Photo by Tara Jabbari

Holiday Rentals in Highwood

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Holiday Rentals in Highwood

Great 3 bedroom rental unit near Logan Square

9.4 out of 10, Exceptional, (23)
"Safe neighborhood and super responsive host. I would definitely book again."
Great 3 bedroom rental unit near Logan Square

Bright Garden Studio

8.8 out of 10, Excellent, (17)
"Great spot to stay, very accommodating and everything we needed! Will be back for future visits."
The price is €199
includes taxes & fees
17 Feb - 18 Feb
Bright Garden Studio

Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field

10.0 out of 10, Exceptional, (168)
"Hosts were responsive to our needs. Perfect location for our stay"
Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field

Charming Wrigleyville Home Close to the Cubs!

9.4 out of 10, Exceptional, (15)
"Great walkable location with easy access to everything. We appreciated the parking passes so much. Brian has a very nice set up eith ever3you need for a great weekend getaway. "
Charming Wrigleyville Home Close to the Cubs!

The Holiday Lake House - 2br 2bth - 50 steps from the beach!

10.0 out of 10, Exceptional, (39)
"This was a great place to celebrate the holidays. Kitchen was well stocked with cookware and utensils to make Christmas dinner and we had plenty of room to gather for game night. Beds were comfy and all amenities were in good condition. The apartment looks brand new! Loved the shampoo/conditioner/soap dispensers in the shower! Will definitely be back next Christmas. Thanks for the hospitality!"
The Holiday Lake House - 2br 2bth - 50 steps from the beach!

Quaint Bungalow, near Great Lakes Naval Base

10.0 out of 10, Exceptional, (56)
"Got to stay in this wonderful home while visiting my son and his family. I loved it!"
The price is €302
includes taxes & fees
23 Feb - 24 Feb
Quaint Bungalow, near Great Lakes Naval Base

2-bedroom apartment just 2 minutes drive to Wrigley Field

2.0 star property
9.6 out of 10, Exceptional, (5)
"One of the most beautiful rentals I've stayed in. Also, when there was a hiccup in the booking process, the owner communicated directly with me right away, coming to a solution that made everyone happy. A very lovely experience all around. "
The price is €287
includes taxes & fees
17 Feb - 18 Feb
2-bedroom apartment just 2 minutes drive to Wrigley Field

Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!

4.0 star property
9.4 out of 10, Exceptional, (38)
"Numerous problems that owner tried to fix-no wi-fi, no ac, broken upstairs dishwasher, basement flooded when we used downstairs washing machine. Place had not been cleaned prior to check in, trash sack in entry way, litter on floor, mop on back steps. Great location."
Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!

Beautiful 5 bedroom home on private lake

Beautiful 5 bedroom home on private lake

Your Next Vacation Home

9.8 out of 10, Exceptional, (31)
"Very clean, extremely nice home. "
The price is €303
includes taxes & fees
3 Mar - 4 Mar
Your Next Vacation Home

Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!

10.0 out of 10, Exceptional, (123)
"Spacious inside, 9 bedrooms, very warm in a cold month. Good location to walk, close to public transit and ample parking - squeezed in 5 vehicles. Owner contact and responses excellent."
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!

Walking distance to restaurants, shops and Lake Michigan,

9.6 out of 10, Exceptional, (175)
"We were very pleased with the property. Stayed there over the Thanksgiving holiday & weekend while visiting my older daughter. Nice neighborhood & easy location to get to other parts of the city. Everything was as depicted in the description and communication with management was excellent. Would stay here again."
Walking distance to restaurants, shops and Lake Michigan,

New Your Home Away From Home! - Near Great Lakes Naval Base!!

9.4 out of 10, Exceptional, (20)
"This was my first booking with VRBO, we were in Chicago for my niece's Navy graduation. Sam, the host, was extremely communicative. I had sent him a question in the inbox and he called me within 3 minutes. The property is spacious, only 4 minutes from base and very close to a multitude of restaurants. Very clean, kitchen was not lacking in glasses / plates / accessories. We had a wonderful stay and I highly recommend Sam's house. Thank you again, Sam!!"
New Your Home Away From Home! - Near Great Lakes Naval Base!!

Chic, Cozy home, by Blue Line Train Stop + Free parking

9.4 out of 10, Exceptional, (43)
"Just as described and fit our needs perfectly. Super clean"
Chic, Cozy home, by Blue Line Train Stop + Free parking

Master qtr close to nature & easy urban facilities

9.8 out of 10, Exceptional, (47)
"This place was amazing!! The bed was super comfortable and the jet tub was out of this world!! It was very clean and quiet. The host was very accomodating and had great communication. My husband and stayed overnight because he had an army function to attend. This was perfects! to attend. "
The price is €189
includes taxes & fees
17 Feb - 18 Feb
Master qtr close to nature & easy urban facilities

100 Yr. Old Chicago Brick Craftsman with yard, Near Beach and Loyola!

10.0 out of 10, Exceptional, (19)
"This was the perfect place while we were in town for a family event. The apartment was so welcoming! The kids felt right at home and loved exploring every inch, and even put on a dance party using the instruments that were there (but not too loud-I promise!). There was enough room for their grandmother to stay as well, and everyone had plenty of space to relax. The communication was excellent as well! We appreciated all the hospitality! "
100 Yr. Old Chicago Brick Craftsman with yard, Near Beach and Loyola!

Chic apartment in phenomenal Chicago with WiFi, AC

8.8 out of 10, Excellent, (6)
"I was really impressed with the decor and layout. The TV wasn’t working but other than that the experience was great"
Chic apartment in phenomenal Chicago with WiFi, AC

GORGEOUS 4/2.5 GREYSTONE HOME | WRIGLEY

8.4 out of 10, Very good, (25)
"We booked this location for our large family of 8. Clean and it slept all of us well, with plenty of space to wind down and hang out after a day seeing the sights in the city. Easy walking distance to Wrigley field and local attractions. Short drive into the city or hop on the train a block away. Seemed like a safe neighborhood and has a garage for parking. (Note a Suburban is too long to park inside and still close the door)Good communication with property owner/management. We will...
GORGEOUS 4/2.5 GREYSTONE HOME | WRIGLEY

Eddy House, Roscoe Village Hideaway

10.0 out of 10, Exceptional, (5)
"Great house . "
Eddy House, Roscoe Village Hideaway

NEW, clean & sunny, 2bd, private deck, 15min to Wrigley!

10.0 out of 10, Exceptional, (1)
"First of all, the pictures does not do this place justice. It was so bright and sunny and well decorated. It was WELL stocked with anything you could think of. And our hostess was the mostess. Thank you again Tori for everything. I just loved the place! Easy parking as well, that's always a plus in my book!"
NEW, clean & sunny, 2bd, private deck, 15min to Wrigley!
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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Other types of properties in Highwood you may be interested in

Hyatt Regency Schaumburg Chicago

4.0 star property
8.4 out of 10, Very good, (1013)
"Pretty good service. 5 stars ⭐️ ⭐️⭐️⭐️⭐️"
The price is €96
includes taxes & fees
17 Feb - 18 Feb
Hyatt Regency Schaumburg Chicago

Hyatt Regency O'Hare Chicago

4.0 star property
8.6 out of 10, Excellent, (1286)
"Property was clean"
The price is €126
includes taxes & fees
18 Feb - 19 Feb
Hyatt Regency O'Hare Chicago

Hampton Inn Chicago-O'Hare International Airport

2.5 star property
9.2 out of 10, Wonderful, (1732)
"Efficient and friendly service."
The price is €97
includes taxes & fees
23 Feb - 24 Feb
Hampton Inn Chicago-O'Hare International 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.

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.