Photo by Tara Jabbari

Search Holiday Rentals in Highwood

    price find illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Save instantly and earn perks with One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Top Holiday Rentals in Highwood

Our top choices for Highwood holiday rentals

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (86)
"Super nice hotel and staff "
The price is £170
includes taxes & fees
2 Sept - 3 Sept
The Gem Museum Suites

Relaxing Chicago Studio

10.0 out of 10, Exceptional, (8)
"Had a great stay. Great location. "
The price is £154
includes taxes & fees
16 Sept - 17 Sept
Relaxing Chicago Studio

Nice 1BR Spot, Unwind & Relax

10.0 out of 10, Exceptional, (14)
"Super clean. Cozy. SAFE. Short drive to nearly every big attraction! Host was very communicative and kind!!"
The price is £147
includes taxes & fees
2 Sept - 3 Sept
Nice 1BR Spot, Unwind & Relax

Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater

6.0 out of 10, (2)
"Great space for large groups. Park across the street is a great "feature"."
The price is £691
includes taxes & fees
23 Sept - 24 Sept
Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater

Uptown Studio Gem Sum

7.0 out of 10, Good, (4)
"This studio is very clean and is located in a neighborhood with access to anything you would want to do or see. The stairway and halls are not pristine, but studio is good. Neighbors were quiet and seldom seen during my stay. Excellent restaurant right across the street and grocery nearby. Wrigley Field is easy walk. Check in was confusing for me, but it worked out. "
The price is £146
includes taxes & fees
1 Sept - 2 Sept
Uptown Studio Gem Sum

Prime City Stay in a 1BR Apt

9.2 out of 10, Wonderful, (9)
The price is £147
includes taxes & fees
9 Sept - 10 Sept
Prime City Stay in a 1BR Apt

Homey 1BR Space Apartment

9.0 out of 10, Wonderful, (4)
"Great location. Very walkable to restaurants and bars. Awesome park nearby. Host was easy to communicate with. "
The price is £147
includes taxes & fees
9 Sept - 10 Sept
Homey 1BR Space Apartment

Central Haven Escape: Stylish 3BR With Free Parking

6.8 out of 10, (6)
"The overall experience was surprisingly great. We were a little worried after reading some bad reviews because of the house smelling like smoke. It didn’t. In fact, it smelled super clean and fresh. It is a cute little, older, clean 3 bedroom apartment above a building in a downtown neighborhood. So cute!"
Central Haven Escape: Stylish 3BR With Free Parking

Cozy studio in Andersonville Chicago

9.2 out of 10, Wonderful, (23)
"It was a great location, internet was a little spotty on streaming services but we were in walking distance to so much it was worth it "
The price is £122
includes taxes & fees
2 Sept - 3 Sept
Cozy studio in Andersonville Chicago

Luxurious 3 Bedroom Apartment in Chicago

9.2 out of 10, Wonderful, (23)
"Great property! Would visit again!"
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, (39)
"Great place to stay when you’re in town for the Cubbies! "
The price is £250
includes taxes & fees
2 Sept - 3 Sept
2-bedroom apartment just 2 minutes drive to Wrigley Field

Huge Projector and Designated Workspace - Near Wrigley!

The price is £233
includes taxes & fees
1 Sept - 2 Sept
Huge Projector and Designated Workspace - Near Wrigley!

Chic apartment with fitness room and AC in beautiful Chicago

7.0 out of 10, Good, (2)
"This was a nice apartment and stay forThe price. Close to train station. However would be nice to add a microwave. I had to reach out by calling the host after no response about check in information on VRBO app. Received the check in information very late the night prior to my stay. Was charged 50 for early check in but when we arrived they were stillCleaning and we had to wait about 15-20minutes outside. Overall with all the inconveniences. It ended up being good stay for the price. "
The price is £169
includes taxes & fees
28 Aug - 29 Aug
Chic apartment with fitness room and AC in beautiful Chicago

4BR Retreat w/ Theater, Game Room & Backyard

8.0 out of 10, Very good, (8)
The price is £379
includes taxes & fees
23 Sept - 24 Sept
4BR Retreat w/ Theater, Game Room & Backyard

North Chi Retreat-Near Navel base-Sauna,Pool, Airhokey, grill,King bed,Tikki Bar

9.6 out of 10, Exceptional, (4)
"Home was cute and as advertised, outdoor area great for families to relax. Only recommendation to have some information at the home for guests in the event the alarm system is activated so it can be acknowledged quickly. "
North Chi Retreat-Near Navel base-Sauna,Pool, Airhokey, grill,King bed,Tikki Bar

Charming 3-bedroom house in Grayslake

9.8 out of 10, Exceptional, (15)
"The house, yard and location were all perfect. "
The price is £412
includes taxes & fees
1 Sept - 2 Sept
Charming 3-bedroom house in Grayslake

Great 3 bedroom rental unit near Logan Square

9.6 out of 10, Exceptional, (53)
"Cozy place to stay with a VERY QUICK response from host. Great location in quiet neighborhood. I would stay here again in a heartbeat. "
Great 3 bedroom rental unit near Logan Square

Riverfront Libertyville Retreat w/ Outdoor Kitchen

8.6 out of 10, Excellent, (30)
"Thank you very much"
Riverfront Libertyville Retreat w/ Outdoor Kitchen

Charming Wrigleyville Home Close to the Cubs!

9.4 out of 10, Exceptional, (31)
"Great stay"
Charming Wrigleyville Home Close to the Cubs!

Cozy unit steps from Loyola Uni with AC, WiFi, fitness room and big TV

9.0 out of 10, Wonderful, (6)
"This property is average and worked ok for a short weekend when we just slept there. "
Cozy unit steps from Loyola Uni with AC, WiFi, fitness room and big TV
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

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 £122 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?

Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater: This holiday home rental outside of Highwood is equipped with a selection of games, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 8 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.