Ski-in/Ski-out holiday rentals in Cook County

Find and book unique ski-in/out homes on Airbnb

Top-rated ski-in/out rentals in Cook County

Guests agree: these ski-in/out homes are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 2 pages

Superhost

Home in Chicago

4.88 out of 5 average rating, 25 reviews

Executive Contemporary Duplex

Discover a newly remodeled, stylish, & spacious 2-bedroom garden home nestled in the historic Bronzeville neighborhood. This beautiful residence boasts enchanting décor and well-appointed living spaces that promise a memorable stay. Its minimalist charm and comfortable setup reflect a contemporary/modern aesthetic, making it an irresistible choice for guest. Just 6 mints from the downtown, 20 mints from Midway Airport, and 4 mints from McCormick Place & UOC, it's perfect for any length of stay.

Flat in Chicago

4.81 out of 5 average rating, 26 reviews

3BR Luxury Modern Apartment

This is the place to be in downtown Chicago! This new building offers you comfort and luxury in one of the most desirable locations. Flooded with natural sunlight the spacious living room, fully equipped kitchen and bedrooms open up to a stunning mesmerizing view. The modern apartment building offers a sun-filled outdoor pool, a fitness center and beautiful appointed outdoor courtyard. Enjoy those summer days in your luxury apartment or the amenities outside.

Home in Rolling Meadows

4.57 out of 5 average rating, 28 reviews

Modern townhouse in Rolling Meadows

Welcome to this Modern Casa Exelente location, Rolling Meadows on. Bring your family, guests can check in without time restrictions, ! This clean and safe space is clean and safe, …1 first floor of this house all complete and private, It has 3 bedrooms, living room, kitchen, dining room, bathroom, terrace, ! luxury kitchen! The images say more than a thousand words, ! A solo 20 minutos al O’Hare, y 20 min Allstate Arena, y 7 minutos Woodfield Mall

Flat in Lisle

New place to stay

2BR w/Balcony, Fireplace & Wi-Fi

Stylish 2BR in serene Four Lakes community. Fully furnished with all utilities, Wi-Fi, and 2 rare front-row parking spots included. Enjoy a cozy fireplace, private balcony with tree views, and peaceful resort-style amenities—pool, gym, ski hill, and more. Ideal for traveling pros near top hospitals. Quiet, nature-filled setting perfect for work and relaxation.

Superhost

Private room in Bolingbrook

5 out of 5 average rating, 4 reviews

A place to quietly enjoy nature

Bring the whole family to this great place with lots of room for fun. If you love nature, walking in the woods by the river this is the place to be. We are within walking distance of great restaurants movie theaters etc... Arrangements can be made with host for pick up/ drop off at the airport or anywhere else, and any other type transportation services.

Private room in Chicago

4.6 out of 5 average rating, 10 reviews

Cozy Private Basement Room | Mini Fridge | Desk

This is the basement room in a duplex down first floor apartment in Albany park neighborhood of Chicago. Upstairs has shared bathroom & shower, common areas like kitchen and living room. Laundry is next to the bedroom in the basement as well. Free wifi, kitchen is full with appliances. Gas and electric included.