Holiday houses in Winnetka
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Top-rated holiday rentals in Winnetka
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Winnetka holiday rentals
Other great holiday rentals in Winnetka
Guest favourite
Apartment in Wilmette
4.89 out of 5 average rating, 235 reviewsSpacious Garden Apartment with Sauna and Fireplace
28 June – 5 July
$3,019 AUD total
Guest favourite
Guest suite in Chicago
4.98 out of 5 average rating, 111 reviewsGorgeous Studio 15 Minutes From Ohare!
29 Oct – 5 Nov
$1,311 AUD total
Guest favourite
Loft in West Dundee
4.97 out of 5 average rating, 442 reviewsHip Urban Loft - Small Town Charm - 124 LOFTS #2
2 – 9 Feb
$1,710 AUD total
Guest favourite
Home in Wilmette
4.98 out of 5 average rating, 92 reviewsUnique porcelain-enamel paneled "Lustron" home
27 Sept – 4 Oct
$1,984 AUD total
Guest favourite
Guesthouse in Lake Forest
4.95 out of 5 average rating, 96 reviewsThe Green Door - safe and calm with walkability
4 – 11 Oct
$1,252 AUD total
Guest favourite
Apartment in Evanston
4.92 out of 5 average rating, 62 reviewsCozy Neighborhood Escape | Near NU-Chicago-Beaches
6 – 13 Jan
$1,671 AUD total
Guest favourite
Townhouse in Winnetka
4.96 out of 5 average rating, 26 reviewsWarm and Cheerful 3 Bedroom Winnetka Townhouse
4 – 11 Apr
$4,351 AUD total
Superhost
Apartment in Highland Park
5.0 out of 5 average rating, 40 reviewsStunning & Stylish Downtown Studio - Highland Park
20 – 27 Sept
$1,608 AUD total
Destinations to explore
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