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Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

Browse Select Winnetka Cottages

6 Mi to Naval Base: Spacious Waukegan Home w/ Yard
TV, fireplace, books

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

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

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

3.0 star property
Home w/ Fenced Yard: 13 Mi to Downtown Chicago!
Des Plaines Vacation Rental w/ Spacious Backyard!
House (3 Bedrooms) | Private kitchen

Des Plaines Vacation Rental w/ Spacious Backyard!

3.0 star property
Des Plaines Vacation Rental w/ Spacious Backyard!
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Interior

Riverfront Libertyville Retreat w/ Outdoor Kitchen

3.0 star property
Riverfront Libertyville Retreat w/ Outdoor Kitchen
8 Mi to Chicago: Oak Park Home w/ Fenced Backyard!
House (3 Bedrooms) | Interior

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!
Fireplace

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!
Exterior

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!
13 Mi to Dtwn Chicago: Maywood Home w/ Fireplace
House (3 Bedrooms) | Interior

13 Mi to Dtwn Chicago: Maywood Home w/ Fireplace

3.0 star property
13 Mi to Dtwn Chicago: Maywood Home w/ Fireplace
Private Coach house near Lincoln Square!
Interior

Private Coach house near Lincoln Square!

Private Coach house near Lincoln Square!
Lakefront Prospect Heights Home: Ice Fish On-site
Interior

Lakefront Prospect Heights Home: Ice Fish On-site

3.0 star property
Lakefront Prospect Heights Home: Ice Fish On-site
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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Other property types in Winnetka

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (737)
"Great family place to stay. "
The price is CA $187
CA $260 total
includes taxes & fees
May 1 - May 2
Sentral Michigan Avenue
Sonder South Wabash
Superior Apartment, 1 Bedroom, Balcony, City View | Living area

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (484)
"Great stay "
The price is CA $155
CA $182 total
includes taxes & fees
May 26 - May 27
Sonder South Wabash
Sonder Market Hall
Interior

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (277)
"Charming, minimalist, accessible and modern, just what I needed, ideal for couples or single people who want to enjoy the city."
The price is CA $179
CA $210 total
includes taxes & fees
May 26 - May 27
Sonder Market Hall
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.