZ$392
includes taxes & fees
4 Dec - 5 Dec
1BR Homey Apt in Irving Park

Getaway Near ORD With Great Local Amenities

Des Plaines
9.0 out of 10, Wonderful, (4)
"It's hard get all this for this price. It's not that quiet like other reviews said unless you get up early in the morning. Heating works perfect, it is a bit warmer on the top floor and cooler in the kitchen but nothing to worry about. Parking on the front, walking distance to the grocery stores. 5 stars from me and will come back again."
United States
Dorde U.
The price is NZ$492
includes taxes & fees
19 Nov - 20 Nov
Getaway Near ORD With Great Local Amenities

Trendy & Comfy Studio Unit

Portage Park
9.4 out of 10, Exceptional, (3)
"Bathroom wasn’t as clean as it should be for guests. This is a 2nd floor unit, with an extremely steep staircase, which makes getting luggage up difficult. "
United States
Adriana J.
The price is NZ$293
includes taxes & fees
19 Nov - 20 Nov
Trendy & Comfy Studio Unit

Cozy 3BR Gem in North Center

North Center
9.2 out of 10, Wonderful, (7)
The price is NZ$593
includes taxes & fees
25 Nov - 26 Nov
Cozy 3BR Gem in North Center

Warm & Stylish 2BR Apt

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 NZ$356
includes taxes & fees
2 Dec - 3 Dec
Warm & Stylish 2BR Apt

Cozy & Inviting 2BR Apartment

Albany Park
10.0 out of 10, Exceptional, (1)
The price is NZ$356
includes taxes & fees
1 Dec - 2 Dec
Cozy & Inviting 2BR Apartment

Comfortable 2BR Chicago Apt

Albany Park
9.6 out of 10, Exceptional, (4)
"Kristine was helpful and provided information to my questions. I appreciated the cleanliness of the unit, since the building's hallways were dirty. It was a really hot weekend, so the AC window unit was struggling to keep up in the living room area. Thankfully, the bedrooms had its own AC window unit. We kept the bedroom doors closed, which helped for a more comfortable sleep. "
United States
asia c.
The price is NZ$406
includes taxes & fees
25 Nov - 26 Nov
Comfortable 2BR Chicago Apt

Homey 2BR Apt w/ Parking

Portage Park
10.0 out of 10, Exceptional, (4)
"The location was ideal for us and had a grocery store, a Starbucks and CVS close by . The neighborhood was safe for walking around . Beds comfortable and whole place was very clean . I would stay here again . "
United States
Sharlene T.
The price is NZ$364
includes taxes & fees
11 Dec - 12 Dec
Homey 2BR Apt w/ Parking

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

Uptown
8.8 out of 10, Excellent, (18)
"We had a great stay at this property! The space was clean, comfortable, and the location was perfect for the things we wanted to do. You're a quick walk to the red line train, which we utilized several times for exploring the city. Wrigley Field is also walkable if you are up for it! It's a great way to check out the surrounding neighborhoods. Highly recommend having breakfast at least once at Golden House Restaurant & Pancake House - we went twice because of it's convenience and quality....
United States
Christie C.
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
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.
Save an average of 15% on thousands of hotels when you're signed in

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 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 NZ$262 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?

Great 3 bedroom rental unit near Logan Square: This holiday home rental outside of Highwood is located on a lake, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, 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 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.