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Compare 317 Vacation Homes in Highwood with updated reviews, rates, and availability.

Great 3 bedroom rental unit near Logan Square

9.4 out of 10, Exceptional, (30)
"This is a really cute property close to a lot of neighborhood restaurants and bars. The host is really nice and even moved his car for us so we could have his spot when we arrived. We would definitely stay here again. "
Great 3 bedroom rental unit near Logan Square

Modern 3Bd Townhome Near Beach & Base

9.8 out of 10, Exceptional, (19)
"This property was exactly what we were needing! Cute house, very well maintained and the leasing agents were responsive to any concerns. "
Modern 3Bd Townhome Near Beach & Base

BoHo House - A Chic, 1903 Chicago Workers Cottage

10.0 out of 10, Exceptional, (10)
"Well located, comfortable and stylish home. The backyard was great to let the dog out and would be a fabulous place to hang out in warmer weather. Perfectly clean throughout, and great host communication made for a wonderful stay."
BoHo House - A Chic, 1903 Chicago Workers Cottage

Family frndly TwnHm by navy base

2.0 star property
9.6 out of 10, Exceptional, (12)
"Location was so close to Great Lakes book camp. 10 min or less. House was great and homey. "
Family frndly TwnHm by navy base

Riverfront Libertyville Retreat w/ Outdoor Kitchen

8.8 out of 10, Excellent, (24)
"The house was so cozy and Fun. Perfect space for our family gathering and less then 15 minutes form the Navy base. Our guest host Coco was so great and personable. "
Riverfront Libertyville Retreat w/ Outdoor Kitchen

Single Family home in Schaumburg, IL 3 bed/ 2 full baths/ fully fenced backyard

9.6 out of 10, Exceptional, (20)
"We have 3 kids and a dog and needed a clean, safe, spacious home to hang out and relax in while visiting family and this had everything we were looking for! I had to work during our stay so the desk in one of the bedrooms was perfect while the rest of the family could watch tv and play in the other areas of the house/yard. The owner was friendly and responsive and made sure we were taken care of. We plan on coming back any time we are in the area!"
Single Family home in Schaumburg, IL 3 bed/ 2 full baths/ fully fenced backyard

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

9.2 out of 10, Wonderful, (23)
"Is about 2 miles from great lakes for graduation. Layout is different. Sleeps 11 seats 5 or 6 in the living room, big table...half bath in kitchen...is cold in the winter...have to park in the back...walk around to front.can parknon the street but not overnight. The main bathroom with tyb sbower is high but has handrail. It snowed while we were there...owner shoveled sidewalk once. Overall it suit our need..its not high end but it was nice. Plenty of towels...no wash clothes...clean.."
New Your Home Away From Home! - Near Great Lakes Naval Base!!

Urban Farmhouse near O’Hare Airport

9.2 out of 10, Wonderful, (38)
"We loved having dedicated parking and the old farmhouse worked perfect for our group. We didn’t spend a lot of time at the house but it was easy to get to the sightseeing we wanted to do, the house was clean, check in and out were super easy, host was VERY easy to communicate with and provided great information very quickly! Everything was clean and we had all we needed and beds were comfortable. Really great for our group!"
Urban Farmhouse near O’Hare Airport

Your Next Vacation Home

9.6 out of 10, Exceptional, (37)
"It was just what we needed. Four friends in the city for an overnight stay. "
The price is SAR 900
SAR 1,455 total
includes taxes & fees
21 May - 22 May
Your Next Vacation Home

Beautiful 5 bedroom home on private lake

8.0 out of 10, Very Good, (1)
Beautiful 5 bedroom home on private lake

Comforting Retreat Near Woodfield Mall by RedAwning

9.6 out of 10, Exceptional, (14)
"My family and I had a wonderful time in Chicago and would definitely come back to visit this wonderful city and property. Our Communication with the property manager was not only appreciated but he was understanding and respectful. We had a few requests and not only did he meet them but delivered them personally. The home was comfortable and in a safe comfortable community. We were in access of everything needed or a short drive away. We thank you for having us !"
Comforting Retreat Near Woodfield Mall by RedAwning

4 Bedroom, 2 Full Bath. Centrally Located. Near O'Hare Airport and attractions

9.4 out of 10, Exceptional, (10)
"This house was great for what we needed! We were in town visiting family and the location was less than a mile from everything! The house was clean. The beds were comfortable and the kitchen was well stocked. I would recommend this house if you are headed to the suburbs of Chicago. "
4 Bedroom, 2 Full Bath. Centrally Located. Near O'Hare Airport and attractions

Entire 3 Bedroom Cozy Unit

9.2 out of 10, Wonderful, (12)
"This stay was perfect "
The price is SAR 701
SAR 1,152 total
includes taxes & fees
13 May - 14 May
Entire 3 Bedroom Cozy Unit

Breathtaking home close to Schaumburg, Chicago

9.8 out of 10, Exceptional, (53)
"Great home for a weekend in Palatine with family dinner. There's plenty of space to spread out and connect with family. The dining room was spacious and comfortable. We enjoyed our stay immensely "
Breathtaking home close to Schaumburg, Chicago

Entire Lake Villa Home!

9.4 out of 10, Exceptional, (37)
"We stayed over the weekend to attend family events. The location is very near where we needed it to be. If you are here to go to Six Flags or Great Lakes Naval Base. You should be good as it’s about 20 minutes out. Quiet neighborhood"
Entire Lake Villa Home!

Lake/Beach Getaway (Remodeled)

9.8 out of 10, Exceptional, (30)
"Loved the view of the lake out the big front window. Perfect place for a family getaway. Apple play on tv worked great. We set up 5 yoga mats in living room and did yoga. Great full length mirror. Cute decor. Couch was comfy and bigger than I thought it would be from the pics. Wish the bunk bed had comfier mattresses - our teen girls were complaining - but they’ll survive lol! Bring coffee for standard coffee maker if you drink coffee. And have fun! Can’t wait to go back this summer. :) "
The price is SAR 563
SAR 1,024 total
includes taxes & fees
28 Apr - 29 Apr
Lake/Beach Getaway (Remodeled)

The Sunset Manor - Luxe Mansion for Serene retreat

2.0 star property
9.0 out of 10, Wonderful, (2)
"We needed an ample space to stay for an event we were organizing in the area. It served its purpose in this regard. The owner has done a great job creating an inviting space in an older home. The rooms are quite dark, and the bathroom lighting is less than ideal for getting ready. The master bath mirror light did not work and could not be replaced while we were there. Our group wanted to play ping pong and air hockey, and there were no balls or pucks for the table. The heating in the house is...
The price is SAR 2,134
SAR 3,938 total
includes taxes & fees
27 Apr - 28 Apr
The Sunset Manor - Luxe Mansion for Serene retreat

Gurnee Getaway: Modern Oasis Near Six Flags & Naval Base!

9.8 out of 10, Exceptional, (10)
"Our family came to visit for our son's Navy Bootcamp Graduation. This house was very comfortable. There were plenty of spaces to relax & visit with each other. The house was well equipped. The host was extremely helpful & friendly. We highly recommend this home!"
Gurnee Getaway: Modern Oasis Near Six Flags & Naval Base!

Home in DT Libertyville near Corp HQs & Naval Base

9.6 out of 10, Exceptional, (11)
"We really enjoyed our stay here. I highly recommend it. "
Home in DT Libertyville near Corp HQs & Naval Base

Quaint Bungalow, near Great Lakes Naval Base

9.8 out of 10, Exceptional, (60)
"Home is an older home but redone nice. Since it is an older home the floors squeak a lot when walking on them. The heat was hard to regulate since it’s the old radiator heat but once it gets warm you will be toasty. The half bath in the basement isn’t appealing since the basement leading to it is old and dreary looking. The bath upstairs is really nice. The backyard is nice. "
The price is SAR 413
SAR 1,058 total
includes taxes & fees
27 Apr - 28 Apr
Quaint Bungalow, near Great Lakes Naval Base
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 property types in Highwood

2-bedroom apartment just 2 minutes drive to Wrigley Field

2.0 star property
9.8 out of 10, Exceptional, (11)
"It was such an amazing property. Short walk to Wrigley which was perfect for me and my friends!!!!!! Will be booking again in the future"
The price is SAR 334
SAR 919 total
includes taxes & fees
30 Apr - 1 May
2-bedroom apartment just 2 minutes drive to Wrigley Field

Bright Garden Studio

9.0 out of 10, Wonderful, (21)
"Great Location"
The price is SAR 300
SAR 873 total
includes taxes & fees
29 Apr - 30 Apr
Bright Garden Studio

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

10.0 out of 10, Exceptional, (173)
"Well equipped APT on quiet streetOn street parking was no problemNice new appliancesBeds comfortableLinens niceGreat trip!Thank you!"
Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field
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.