
Holiday rentals in Winnetka
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Top-rated holiday rentals in Winnetka
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for Winnetka holiday rentals
Other great holiday rentals in Winnetka
Guest favourite

Private room in West Rogers Park
4.95 out of 5 average rating, 193 reviewsWelcoming Evanston Home
Guest favourite

Private room in Highland Park
4.89 out of 5 average rating, 214 reviewsPerfect for Individual Travelers #1
Top guest favourite

Home in Glencoe
5 out of 5 average rating, 5 reviewsCozy 5 bedroom ranch with fireplace & 2 offices!
Top guest favourite

Private room in Evanston
4.98 out of 5 average rating, 181 reviewsPeaceful Suite with natural light. Shared bath
Guest favourite

Private room in Evanston
4.91 out of 5 average rating, 106 reviewsRoom Mins to Downtown Chicago & Northwestern!
Guest favourite

Private room in Glenview
4.89 out of 5 average rating, 384 reviewsGarden Suite with Private Full Bath-Adults Only

Home in Highland Park
New place to stayNorth Shore Chicago Coastal Eco-Retreat
Top guest favourite

Flat in Evanston
4.97 out of 5 average rating, 90 reviewsCozy Apartment Near Shops + Train
Quick stats about holiday rentals in Winnetka
Total rentals
10 properties
Nightly prices starting at
£15 before taxes and fees
Total number of reviews
150 reviews
Wifi availability
10 properties include access to wifi
Popular amenities
Self check-in, Gym and BBQ grill
Local attractions
Tower Road Park/Beach, The Happ Inn Bar & Grill and Spirit Elephant
Destinations to explore
- Downtown Chicago Holiday rentals
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Humboldt Park
- Six Flags Great America
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Brookfield Zoo
- Illinois Beach State Park
- Wicker Park
- The 606
- Raging Waves Waterpark
- Flossmoor Golf Club
- Moraine Hills State Park