Photo by Tara Jabbari

Highwood Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Highwood

Property grounds
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
9.2 out of 10, Wonderful, (9)
"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 NZ$365
includes taxes & fees
28 May - 29 May
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
Private kitchen
Your Next Vacation Home
10.0 out of 10, Exceptional, (10)
"This home was very Beautiful and More Spacious than expected with a Beautiful back yard that we sadly didn’t get to enjoy because of the rain. The house location was great with A lot of stores and restaurants nearby. Next time we have a Family gathering I definitely will be rebooking"
The price is NZ$556
includes taxes & fees
3 Jun - 4 Jun
Your Next Vacation Home
Exterior
Breathtaking home close to Schaumburg, Chicago
9.8 out of 10, Exceptional, (37)
"It was a perfect location and plenty of space for family of 8 plus visiting friends. Mike was a great host and we got to enjoy some firewood he had set up for us to have a fire. Highly recommend! The description says 4 bathrooms and there are 3 bathrooms…the only discrepancy."
Breathtaking home close to Schaumburg, Chicago
Save an average of 15% on thousands of hotels when you're signed in
Interior
Bright Garden Studio
9.0 out of 10, Wonderful, (4)
"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
Fridge, microwave, oven, stovetop
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
9.2 out of 10, Wonderful, (15)
"we were a group of seven, aged 18 months to 66 years. the flat was great. with the three bedrooms, queen beds in two rooms, two twins in the other, plus a pack’n play for the youngest, everyone had a comfortable place to sleep. also great that we were able to make breakfast in the mornings! the neighborhood was fantastic! very friendly people, so quiet, plenty of on street parking (no permits required!!!) easy communication with the host. great price! we appreciated the welcome booklet. flat was...
The price is NZ$893
includes taxes & fees
3 Jun - 4 Jun
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
Smart TV, stereo
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
9.6 out of 10, Exceptional, (8)
"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 NZ$389
includes taxes & fees
3 Jun - 4 Jun
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Beach nearby
Pet-Friendly Urban Chicago Vacation Rental Condo
9.8 out of 10, Exceptional, (6)
"Great and very clean place for our daughter’s graduation week."
Pet-Friendly Urban Chicago Vacation Rental Condo
Terrace/patio
Roxan Corner
9.0 out of 10, Wonderful, (18)
"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
Exterior
Epic Lake Views Await You - You Will WANT to Wake up Early for the Sunrise by RedAwning
8.6 out of 10, Excellent, (15)
"Place was clean and beds were great. Very nice kitchen and being in the water is neat. The location is perfect for someone who doesn’t care if it’s off the beaten path a little. Parking is tough after 8pm. That would be my only complaint."
Epic Lake Views Await You - You Will WANT to Wake up Early for the Sunrise by RedAwning
Fridge, microwave, oven, dishwasher
PET FRIENDLY! Unique Converted Storefront Stay - Great Neighborhood! by RedAwning
9.6 out of 10, Exceptional, (19)
"Close to everything"
PET FRIENDLY! Unique Converted Storefront Stay - Great Neighborhood! by RedAwning
Exterior
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, (157)
"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,
Microwave
Charming Wrigleyville Home Close to the Cubs!
8.8 out of 10, Excellent, (5)
"Location, location, and location GREAT Couple of blocks from Wrigley field. There was no place to sit and have a conversation or eat. A small table with chairs would be nice. Since there is no table it would have been nice to have a TV in both bedrooms. The bathroom is so spacious and the shower is wonderful. We loved it. We have give the information to several of of friends to use"
Charming Wrigleyville Home Close to the Cubs!
Fridge, microwave, oven, stovetop
Luxe Haus of Love—Renovated 1938 Cape Cod |Heated FLRS |420+
10.0 out of 10, Exceptional, (12)
"We loved staying at this property. We always opt for VRBO and other home rentals when we travel and I always do extensive research on each property/neighborhood before I book. This property ranks as one of our top experiences and we've traveled all over the world. The home itself is lavishly renovated and comfortably appointed. TONS of sleeping options, many sparklingly clean bathrooms, two dining areas, two sitting areas, a lovely (and quiet) backyard, and an impressive kitchen all with...
The price is NZ$1,492
includes taxes & fees
2 Jun - 3 Jun
Luxe Haus of Love—Renovated 1938 Cape Cod |Heated FLRS |420+
Interior
Light Filled with Tasteful Pops of Color - You Will Love This Mid-Century Modern Gem by RedAwning
10.0 out of 10, Exceptional, (9)
"Pictures are exactly as reality. Very spacious 3bdrm priced fairly. Excellent location (not in the HEART of action but close enough)- walking distance to El, coffee shop, restaurants, breweries and boutiques. City parking. Would suggest to others looking for clean, basic yet not junky 3 bedroom! A note to owner: the ship is not needed on the mantle :) we moved as soon as we opened the door! Let that beautiful fireplace shine! Would"
Light Filled with Tasteful Pops of Color - You Will Love This Mid-Century Modern Gem by RedAwning
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, (56)
"We were very impressed. A very clean beautiful home. Had all the convenience of home. I definitely would recommend staying here. I give 5plus stars"
3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY
Private kitchen
Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field
10.0 out of 10, Exceptional, (146)
"Kim’s place is in a quiet neighborhood, just a couple blocks from the Roscoe Village shops and restaurants. It was also an easy 20 minute walk from shops and restaurants in the Southport area and a 30 minute walk from Wrigley Field. We had no problems parking on the street throughout our stay. If you enjoy Cubs games and a variety of restaurants and shops, all within walking distance…then this is the place for you!"
Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field
Property grounds
The Lake House-2br/2bth - 50 steps from the beach!
10.0 out of 10, Exceptional, (20)
"This apartment was perfect for visiting our daughter at Loyola University. Very close to campus, transportation and food. The apartment was clean and had everything we needed. We would stay again!"
The Lake House-2br/2bth - 50 steps from the beach!
Exterior
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, (178)
"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,
Smart TV
Chic, Cozy home, by Blue Line Train Stop + Free parking
9.6 out of 10, Exceptional, (24)
"Close to blue line CTA. Quiet. Parking on street."
Chic, Cozy home, by Blue Line Train Stop + Free parking
TV
New Your Home Away From Home! - Near Great Lakes Naval Base!!
9.4 out of 10, Exceptional, (11)
"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!!
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

Terrace/patio
Hilton Chicago O'Hare Airport
4.0 star property
7.6 out of 10, Good, (1975)
"Convenient "
The price is NZ$367
includes taxes & fees
21 Jun - 22 Jun
Hilton Chicago O'Hare Airport
Lobby
Best Western At O'Hare
2.5 star property
7.4 out of 10, Good, (1862)
"It is a nice hotel with a very cooperative staff"
The price is NZ$203
includes taxes & fees
28 May - 29 May
Best Western At O'Hare
Indoor pool, outdoor pool
Marriott Chicago O'Hare
3.5 star property
8.2 out of 10, Very good, (1014)
"Wallpaper was peeling from the wall. Bathroom was tiny. No valet. "
The price is NZ$324
includes taxes & fees
14 Jun - 15 Jun
Marriott Chicago O'Hare
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Highwood holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Highwood. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Highwood. Seeing all the best attractions is bound to make you fall in love with Highwood. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Highwood short-term rentals, that won’t be hard to do.

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?

Your Next Vacation Home: This holiday home rental outside of Highwood has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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 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.

Recent reviews of Highwood properties
Expedia verified reviews