
Cottage holiday rentals in Winnetka
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Top-rated cottage rentals in Winnetka
Guests agree: these cottages are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for cottage rentals in Winnetka
Cottage rentals with a hot tub

The Coral Cottage

The Yellow Cottage @ Cottages on Petite Lake

#4 Adorable Lake Cottage-Cypress Resort & Marine

#8 Hillside Cottage at Cypress Resort & Marine

The Blue Roof Cottage @ Cottages on Petite Lake

The Cozy Cottage @ The Cottages on Petite Lake

The Little Blue Cottage @ The Cottages on Petit

The Lodge @ The Cottages on Petite Lake
Pet-friendly cottage rentals

#2: Cute 2 bedroom cottage on the beach!

Bird House Holiday

Waterfront Fox Lake Vacation Rental w/ Fire Pit!

Driftwood, Cozy Waterfront Cottage, Separate Unit

Klara's Cottage: Yosemite Room

Klara's Cottage: Sunshine Room

Lakefront Cottage w/ Sunset Views
Private cottage rentals

Lakefront Cottage with Gorgeous Sunsets

Charming 1901 cottage blocks away from Bangs Lake.

2BR Skokie Cottage | Walk to Shops | Free Parking

Lakefront Views, Free Water Sports!!

All Season Cozy Cottage

Chic 2BR Cottage | Free Parking, Near Shops/Eats

Key House at Petite Lake Resort, #4
Destinations to explore
- Chicago Holiday rentals
- Indianapolis Holiday rentals
- Downtown Chicago Holiday rentals
- Platteville Holiday rentals
- St. Louis Holiday rentals
- Detroit Holiday rentals
- Louisville Holiday rentals
- Columbus Holiday rentals
- Southern Indiana Holiday rentals
- Cincinnati Holiday rentals
- Milwaukee Holiday rentals
- Wisconsin River Holiday rentals
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- Shedd Aquarium
- Humboldt Park
- Guaranteed Rate Field
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- 875 North Michigan Avenue
- The Field Museum
- Illinois Beach State Park
- Wicker Park
- Brookfield Zoo
- Garfield Park Conservatory
- Museum of Science and Industry
- Lincoln Park Zoo
- Raging Waves Waterpark
- Willis Tower
- The 606
- Racine North Beach
- Grand Geneva Resort & Spa