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Compare 647 Vacation Homes in Winnetka with updated reviews, rates, and availability.

Great 3 bedroom rental unit near Logan Square
Great 3 bedroom rental unit near Logan Square
9.4 out of 10, Exceptional, (30)

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
10.0 out of 10, Exceptional, (164)

Cozy 3-bedroom house in family-oriented Melrose Park.
Cozy 3-bedroom house in family-oriented Melrose Park.
10.0 out of 10, Exceptional, (9)

Updated Forest Park 3 BR Bungalow
Updated Forest Park 3 BR Bungalow
10.0 out of 10, Exceptional, (101)

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
9.2 out of 10, Wonderful, (90)

Charming ModernRetro Home!
Charming ModernRetro Home!
9.2 out of 10, Wonderful, (14)

Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover
Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover
9.4 out of 10, Exceptional, (12)

2 King Bdrms and 1 Queen Bdrm! 20 minutes to O'Hare Airport! Parks and Shopping!
2 King Bdrms and 1 Queen Bdrm! 20 minutes to O'Hare Airport! Parks and Shopping!
9.4 out of 10, Exceptional, (18)
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
Sentral Michigan Avenue
9.2 out of 10, Wonderful, (736)
The price is AED 496
AED 691 total
includes taxes & fees
30 Apr - 1 May

Sonder South Wabash
Sonder South Wabash
9.0 out of 10, Wonderful, (482)
The price is AED 453
AED 532 total
includes taxes & fees
26 May - 27 May

Sonder Market Hall
Sonder Market Hall
8.6 out of 10, Excellent, (274)
The price is AED 485
AED 570 total
includes taxes & fees
26 May - 27 May
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.
Recent reviews of Winnetka hotels
Recent reviews of Winnetka hotels

River Hotel
5/5 Excellent
"Fabulous location in downtown. Staff is so courteous and nice it was a pleasure. Incredible view to the river. Very comfortable bed and linens and the best pillows I had in a long time. Loved the free filtered water. Definitely will be back."
A verified traveler from Boulder stayed at River Hotel
Posted 13 hours ago