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.

Superhost

Apartment in Park Ridge

4.79 out of 5 average rating, 309 reviews

Modern 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

$128 per night
Guest favorite

Home in Wilmette

4.98 out of 5 average rating, 88 reviews

Unique 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

$209 per night
Guest favorite

Apartment in Evanston

4.96 out of 5 average rating, 112 reviews

Vintage 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

$126 per night

Popular amenities for Winnetka vacation rentals

Other great vacation rentals in Winnetka

Guest favorite

Guesthouse in Lake Forest

4.95 out of 5 average rating, 93 reviews

The Green Door - safe and calm with walkability

Nov 11 – 18

$85 per night
Guest favorite

Townhouse in Winnetka

4.96 out of 5 average rating, 26 reviews

Warm and Cheerful 3 Bedroom Winnetka Townhouse

Aug 7 – 14

$360 per night
Superhost

Apartment in Wilmette

4.82 out of 5 average rating, 17 reviews

The Shop - Trendy Studio in the heart of Wilmette

Jun 19 – 26

$158 per night
Guest favorite

Home in Highland Park

4.98 out of 5 average rating, 49 reviews

Charming Ranch-Style Cottage

Jan 10 – 17

$137 per night
Superhost

Apartment in Highland Park

5.0 out of 5 average rating, 59 reviews

Chic Studio in Downtown Highland Park near Metra

Jul 18 – 25

$115 per night
Guest favorite

Home in Skokie

4.89 out of 5 average rating, 64 reviews

Luxe-Haus of Love—The 1938 Cape Cod |Heated FLRS |

Aug 25 – Sep 1

$619 per night
Guest favorite

Home in Skokie

4.87 out of 5 average rating, 86 reviews

A+amazing beauty, entire 2 BR Skokie historic stay

Feb 20 – 27

$93 per night
Guest favorite

Home in Skokie

5.0 out of 5 average rating, 23 reviews

Culinary DREAM - Pizza Oven/BBQ/Smoker

Jul 24 – 31

$480 per night
Superhost

Home in Skokie

4.94 out of 5 average rating, 16 reviews

Gorgeous 12BD & 5.5BR House w/Ninja Gym - Skokie!

Aug 20 – 27

$940 per night
Guest favorite

Condo in Evanston

4.96 out of 5 average rating, 75 reviews

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

May 16 – 23

$342 per night
Guest favorite

Apartment in Evanston

4.91 out of 5 average rating, 55 reviews

Cozy Neighborhood Escape | Near NU-Chicago-Beaches

Dec 18 – 25

$139 per night
Guest favorite

Condo in Skokie

4.93 out of 5 average rating, 15 reviews

Free Parking Balcony, Weekly 5% & Monthly 10% Off

Jul 24 – 31

$132 per night

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