Holiday rentals 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
Guest suite in Skokie
4.86 out of 5 average rating, 148 reviewsAdorable studio style unit - Self check in ⚡️
14–21 Jul
$207 SGD per night
Guest favourite
Guest suite in Chicago
4.98 out of 5 average rating, 111 reviewsGorgeous Studio 15 Minutes From Ohare!
13–20 Sep
$121 SGD per night
Guest favourite
Guest suite in Wood Dale
4.9 out of 5 average rating, 427 reviewsThe Deer Suite
15–22 Oct
$163 SGD per night
Guest favourite
Flat in Highland Park
4.94 out of 5 average rating, 122 reviewsLovely studio near the beach! (and heated floors!)
24 Nov – 1 Dec
$269 SGD per night
Guest favourite
Home in Lake Bluff
4.92 out of 5 average rating, 102 reviewsHome Sweet Home, minutes to Great Lakes Naval Base
25 Oct – 1 Nov
$193 SGD per night
Guest favourite
Guest suite in Zion
4.89 out of 5 average rating, 138 reviewsNon-smoking, attached mother-in-law suite.
2–9 May
$110 SGD per night
Guest favourite
Guest suite in Chicago
5.0 out of 5 average rating, 293 reviewsPrivate Lincoln Square one bed+bath studio apt.
17–24 Sep
$191 SGD per night
Guest favourite
Guest suite in Chicago
4.94 out of 5 average rating, 177 reviewsLincoln Square In-laws Suite: Private Entrance
15–22 Sep
$140 SGD per night
Destinations to explore
- Downtown Chicago Holiday rentals
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