Vacation rentals in Winnetka
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Top-rated vacation rentals in Winnetka
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winnetka vacation rentals
Other great vacation rentals in Winnetka
Guest favorite
Guest suite in Chicago
4.98 out of 5 average rating, 111 reviewsGorgeous Studio 15 Minutes From Ohare!
Nov 28 – Dec 5
$70 per night
Guest favorite
Loft in West Dundee
4.97 out of 5 average rating, 442 reviewsHip Urban Loft - Small Town Charm - 124 LOFTS #2
Mar 30 – Apr 6
$119 per night
Guest favorite
Home in Wilmette
4.98 out of 5 average rating, 92 reviewsUnique porcelain-enamel paneled "Lustron" home
Sep 27 – Oct 4
$147 per night
Guest favorite
Guesthouse in Lake Forest
4.95 out of 5 average rating, 96 reviewsThe Green Door - safe and calm with walkability
Mar 7 – 14
$85 per night
Guest favorite
Apartment in Evanston
4.92 out of 5 average rating, 61 reviewsCozy Neighborhood Escape | Near NU-Chicago-Beaches
Jan 6 – 13
$108 per night
Guest favorite
Townhouse in Winnetka
4.96 out of 5 average rating, 26 reviewsWarm and Cheerful 3 Bedroom Winnetka Townhouse
Apr 11 – 18
$332 per night
Superhost
Apartment in Wilmette
4.84 out of 5 average rating, 19 reviewsThe Shop - Trendy Studio in the heart of Wilmette
Jun 19 – 26
$158 per night
Guest favorite
Home in Northbrook
5.0 out of 5 average rating, 15 reviewsNorthbrook Retreat with Ample Outdoor Space
Sep 10 – 17
$274 per night
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