Ski-in/Ski-out holiday rentals in Illinois

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.

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.

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.

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 .

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.

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, ! Just 20 min to O’Hare, and 20 min Allstate Arena, and 7 min Woodfield Mall

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.

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 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.

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.

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.

The Mulberry Haus

If you're looking for a spacious and cozy rental house in Highland, Illinois for your next get-together, family gathering, or business visits, you've come to the right place. The Mulberry Haus offers a unique combination of comfort and elegance that will make your stay unforgettable.