Highwood Vacation Rentals
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Vacation Rentals in Highwood
AeroStay Retreat – 4BR Home Near O’Hare Airport!
Wood Dale IL
Located in Wood Dale, this vacation home is within a 15-minute drive of Donald E. Stephens Convention Center and Allstate Arena.
Kitchen
Washer
Your Next Vacation Home
Des Plaines IL
$282 nightly
The price is $302 total per night
$302 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
With a stay at this vacation home in Des Plaines (Oakton), you'll be a 3-minute drive from Allstate Arena and 7 minutes from Donald E. Stephens Convention Center.
Kitchen
Washer
Family frndly TwnHm by navy base
Waukegan IL
With a stay at this vacation home in Waukegan, you'll be a 2-minute drive from Lake Michigan and 7 minutes from Naval Base Great Lakes.
Kitchen
Washer
Urban Farmhouse near O’Hare Airport
Des Plaines IL
When you stay at this vacation home in Des Plaines, you'll be on a river, within a 10-minute drive of Allstate Arena and Donald E. Stephens Convention Center.
Kitchen
Washer
Beautiful Updated Home near Great Lakes Naval Base
Waukegan IL
With a stay at this vacation home in Waukegan, you'll be a 3-minute drive from Lake Michigan and 8 minutes from Naval Base Great Lakes.
Kitchen
Washer
Breathtaking home close to Schaumburg, Chicago
Palatine IL
With a stay at this vacation home in Schaumburg, you'll be within a 5-minute drive of Schaumburg Convention Center and Woodfield Mall.
Hot Tub
Kitchen
Charming 3-bedroom house in Grayslake
Grayslake IL
With a stay at this vacation home in Grayslake (Gages Lake), you'll be within a 15-minute drive of Naval Base Great Lakes and Gurnee Mills.
Hot Tub
Kitchen
Quaint Bungalow, near Great Lakes Naval Base
Mundelein IL
$313 nightly
The price is $332 total per night
$332 total
Dec 15 - Dec 16
Total with taxes and fees
With a stay at this vacation home in Mundelein, you'll be within a 15-minute drive of Naval Base Great Lakes and Pine Meadow Golf Club.
Kitchen
Washer
Spacious New 5 Bed Family Retreat Near Naval Base!
Waukegan IL
With a stay at this vacation home in Waukegan, you'll be a 5-minute drive from Lake Michigan and 9 minutes from Naval Base Great Lakes.
Kitchen
Washer
Cozy Home near O'Hare & fun Hubs with AC
Des Plaines IL
With a stay at this vacation home in Des Plaines, you'll be within a 5-minute drive of Allstate Arena and Donald E. Stephens Convention Center.
Value Stay: Home - 2 Bedrooms
Waukegan IL
$228 nightly
The price is $242 total per night
$242 total
Dec 14 - Dec 15
Total with taxes and fees
With a stay at this vacation home in Waukegan, you'll be within a 10-minute drive of Naval Base Great Lakes and Six Flags Great America.
Washer
Dryer
Master qtr close to nature & easy urban facilities
Riverwoods IL
$176 nightly
The price is $187 total per night
$187 total
Dec 25 - Dec 26
Total with taxes and fees
With a stay at this vacation home in Deerfield (Riverwoods), you'll be within a 15-minute drive of Lake Michigan and Ravinia Green Country Club.
Hot Tub
Free WiFi
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.
Highwood Vacation Rentals essential information
Accommodation | 342 Vacation Rentals |
|---|---|
Lowest Price | $187 |
Highest Price | $332 |
Popular accommodation | AeroStay Retreat – 4BR Home Near O’Hare Airport!, Your Next Vacation Home, Family frndly TwnHm by navy base , Urban Farmhouse near O’Hare Airport, Beautiful Updated Home near Great Lakes Naval Base, Breathtaking home close to Schaumburg, Chicago, Charming 3-bedroom house in Grayslake, Quaint Bungalow, near Great Lakes Naval Base, Spacious New 5 Bed Family Retreat Near Naval Base!, Cozy Home near O'Hare & fun Hubs with AC, Value Stay: Home - 2 Bedrooms , Master qtr close to nature & easy urban facilities |