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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
  1. Entire guest suite
  2. Winnetka
Welcome to the North Shore Schoolhouse!

Come find out why many sports celebrities and CEO’s choose to live in Winnetka! Take a weekend or a month at this charming renovated and historic second floor 1 BR apartment just steps from our beautiful Lake Michigan beaches, public transportation, our quaint downtown village and groceries, and our Saturday morning farmers’ market. Walk/run/bike our trails and head for the beach or lagoons!

$142 per night
SUPERHOST
  1. Entire townhouse
  2. Winnetka
Warm and Cheerful 3 Bedroom Winnetka Townhouse

Stay in comfort in the ChicagoLand north shore in a 3 bedroom, 1.5 bath, 2-car garage townhome only blocks from Metra rail, grocery, and restaurants. Upstairs, The master bedroom has a king sized bed, two closets, and a dresser. The 1st guest bedroom has a full bed, a dresser, a single closet and a desk, and the 2nd guest bedroom has a full bed, a dresser and a single closet. On the ground floor the living room/dining room has a sofa, a settee, a few chairs, a 55" TV and a table for four.

$325 per night
  1. Entire rental unit
  2. Northbrook
✨ Guest Room with 1 King Bed + FREE Wifi at Renaissance Chicago North Shore Hotel

Welcome to Renaissance Chicago North Shore Hotel! We offer complimentary shuttle transportation within a 5 miles radius of the hotel! Spacious rooms and suites, curated amenities and an ideal location in Northbrook, IL combine for spectacular results at Renaissance Chicago North Shore Hotel. Ideally situated on the North Shore of Chicago, we offer an optimal location for guests visiting the area.

$135 per night

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Other great vacation rentals in Winnetka

SUPERHOST
  1. Private room
  2. Wilmette
(BR#1) Welcoming, warm & comfortable, 3 guests
$50 per night
SUPERHOST
  1. Private room
  2. Wilmette
(BR#3) Welcoming, warm & comfortable, 1 guest
$35 per night
  1. Entire home
  2. Wilmette
Lovely Wilmette home
$325 per night
  1. Entire home
  2. Wilmette
Elegant house with all comfort & fresh cool vibes
$303 per night
SUPERHOST
  1. Private room
  2. Wilmette
(BR#2) Welcoming, warm & comfortable, 2 guests
$49 per night
  1. Entire home
  2. Winnetka
Chicago Northshore Winnetka 4br
$280 per night
  1. Entire rental unit
  2. Wilmette
2 BR Apartment steps from downtown Wilmette
$200 per night
  1. Entire rental unit
  2. Northbrook
✨ Guest Room with 2 Queen Beds + FREE Wifi at Renaissance Chicago North Shore Hotel
$145 per night
SUPERHOST
  1. Entire rental unit
  2. Wilmette
1 Bedroom Wilmette Apartment steps away from metra
$161 per night
SUPERHOST
  1. Entire home
  2. Glenview
Sweet Glenview Home 4 bd/2 bth, pool & fenced yard
$371 per night
SUPERHOST
  1. Entire rental unit
  2. Wilmette
Downtown Wilmette Micro Studio
$136 per night
SUPERHOST
  1. Entire rental unit
  2. Wilmette
Large Garden Apartment In Historic Wilmette Home
$225 per night
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  5. Winnetka