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

Entire 3 Bedroom Cozy Unit

9.4 out of 10, Exceptional, (14)
"We traveled from STL for a concert at the Genesee Theatre and stayed for the night. We had some beers at a local tavern, ubered easily to and from the theatre, and had an authentic Mexican breakfast down the street. We prepared a late night snack in the equipped kitchen, slept late in our comfy beds, and were cozy warm. "
Entire 3 Bedroom Cozy Unit

Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families

9.0 out of 10, Wonderful, (30)
"Had fun"
The price is AED 545
AED 968 total
includes taxes & fees
8 Jun - 9 Jun
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families

Charming 3-bedroom townhome with AC and WiFi in Waukegan.

9.6 out of 10, Exceptional, (5)
The price is AED 679
AED 1,330 total
includes taxes & fees
8 Jun - 9 Jun
Charming 3-bedroom townhome with AC and WiFi in Waukegan.

Charming Home in Portage Park

10.0 out of 10, Exceptional, (1)
"My family and stayed 2 nights at Alex's place. For us it was a great location equidistant from family events in the city. The 4 bedrooms were all very cozy and comfortable with easy access to bathrooms. The kitchen likewise was super clean and had everything that we needed. As an added bonus the house was only about 200 yards from a great breakfast restaurant call Eggselent. I would not hesitate to book Alex's house again on any return trip to Chicago. "
Charming Home in Portage Park

6 Kings Ping-Pong Gazebo!

10.0 out of 10, Exceptional, (1)
"We had a wonderful stay! The house was extremely clean and well laid out. The kitchen was well stocked. The foosball and ping-pong table in the basement were a hit. We did not use the outdoors but with nicer weather, the outdoors looks like a nice space. The host were extremely responsive to all of our questions prior to the stay. "
6 Kings Ping-Pong Gazebo!

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

9.8 out of 10, Exceptional, (23)
"Perfect location to make training visits to the area. Close to places to eat & grocery stores."
Single Family home in Schaumburg, IL 3 bed/ 2 full baths/ fully fenced backyard

Great 3 bedroom rental unit near Logan Square

9.6 out of 10, Exceptional, (37)
"Safe neighborhood and super responsive host. I would definitely book again."
Great 3 bedroom rental unit near Logan Square

Riverfront Libertyville Retreat w/ Outdoor Kitchen

8.8 out of 10, Excellent, (26)
"Amazing property!! Great location communication with owners throughout our stay. This made our stay with our sailor perfect."
Riverfront Libertyville Retreat w/ Outdoor Kitchen

Master qtr close to nature & easy urban facilities

9.8 out of 10, Exceptional, (54)
"Great trip "
The price is AED 393
AED 706 total
includes taxes & fees
9 Jun - 10 Jun
Master qtr close to nature & easy urban facilities

Urban Farmhouse near O’Hare Airport

9.2 out of 10, Wonderful, (39)
"We enjoyed this old house! It was clean & furnished well. Owner very accessible & easy to work with. Would definitely stay here again!"
Urban Farmhouse near O’Hare Airport

Historic Coach House in Evanston One Block to Beach and Close to Town and NU!

10.0 out of 10, Exceptional, (25)
"I have stayed at this property several times and it is Lovely! The decorating is darling and location is great!"
Historic Coach House in Evanston One Block to Beach and Close to Town and NU!

Family fun-house w/POOL & Game Room, 5 min from Airport and Rosement attractions

8.8 out of 10, Excellent, (6)
"Absolutely Phenomenal!!!!! What a wonderful Christmas staycation for me and my 3 daughter to celebrate together the home we had glean cozy and comfortable living space the basement was our favorite family time spent since my girls are gamers they had fun with the acade game and foosball ,board games enough space to play there other Christmas gifts arctic, the bedrooms omg so comfy and one I stayed in had a beautiful porch access to yard and pool we will definitely be booking to enjoy in...
Family fun-house w/POOL & Game Room, 5 min from Airport and Rosement attractions

Near Lake 4BR w/ Hot Tub & Games | LCP Collection

10.0 out of 10, Exceptional, (10)
"This house had everything we needed and could have wanted! We had a wonderful stay. "
The price is AED 1,146
AED 2,393 total
includes taxes & fees
9 Jun - 10 Jun
Near Lake 4BR w/ Hot Tub & Games | LCP Collection

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

4.0 star property
9.4 out of 10, Exceptional, (40)
"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!!

Your Next Vacation Home

9.8 out of 10, Exceptional, (42)
"The house and the area of town worked out very well for my family. I would stay there again. "
The price is AED 661
AED 1,183 total
includes taxes & fees
17 Jun - 18 Jun
Your Next Vacation Home

Des Plaines Vacation Rental w/ Spacious Backyard!

9.0 out of 10, Wonderful, (8)
"Location was close to family. Property was as described, nice kitchen, laundry, comfortable living room."
Des Plaines Vacation Rental w/ Spacious Backyard!

Breathtaking home close to Schaumburg, Chicago

9.8 out of 10, Exceptional, (56)
"Fit our whole family nicely."
Breathtaking home close to Schaumburg, Chicago

Chic Oasis/Game Room/Near Base/5 Bedroom

2.0 star property
10.0 out of 10, Exceptional, (2)
"Came into town for a bridal shower, house was very clean and very comfortable loving space. Excellent amenities, more than we needed. Kitchen was very well equipped which we appreciated as we did a lot of cooking. Games were definitely utilized!"
Chic Oasis/Game Room/Near Base/5 Bedroom

Cozy 2 bedroom house/w garage in Skokie

10.0 out of 10, Exceptional, (8)
"The house was super nice, the pictures do not do it justice. Great location, nice neighborhood."
Cozy 2 bedroom house/w garage in Skokie

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

10.0 out of 10, Exceptional, (25)
"Nice stay and good location."
100 Yr. Old Chicago Brick Craftsman with yard, Near Beach and Loyola!
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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