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Compare 20 Cottages in Winnetka with updated reviews, rates, and availability.

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

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

Family-friendly Villa Park Home: 16 Mi to Chicago!

3.0 star property
10.0 out of 10, Exceptional, (1)
"We recently had the pleasure of staying at this fantastic home with our large family, and I can't recommend it enough! From the moment we arrived, we were greeted by a clean and pleasant neighborhood that immediately put us at ease. The home itself was incredibly roomy, accommodating all of us comfortably. It was spotless and had a warm, welcoming atmosphere that made it feel like a home away from home. We appreciated the thoughtful touches that the owners provided, which added to our overall...
Family-friendly Villa Park Home: 16 Mi to Chicago!

Des Plaines Vacation Rental w/ Spacious Backyard!

3.0 star property
Des Plaines Vacation Rental w/ Spacious Backyard!

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

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

Classic Oak Park Home, 11 Mi to Downtown Chicago!

3.0 star property
Classic Oak Park Home, 11 Mi to Downtown Chicago!

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!

Beautiful+Serene+Upscale EcoGem by ALL the Action~>Beach+Lake+Ravinia+Train+Town

Beautiful+Serene+Upscale EcoGem by ALL the Action~>Beach+Lake+Ravinia+Train+Town

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

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

13 Mi to Dtwn Chicago: Maywood Home w/ Fireplace

3.0 star property
13 Mi to Dtwn Chicago: Maywood Home w/ Fireplace

Riverfront Libertyville Retreat w/ Outdoor Kitchen

3.0 star property
Riverfront Libertyville Retreat w/ Outdoor Kitchen

Lakefront Prospect Heights Home: Ice Fish On-site

3.0 star property
Lakefront Prospect Heights Home: Ice Fish On-site

Charming Illinois Retreat w/ Hot Tub, Deck & Grill

3.0 star property
Charming Illinois Retreat w/ Hot Tub, Deck & Grill

Private Coach house near Lincoln Square!

Private Coach house near Lincoln Square!

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!

3.0 star property
Elegant Mount Prospect Home w/ Fire Pit!

The Winchester - Custom Home w Amazing Outdoors

3.5 star property
The Winchester - Custom Home w Amazing Outdoors

Safe Spacious Mansion Indowntown

4.0 star property
Safe Spacious Mansion Indowntown

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

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

5 Mi to Millennium Park: Apartment w/ Fireplaces

3.0 star property
5 Mi to Millennium Park: Apartment w/ Fireplaces

Prime Location Old Town Chicago Townhome!

3.0 star property
Prime Location Old Town Chicago Townhome!
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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Other property types in Winnetka

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (669)
"Sandra and Joy are welcoming and helpful. Great front desk."
The price is SAR 411
SAR 593 total
includes taxes & fees
2 Feb - 3 Feb
Sentral Michigan Avenue

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (250)
"Enjoyed My Stay."
The price is SAR 424
SAR 497 total
includes taxes & fees
20 Feb - 21 Feb
Sonder Market Hall

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (426)
"Property was convenient and clean. Overall great experience. Street meter parking could be a headache during parking hours but it’s a city thing. Also the incidental feee is a bit confusing with how it’s returned. "
The price is SAR 358
SAR 420 total
includes taxes & fees
25 Feb - 26 Feb
Sonder South Wabash
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.