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
Guest suite in Chicago
4.98 out of 5 average rating, 111 reviewsGorgeous Studio 15 Minutes From Ohare!
13–20 Sep
$204 NZD per night
Guest favourite
Home in Highland Park
4.9 out of 5 average rating, 125 reviews2-Acre Highland Park Retreat with Heated Pool ~ 5*
21–28 Jan
$2,085 NZD per night
Guest favourite
Loft in West Dundee
4.97 out of 5 average rating, 442 reviewsHip Urban Loft - Small Town Charm- 124 LOFTS #2
28 Oct – 4 Nov
$267 NZD per night
Guest favourite
Guest suite in Wood Dale
4.9 out of 5 average rating, 427 reviewsThe Deer Suite
16–23 Jul
$227 NZD 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
21–28 Mar
$285 NZD per night
Guest favourite
Guest suite in Chicago
4.94 out of 5 average rating, 177 reviewsLincoln Square In-laws Suite: Private Entrance
16–23 Sep
$219 NZD per night
Guest favourite
Apartment in Winthrop Harbor
4.94 out of 5 average rating, 227 reviewsLove my guests! Homey Elegant & Lake Michigan!
27 Sep – 4 Oct
$162 NZD per night
Guest favourite
Apartment in St. Charles
4.98 out of 5 average rating, 226 reviewsQuiet Getaway Near Fox River (Listing 1)
24 Sep – 1 Oct
$210 NZD per night
Destinations to explore
- Downtown Chicago Holiday rentals
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