Ski-in/out vacation rentals in Illinois

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

Top-rated ski-in/out rentals in Illinois

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

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The rooftop pool area is surrounded by lounge chairs and umbrellas, providing space for relaxation. Lush greenery is visible along the perimeter, while the cityscape and nearby buildings create a vibrant backdrop. The pool water is inviting, reflecting the clear sky above.

Apartment in Evergreen Park

Luxurious Condo at lakeshore

Our stunning condo in downtown features: 3 queen beds, 2 master bedrooms with 2 Bath Enjoy modern amenities including a fully equipped kitchen, washer & dyer + Extra Pillows & sheets offers Epic amenities - Co-Working Hubs - Pool & Sundeck with breathtaking views - Parking - Game & Billiards Room - 24/7 Fitness Center - Yoga & Meditation Lounge - Spa & Sauna - Transportation Access - Grilling Area just a 5-minute walk from the iconic Chicago Bean and with a Huge park right under the building.

A modern living area is revealed with large windows showcasing views of the lake and boats. A light-colored sofa and armchair are arranged around a glass coffee table, complemented by a floor lamp and a large TV mounted against a neutral wall.

Condo in Burbank

Iconic Style, Charming Lake View

Enjoy breathtaking views of the lake and boats, with Gorgeous sunrises and sunsets. And Experience the ultimate in luxury and comfort in this exquisite high-rise apartment. This apartment offers the perfect blend of city life and relaxation. This spacious unit features a bedroom with a king-sized bed, a fully equipped kitchen, a large TV, and high-speed WiFi. Premium amenities include an indoor pool available all seasons, spa, hot tub, library, work area with computers, gym, and bar & Much More.

Guest favourite

A serene lakeside view features a dock extending over calm waters, illuminated by a vibrant sunset. The sky displays hues of orange, pink, and purple, with silhouettes of trees in the distance. Two Adirondack chairs offer a comfortable spot for enjoying the landscape.

Home in Fox Lake

4.86 out of 5 average rating, 14 reviews

Sunset Lakefront Cottage in Fox Lake w/ Boat Pier

Come relax at this tranquil lakeside retreat. This spacious ranch-style cottage features a large, west-facing, fenced-in lawn that’s perfect for games and over-the-water sunsets. Three bedrooms make the space comfortable enough for the whole family, or even larger groups. Swim off the dock in a no-wake zone, or take the kayaks or paddleboard out for a paddle around the bay. Come see for yourself what it’s like to live the lake life! Bring Your boat and fishing poles. Enjoy our lakeside firepit.

The spacious bedroom features a king bed with soft bedding, complemented by an accent chair and a lamp. Large windows offer a panoramic view of Chicago’s skyline, allowing natural light to fill the room while city details are visible outside.

Condo in Oak Lawn

Best view and luxury style, Located in Downtown

Experience the best view of your life Chicago's iconic landmarks from this high-rise apartment. Located downtown,you can see Wacker Drive, the lake, Navy Pier, the river,Trump tower from your balcony and room , The place features a spacious bedroom with a king bed , comes fully equipped with essentials, kitchen. large TV, and high WiFi. With premium amenities pool, spa, hot tub, library ,work area,computers,gym, bar. offers the perfect blend of luxury, comfort for a best city life experience

Superhost

An open-concept kitchen and living area features a modern design, highlighted by sleek cabinetry and a spacious island with seating. Natural light fills the room, accentuating the contemporary fixtures and appliances. A comfortable couch is positioned in the inviting living space, creating a perfect gathering spot.

Home in Chicago

4.85 out of 5 average rating, 47 reviews

Executive Contemporary Duplex

Discover a newly remodeled, stylish, & spacious 2-bedroom garden home with a separated basement apartment 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.

A spacious bedroom is illuminated by natural light from large windows showcasing city skyline views. A plush bed with white bedding is complemented by decorative striped pillows. A minimalist nightstand is positioned beside the bed, and a glass door opens to a balcony.

Apartment in Cicero

Scarface Top Richest Lifestyle In Chicago

experience Luxury and Elegance City lifestyle in this Epic Tower and one of the best buildings in the center of Chi Downtown📍 Enjoy Gorgeous skyline views from two rooftop lounges Apartment Features & Amenities: 2 Master bedrooms, 3 Beds, 2 Bath & A Balcony With breathtaking views 1st room 1 King Bed 2nd room 2 Twin beds Fully furnished Fully equipped Kitchen Washer & Dryer WiFi -Parking -Game & Billiards Room -24/7 Gym -Spa & Sauna -Transportation Nearby -Grilling Area -Epic Library

Top guest favourite

A spacious outdoor swimming pool is situated under a covered wooden structure. The pool features a light green surface, surrounded by a wooden deck. Nearby, trees are visible, contributing to the natural setting of the country getaway.

Barn in Carthage

4.94 out of 5 average rating, 71 reviews

Lakefront Barn for Big Group w/swimspa

The Lake Linda Barn is a wonderful secluded country getaway for large groups. You have sleeping for up to 9 people and that's not even putting people on the couches (allowable.) the shared Swimspa is a lot of fun and holds up to 12 people in the middle of the forest. You have access to the host's garden, fresh eggs, and the opportunity to enjoy nature on a beautiful private 44 acre lake and enjoy quiet sunsets or the famous 30 min. "bird walk" around the lake.Clean, simple relaxing space .

Guest favourite

A spacious cement patio offers an expansive view of Lake Shelbyville. The railing frames the scene, while greenery creates a natural border. Comfortable outdoor seating is positioned nearby, inviting relaxation amidst the serene lake and forest surroundings.

Guest suite in Shelbyville

4.9 out of 5 average rating, 60 reviews

Lake Shelbyville Home with a View

Home sits on 62.5 acres next to Lake Shelbyville, one of Illinois largest lakes, overlooking Country Club Cove. Airbnb unit is 40 yards from waters edge with natural walking paths down to the lake. Public boat launches, and 2 parks are 7-10 minutes drive from the property. The north entrance to the Dacey Trail bike and walking paths are 1/4 mile from the property entrance. Horseback riding on the property is allowed with prior approval only.

The bedroom features a spacious bed adorned with an assortment of decorative pillows and a soft throw blanket. Nightstands on either side are accompanied by lamps, providing gentle lighting. A small potted plant adds a touch of greenery to the inviting space.

Home in Galena

4.86 out of 5 average rating, 7 reviews

Lakeview, newly renovated home

Relax with the whole family at this peaceful place to stay. Newly renovated townhouse. 2 bedrooms with a loft, 3 full bathrooms over three floors providing ample space and privacy for all guests. The home has a great lake view, surrounded by all 4 golf courses. Minutes away from Owners Club, fine dining and 15 minutes away from beautiful Downtown Galena. Owners Club with Amenities

A cozy dining area features a dark table and four chairs, situated on a patterned rug against a warm wall. A large TV is mounted nearby, with decorative shelves holding blue and green vases. The kitchen area, adjacent to this space, includes a counter with a sink.

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.

Guest favourite

A light-filled living area features a cozy fireplace surrounded by a stylish brick wall. A comfortable seating arrangement includes two neutral-toned armchairs and a wooden coffee table. Large glass doors open to a private balcony, inviting natural light and offering views of exterior greenery.

Apartment in Lisle

4.8 out of 5 average rating, 5 reviews

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. Ideal for traveling pros near top hospitals. Quiet, nature-filled setting perfect for work and relaxation.

Superhost

A workspace is positioned against a wall, featuring a teal desk and a grey chair. Above, two abstract art pieces add a touch of color. To the right, a shelving unit offers organized storage, complemented by a woven basket. The space has a clean, modern aesthetic.

Private room in Chicago

4.81 out of 5 average rating, 21 reviews

Cozy Private Basement Room | Mini Fridge | TV

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.