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Browse Select Winnetka Cottages

6 Mi to Naval Base: Spacious Waukegan Home w/ Yard
Relax in this stylish living room with a comfortable sofa, ornate rug, and cozy fireplace.

6 Mi to Naval Base: Spacious Waukegan Home w/ Yard

3.0 star property
10.0 out of 10, Exceptional, (1)
6 Mi to Naval Base: Spacious Waukegan Home w/ Yard
Des Plaines Vacation Rental w/ Spacious Backyard!
Enjoy cooking in this well-lit kitchen with a gas stove, microwave, and stainless steel dishwasher.

Des Plaines Vacation Rental w/ Spacious Backyard!

3.0 star property
Des Plaines Vacation Rental w/ Spacious Backyard!
Home w/ Fenced Yard: 13 Mi to Downtown Chicago!
Fully equipped kitchen with refrigerator, stove, and oven, featuring a clean and organized layout.

Home w/ Fenced Yard: 13 Mi to Downtown Chicago!

3.0 star property
Home w/ Fenced Yard: 13 Mi to Downtown Chicago!
2 Mi to Northwestern: Updated Home w/ Game Room!
Enjoy cooking in this well-equipped kitchen with an oven, range hood, and granite countertop.

2 Mi to Northwestern: Updated Home w/ Game Room!

3.0 star property
10.0 out of 10, Exceptional, (1)
"This recently remodeled home was perfect for our family trip. It was immaculate, comfortable, spacious and well appointed. "
2 Mi to Northwestern: Updated Home w/ Game Room!
8 Mi to Chicago: Oak Park Home w/ Fenced Backyard!
A charming single-story house with a gabled roof and a welcoming entrance.

8 Mi to Chicago: Oak Park Home w/ Fenced Backyard!

3.0 star property
8 Mi to Chicago: Oak Park Home w/ Fenced Backyard!
Oak Park Home w/ Fire Pit - 5 Mi to Garfield Park!
House (3 Bedrooms) | Front of property

Oak Park Home w/ Fire Pit - 5 Mi to Garfield Park!

3.0 star property
10.0 out of 10, Exceptional, (1)
"So cozy. Feels like staying in a guest house with the whole place to yourself! "
Oak Park Home w/ Fire Pit - 5 Mi to Garfield Park!
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Relax in a spacious room with high ceilings, large windows, and a cozy seating area.

Riverfront Libertyville Retreat w/ Outdoor Kitchen

3.0 star property
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Classic Oak Park Home, 11 Mi to Downtown Chicago!
Cozy living room with a leather sofa, ottoman, and dining area, featuring a fireplace and natural light.

Classic Oak Park Home, 11 Mi to Downtown Chicago!

3.0 star property
Classic Oak Park Home, 11 Mi to Downtown Chicago!
13 Mi to Dtwn Chicago: Maywood Home w/ Fireplace
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, and oven, plus a stylish backsplash and wooden cabinets.

13 Mi to Dtwn Chicago: Maywood Home w/ Fireplace

3.0 star property
13 Mi to Dtwn Chicago: Maywood Home w/ Fireplace
Bike & Kayak: Lakefront Prospect Heights Home
House (4 Bedrooms) | Interior

Bike & Kayak: Lakefront Prospect Heights Home

3.0 star property
Bike & Kayak: Lakefront Prospect Heights Home
Private Coach house near Lincoln Square!
A minimalist space with a glass desk, round mirror, and potted plant.

Private Coach house near Lincoln Square!

Private Coach house near Lincoln Square!
Day Trip to Chicago: Hoffman Estates Gem!
Interior

Day Trip to Chicago: Hoffman Estates Gem!

3.0 star property
Day Trip to Chicago: Hoffman Estates Gem!
Elegant Mount Prospect Home w/ Fire Pit!
Interior

Elegant Mount Prospect Home w/ Fire Pit!

3.0 star property
Elegant Mount Prospect Home w/ Fire Pit!
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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Top Winnetka Hotel Reviews

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

10/10 Excellent
"Very walkable to many attractions. Close to many tourist attractions."
William 2-night trip
Posted 19 hours ago
Hilton Garden Inn Chicago Downtown/Magnificent Mile