Ski-in/Ski-out holiday 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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Top guest favourite

Home in Galena

Charming Galena Retreat

Welcome to your peaceful year-round escape in the beautiful Galena Territory. Nestled among towering pines and hardwoods, this home effortlessly blends cozy comfort with outdoor adventure. This home accommodates families seeking a stylish, nature-immersed getaway. Downtown Galena—full of boutique shops, eateries, and historic charm, just a short drive away. Whether you're chasing colorful fall foliage, winter snowscapes, or summer sunsets, this retreat promises memorable stays in every season

FamilyLocationCleanliness

5.0 out of 5 average rating, 11 reviews

Superhost

A spacious deck features comfortable seating arrangements and a small table, perfect for outdoor relaxation. Surrounding greenery offers a natural backdrop, while the home’s charming architecture is complemented by large windows allowing for plenty of natural light.

Home in Spring Grove

The April Inn - A Historic Victorian Lakehouse

Welcome to The April Inn, a charming historic waterfront retreat located directly on Grass Lake in Spring Grove, Illinois, in the heart of the beautiful Chain O’ Lakes. This unique lake house combines the character and charm of a historic Victorian-era home with the outdoor experience that makes a Chain O’ Lakes vacation special. Step outside and enjoy your own private lakefront setting with a pier, lake access, kayaks, expansive yard, deck, outdoor entertaining areas, and beautiful views.

FamilyLocationComfort

4.84 out of 5 average rating, 31 reviews

Top guest favourite

Barn in Carthage

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.

FamilyLocationWalkability

4.96 out of 5 average rating, 89 reviews

Home in Channel Lake

Wooded Nature Retreat Near IL/WI Lakes and Skiing

Your family will be close to everything when you stay at this centrally-located Woodland Retreat Near Wilmot Ski Resort, Fox River Channel Lake, and surrounded by State Park nature area. Escape to your own private slice of nature in this peaceful, tree-surrounded retreat right on the Illinois/Wisconsin border. Whether you're here for skiing, boating, or simply unwinding in the woods, this Antioch getaway puts you close to everything—while still feeling a world away.

HospitalityKitchenCleanliness

Top 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

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.

FamilyLocationCondition

4.92 out of 5 average rating, 72 reviews

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

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

LocationFamilyLayout

4.88 out of 5 average rating, 8 reviews

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

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.

ValueLocationComfort

5.0 out of 5 average rating, 4 reviews

Guest favourite

Home in Fox Lake

3/2 Mineola Bay Lake Retreat with Amazing Views

Welcome to The Prohibition Lakehouse on Mineola Bay - one of the most sought-after spots on the Chain O' Lakes. This newly remodeled 3-bedroom, 2-bath lake house offers breathtaking panoramic water views, unforgettable sunrises, and a true 4-season getaway. Sip your coffee as the lake comes alive with eagles, blue herons, ducks, and even pelicans.

FamilyLocationIndoor spaces

5.0 out of 5 average rating, 7 reviews

A charming lodge-style building with a combination of brick and timber exteriors is framed by lush trees. The scene depicts a serene sky at dusk, enhancing the tranquil ambiance of the resort, with large windows reflecting the twilight hues.

Hotel room in Galena

Club Wyndham Galena IL

You’ll come upon the brick and timber edifice of this resort along a quiet, tree-lined road. The lodge-like design offers peaceful accommodations draped in style and comfort. Second only to Chicago as the most visited destination in Illinois, Galena is a vacation dream.

Flat in Lisle

Panoramic Lake View - Luxury - King Bed - Smart Tv

Designer Deluxe! This completely remodeled 1 bedroom has panoramic views of the lake from your private balcony. Enjoy luxury finishes throughout and laundry-in-unit. Wake up to this stunning lake view with your nice cup of Nespresso! Only 1 parking spot available.

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