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Vacation 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.

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!

  1. Private room
  2. Wilmette
Cozy, one-bedroom retreat

Comfy private small bedroom and bath (we have our own master bathroom but we do share the shower occasionally) in an artist's home with European feel. Access to the kitchen and backyard. Near cafes, beach, and roads and trains that whisk you to the Windy City. Anastasia is a multi-lingual host and composer, author, artist.

  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.

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Other great holiday rentals in Winnetka

SUPERHOST
  1. Private room
  2. Wilmette
(BR#3) Welcoming, warm & comfortable, 1 guest
  1. Entire home
  2. Wilmette
Unique porcelain-enamel steel panel "Lustron" home
  1. Entire home
  2. Winnetka
Chicago Northshore Winnetka 4br
  1. Entire rental unit
  2. Northbrook
✨ Guest Room with 1 King Bed + FREE Wifi at Renaissance Chicago North Shore Hotel
  1. Entire rental unit
  2. Wilmette
2 BR Apartment steps from downtown Wilmette
SUPERHOST
  1. Entire rental unit
  2. Wilmette
1 Bedroom Wilmette Apartment steps away from metra
SUPERHOST
  1. Private room
  2. Wilmette
(BR#2) Welcoming, warm & comfortable, 2 guests
SUPERHOST
  1. Entire home
  2. Wilmette
Wilmette "Treetops" Getaway
SUPERHOST
  1. Entire home
  2. Glenview
Sweet Glenview Home 4 bd/2 bth, pool & fenced yard
SUPERHOST
  1. Entire rental unit
  2. Wilmette
Large Garden Apartment In Historic Wilmette Home
SUPERHOST
  1. Entire rental unit
  2. Wilmette
Downtown Wilmette Micro Studio
  1. Entire guesthouse
  2. Glenview
Secluded guest house/inlaw apartment with parking