Photo by Tara Jabbari

Highwood Vacation Rentals

Vacation Rentals in Highwood

Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Smart TV, stereo
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
9.6 out of 10, Exceptional, 8 reviews
"The proximity to Great Lakes Recruitment Center, Sarge’s Meet & Greet, restaurants, etc. is perfect. We were in town for our son’s boot camp graduation and knew we wanted more room to hang out than a typical hotel room would offer. It was great to be able to relax, watch movies, just hang out with our sailor for the precious two days we had. This place has location, location, location if you’re coming in for boot camp graduation."
The price is $145
$263 total
includes taxes & fees
Jun 16 - Jun 17
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
Property grounds
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
9.2 out of 10, Wonderful, 9 reviews
"Great location with two master suites with king beds. Breakfast buffet was good. Next time I will request first floor as there is no elevator."
The price is $179
$227 total
includes taxes & fees
Jun 17 - Jun 18
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
Roxan Corner
Terrace/patio
Roxan Corner
9.0 out of 10, Wonderful, 18 reviews
"This duplex was perfect for my three sons and myself. We stayed five days to attend one of my son’s Navy Graduation! House was very clean and modern. Had everything we needed, was a nice neighborhood, quiet neighbors? Close to everywhere we needed to go. Only suggestion would be to have the owners secure the rugs, they are very slippery. "
Roxan Corner
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Great Amenities Onsite! Pool, Private Parking, Free Breakfast, Close to Legoland
Interior
Great Amenities Onsite! Pool, Private Parking, Free Breakfast, Close to Legoland
8.0 out of 10, Very Good, 2 reviews
"We enjoyed our stay with plenty of space for two couples. Separate bedrooms/baths were perfect. Furnature in the living room needs updating."
The price is $196
$248 total
includes taxes & fees
Jun 17 - Jun 18
Great Amenities Onsite! Pool, Private Parking, Free Breakfast, Close to Legoland
Walking distance to restaurants, shops and Lake Michigan,
Exterior
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, 179 reviews
"Beautiful and spacious unit with everything you could ask for. There were 5 of us and we had plenty of space to spread out and be comfortable. Great hospitality and Ross met us for checkin even though our flight had been delayed. Wonderful location and within walking distance of restaurants, shops and the CTA station (Howard). Would definitely stay again."
Walking distance to restaurants, shops and Lake Michigan,
Your Next Vacation Home
Private kitchen
Your Next Vacation Home
10.0 out of 10, Exceptional, 11 reviews
"Our stay was perfect for the few days we stayed for my niece's wedding. We enjoyed the house and its accommodations. Our host, Pervaiz was wonderful as well. I will definitely come back and refer my friends and family. Thank you, Jeanette!!"
The price is $215
$363 total
includes taxes & fees
Jun 10 - Jun 11
Your Next Vacation Home
Bright Garden Studio
Interior
Bright Garden Studio
9.0 out of 10, Wonderful, 4 reviews
"I'm a seminary student, and I came into town for an intensive class. So, I was really only in the space in the evenings, but it was comfy. The location is amazing!!! The studio apartment was decently clean. The projector is VERY cool. There were a few details I could not find instructions for, like where to take the garbage out when I was on my way out. But I left a message for the owner and they were good about it. I would stay again. Recommend."
Bright Garden Studio
The Lake House-2br/2bth - 50 steps from the beach!
Property grounds
The Lake House-2br/2bth - 50 steps from the beach!
10.0 out of 10, Exceptional, 20 reviews
"Home is lovely and resides just north of the L-Red Line so it was really easy to pop into downtown Chicago without issue! We stayed here with our three kids and it was a beautiful, well maintained rental! Additionally, the owner was a gem and very communicative!"
The Lake House-2br/2bth - 50 steps from the beach!
Walking distance to restaurants, shops and Lake Michigan,
Exterior
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, 157 reviews
"Great property and Ross is a wonderful host. Even recommended dinner spots Hope to stay here again"
Walking distance to restaurants, shops and Lake Michigan,
Breathtaking home close to Schaumburg, Chicago
Exterior
Breathtaking home close to Schaumburg, Chicago
9.8 out of 10, Exceptional, 38 reviews
"Our family had a wonderful experience! Fantastic location - safe and quiet neighborhood (feels very tucked away, we saw deer in the backyard and took peaceful walk/run around the area), close enough to walk to a restaurants/7-11, and close to the highway to travel in to the city! Great communication from Michael, very responsive. Layout was great for 3 families with spacious rooms, private bathrooms, and open layout. Very pleased with our visit!"
Breathtaking home close to Schaumburg, Chicago
Schaumburg Pool House
Outdoor pool, a heated pool
Schaumburg Pool House
9.8 out of 10, Exceptional, 6 reviews
"Great place and neighborhood, lots of restaurants and mall close by. Place was clean and conveniently located. We enjoyed our stay!"
Schaumburg Pool House
3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY
Fridge, microwave, oven, stovetop
3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY
10.0 out of 10, Exceptional, 57 reviews
"Thank you so much for the lovely stay. Although I was unable to attend, my husband, son, daughter, and son-in-law were able to stay. They all made mention of how clean everything was, how everything was comfortable and well appointed. It was easy to check in and check out. I think beds could have been a little bit softer (all four commented on that), but your place is beautiful! Would also recommend ceiling fans or floor fans in each room to cut out noise and for better temperature. Would...
3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
Fridge, microwave, oven, stovetop
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
9.4 out of 10, Exceptional, 16 reviews
"We came into town for my sisters wedding for the long weekend. Our stay was great, we had easy communication with Craig, and our needs were met quickly. Plenty of space for us to get ready and not be on top of each other which was awesome. The area is super nice, beautiful neighborhood, very family friendly with a 9 year old. Thank you so much for everything!"
The price is $269
$546 total
includes taxes & fees
Jun 10 - Jun 11
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
Chic, Cozy home, by Blue Line Train Stop + Free parking
Smart TV
Chic, Cozy home, by Blue Line Train Stop + Free parking
9.6 out of 10, Exceptional, 24 reviews
"Close to blue line CTA. Quiet. Parking on street."
Chic, Cozy home, by Blue Line Train Stop + Free parking
PET FRIENDLY! Unique Converted Storefront Stay - Great Neighborhood! by RedAwning
Fridge, microwave, oven, dishwasher
PET FRIENDLY! Unique Converted Storefront Stay - Great Neighborhood! by RedAwning
9.6 out of 10, Exceptional, 19 reviews
"Close to everything"
PET FRIENDLY! Unique Converted Storefront Stay - Great Neighborhood! by RedAwning
New Your Home Away From Home! - Near Great Lakes Naval Base!!
TV
New Your Home Away From Home! - Near Great Lakes Naval Base!!
9.4 out of 10, Exceptional, 11 reviews
"We really enjoyed the house, its very confortable, clean and the rooms are big. The house is very close to the base. Thanks."
New Your Home Away From Home! - Near Great Lakes Naval Base!!
Pets are welcome! Outdoor BBQ Grill, Near Independence Grove Dog Park!
Fridge, microwave, oven, stovetop
Pets are welcome! Outdoor BBQ Grill, Near Independence Grove Dog Park!
4.0 out of 10, 1 review
"I left early to get another hotel."
The price is $95
$125 total
includes taxes & fees
Jun 6 - Jun 7
Pets are welcome! Outdoor BBQ Grill, Near Independence Grove Dog Park!
Pet-Friendly Urban Chicago Vacation Rental Condo
Beach nearby
Pet-Friendly Urban Chicago Vacation Rental Condo
9.8 out of 10, Exceptional, 6 reviews
"Great and very clean place for our daughter’s graduation week."
Pet-Friendly Urban Chicago Vacation Rental Condo
Elegant 3 Bedroom and 1 Bath Apartment
Desk, iron/ironing board, free WiFi, bed sheets
Elegant 3 Bedroom and 1 Bath Apartment
9.0 out of 10, Wonderful, 2 reviews
"This was a very nice place for 6 people to stay. It was near enough to everything that it was easy to get to places. Parking on the street was an issue so be mindful that if you are looking to always park out front."
Elegant 3 Bedroom and 1 Bath Apartment
Family Townhome available - 2 Bedroom, 1.5 bath, tv, kitchen, appliances, I94
Exterior
Family Townhome available - 2 Bedroom, 1.5 bath, tv, kitchen, appliances, I94
8.0 out of 10, Very Good, 10 reviews
"I've rented 26 homes in three years since I started using short term rentals. This is the worst I've ever had. Starting with check-in. NOT mentioned in the ad is the fact that you have to download a separate app to open the doors. This is a full-on registration...email/phone/etc. Shouldn't be needed and now I'm already getting fresh new spam! Yay! House rules: Don't use laundry room, it's unsafe. Oh but if you need to clean something, go ahead and use the laundry! OK, now the house. I WISH I...
The price is $150
$244 total
includes taxes & fees
Jun 6 - Jun 7
Family Townhome available - 2 Bedroom, 1.5 bath, tv, kitchen, appliances, I94
Don't see what you're looking for?
See all available properties in Highwood
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.

Other types of properties in Highwood you may be interested in

Best Western At O'Hare
Lobby
Best Western At O'Hare
2.5 star property
7.4 out of 10, Good, 1,881 reviews
"Dirty carpet. Dead bedbug found."
The price is $110
$125 total
includes taxes & fees
Jun 30 - Jul 1
Best Western At O'Hare
Marriott Chicago O'Hare
Indoor pool, outdoor pool
Marriott Chicago O'Hare
3.5 star property
8.2 out of 10, Very Good, 1,015 reviews
"My children, and I stayed here recently, and this hotel is absolutely gorgeous!! & was very clean! The shrimp from their restaurant was delicious along with the quesadillas! "
The price is $159
$187 total
includes taxes & fees
Jul 1 - Jul 2
Marriott Chicago O'Hare
Hyatt Place Chicago/O'Hare Airport
Exterior
Hyatt Place Chicago/O'Hare Airport
3.0 star property
8.4 out of 10, Very Good, 2,327 reviews
"The staff were very friendly and helpful! Peaceful and quit atmosphere. "
The price is $131
$154 total
includes taxes & fees
Jun 26 - Jun 27
Hyatt Place Chicago/O'Hare Airport
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.

Everything you need to know about Highwood vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Highwood vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Highwood vacation 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 low season months. For more hustle and bustle, you may prefer to visit Highwood in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $95 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Highwood rentals

At Expedia, we put the best Highwood vacation 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 vacation.

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 vacation rentals in Highwood?

Yes, there are vacation rentals where you'll be just 12.7 mi (20.4 km) from Six Flags Great America, offering you a more remote option to escape the hustle and bustle. Highwood is known for its shopping and restaurants.

What are some of the best vacation home rentals that Highwood has to offer?

Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking: This vacation home rental near Highwood is located in the city center and offers a barbecue grill, air-conditioning, and cable TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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 Ravinia Park. In the larger area, you’ll find Naval Base Great Lakes and Lake Forest College.

What are vacation rentals like in Highwood?

Vacation rentals are private properties you can reserve for a short or long stay in Highwood. Vacation rentals offer extras such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for family trips.

Recent reviews of Highwood properties
Expedia verified reviews

Residence Inn by Marriott O'Hare

Residence Inn by Marriott O'Hare

5/5 Excellent
"We stayed here because we had a quick flight out of O’Hare the next day. There were different dining options and it was close to target everything was in walking distance"
A verified traveler stayed at Residence Inn by Marriott O'Hare
Posted 1 day ago
Residence Inn by Marriott O'Hare