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.
Apartment in Park Ridge
4.79 out of 5 average rating, 309 reviewsModern Garden apartment (WHOLE UNIT)
Freshly Remodeled , Lower Level Condo one bedroom one bath. The Condo is very large for a one bedroom. Very Spacious with its open concept layout. Parking is right next to the main entrance of the building. Perfect place to relax Perfect and safe place to rest . 24/7 perimeter monitoring cameras. The Condo is very close to the Metra Train. It is !5 min away from O'Hare airport and 10 min from Chicago outlets etc. It is not a party room . No parties or large gathering .... Garden Apartment
Sep 27 – Oct 4
Home in Wilmette
4.98 out of 5 average rating, 88 reviewsUnique porcelain-enamel paneled "Lustron" home
This rare modern post war home has a style all its own. Created by Carl Strandlund in Columbus Ohio, it consisted of prefabricated porcelain enamel covered panels inside and out making it durable and easy to clean. Easing the postwar housing shortage and its maintenance free design were its selling points. Great care has been taken to reflect its true character so enjoy the well thought out floor plan and huge yard. Close to Northwestern, Gilson park beach, and downtown Chicago via car or train.
Jul 7 – 14
Apartment in Evanston
4.96 out of 5 average rating, 112 reviewsVintage sunlit 2.5 BR apt. Perfect for families!
Welcome to the sunny, spacious, 2nd floor full apartment of our 1920's home! While we live downstairs, the whole upstairs space is yours. Living room, dining room, kitchen w/ DW, full bath, 2 BR, charming sitting room w/ electric FP. Perfect for up to 5 guests. The vintage kitchen is well supplied including Keurig. LR has sofa-bed, love seat, games & 50" ROKU smart TV to connect to streaming services. Kid stuff inc. pk & play Easy 20 min walk for trains to city, 5 min drive to lake. Wifi
Aug 19 – 26
Vacation rentals for every style
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Popular amenities for Winnetka vacation rentals
Other great vacation rentals in Winnetka
Guesthouse in Lake Forest
4.95 out of 5 average rating, 93 reviewsThe Green Door - safe and calm with walkability
Nov 11 – 18
Townhouse in Winnetka
4.96 out of 5 average rating, 26 reviewsWarm and Cheerful 3 Bedroom Winnetka Townhouse
Aug 7 – 14
Apartment in Wilmette
4.82 out of 5 average rating, 17 reviewsThe Shop - Trendy Studio in the heart of Wilmette
Jun 19 – 26
Home in Highland Park
4.98 out of 5 average rating, 49 reviewsCharming Ranch-Style Cottage
Jan 10 – 17
Apartment in Highland Park
5.0 out of 5 average rating, 59 reviewsChic Studio in Downtown Highland Park near Metra
Jul 18 – 25
Home in Skokie
4.89 out of 5 average rating, 64 reviewsLuxe-Haus of Love—The 1938 Cape Cod |Heated FLRS |
Aug 25 – Sep 1
Home in Skokie
4.87 out of 5 average rating, 86 reviewsA+amazing beauty, entire 2 BR Skokie historic stay
Feb 20 – 27
Home in Skokie
5.0 out of 5 average rating, 23 reviewsCulinary DREAM - Pizza Oven/BBQ/Smoker
Jul 24 – 31
Home in Skokie
4.94 out of 5 average rating, 16 reviewsGorgeous 12BD & 5.5BR House w/Ninja Gym - Skokie!
Aug 20 – 27
Condo in Evanston
4.96 out of 5 average rating, 75 reviews"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
May 16 – 23
Apartment in Evanston
4.91 out of 5 average rating, 55 reviewsCozy Neighborhood Escape | Near NU-Chicago-Beaches
Dec 18 – 25
Condo in Skokie
4.93 out of 5 average rating, 15 reviewsFree Parking Balcony, Weekly 5% & Monthly 10% Off
Jul 24 – 31
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