
Holiday rentals in Highwood
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Top-rated holiday rentals in Highwood
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Holiday rentals for every style
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Popular amenities for Highwood holiday rentals
Other great holiday rentals in Highwood
Top guest favourite

Flat in West Ridge
5 out of 5 average rating, 53 reviewsBrand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
Top guest favourite

Home in Highland Park
5 out of 5 average rating, 16 reviewsNorth Shore - Home Away From Home
Top guest favourite

Home in Northbrook
4.98 out of 5 average rating, 83 reviews*King bed *Outdoor Living *Sought-After Area
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Flat in Highland Park
5 out of 5 average rating, 50 reviewsFull Apartment green oasis in law suite
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Home in Highland Park
4.91 out of 5 average rating, 77 reviewsA Wonderful Getaway Home on the North Shore!
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Home in Highland Park
4.99 out of 5 average rating, 85 reviewsModern & Private Basement Retreat with Kitchenette

Guest suite in Highland Park
4.75 out of 5 average rating, 167 reviewsYour relaxing stay in Highland Park
Top guest favourite

Home in Highland Park
5 out of 5 average rating, 10 reviewsBRAND NEW*Sleeps 7*Near Navy Base*3 BDR*King Bed
Destinations to explore
- Chicago Holiday rentals
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- Traverse City Holiday rentals
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- Shedd Aquarium
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- Alpine Valley Resort
- The Field Museum
- Wicker Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Illinois Beach State Park
- Museum of Science and Industry
- Brookfield Zoo
- Geneva National Resort & Club
- Willis Tower
- Raging Waves Waterpark
- The Beverly Country Club