Holiday rentals in Cook County

Steps from the beach and a mile from National Park

Perfect for family or friends to relax and enjoy Indiana’s Dunes National Park! The Holliday House is a 2022 custom built home with lake views and a beach path just STEPS from the front door! This 2000 sq ft open concept design features 3 bedrooms and 3 bathrooms, 16’ ceilings, open great room with beautiful indoor/outdoor kitchen, custom dining seating for 8, and loft hammock. Hosts live next door and are easily available if needed! Everything is on the 1st floor except for the 3rd bedroom.

Evanston 2BR 2Bth 1 Blk to Beach

With its older charm, modern comforts, and unbeatable proximity to the beach, this 2-bedroom, 2-bath unit offers an ideal getaway. Only 1 block from beautiful Lake Michigan and South Blvd Beach, you will love our spacious, sunny apt. Whether you're staying for a short visit or a lengthy one, you'll feel the comfort of home on a tree-lined street. The unit has hardwood floors throughout, comfortable bedrooms, a fully stocked kitchen, dining room, and a sunroom looking out on the backyard patio.

1920s fully updated unique open artist loft space

True artist living loft space!!! One of a kind space in a safe area of the western suburbs close to the city and easy commute to shops stores. very close to trains buses and expressways. Private parking lot. No unit above or below. Quiet and private spacious updated wide open loft. Hardwood floors throughout forced heat and ac slated steel designer bathroom.. Double oven dishwasher electric cooktop sub zero fridge microwave and toaster oven. Ceiling fans two beds. Can sleep 6 for added cost

Enchanted Garden Treehouse (Amenity*)

Spring is here, the flowers out, the treehouse warm and cozy, and the hot tub ready! Relax on cool evenings in our luxurious, very private, 4' deep cedar hot tub nestled in the evergreens, while the moon and stars swirl overhead, the waterfall cuts thru snow into the koi pond, and the fire table and torches blaze. The running stream makes this a wildlife refuge, with tons of birds, squirrels, rabbits, foxes and hawks. We are 420 friendly. Come experience the magic and make a special memory!

The Ashlin House.

Stay at our family-friendly home on a quiet, cobblestone street on vacation or business. We've recently repainted the exterior and painted the master BR. Walking distance to quaint Downtown Whiting , Lake Michigan, Whihala Beach & Lakefront trails. The Horseshoe Casino, Wolf Lake & Pavilion, Hammond Sportsplex, Calumet College, PNW, IUN, U of Chicago, BP, & golf courses are a short drive. See Chicago's Skyline at Lakefront Park. Chicago's attractions & Hard Rock Casino are < 30 mins away.

Lockports Famous Hideaway ~ 2bdrm Guest House Flat

A history buff’s dream filled with antiques & artifacts relating to Chicago, Joliet, Lockport, the I & M Canal & "Route 66"! Family & Business Friendly. The entire upstairs 1,500 sq ft vintage 2-bedroom house apartment is all your own space. The flat is NOT shared with other guests/host. Private-entrance/self-check-in. Have a 'historic' stay at the "Hideaway"! *Note: Pricing is based on "Double Occupancy". Can accommodate up to 6 guests. Extra charges per person apply after 2 guests.

SW Evanston Private, Stylish, Spacious Suite

Comfort and convenience abound in this stylish suburban suite! Mid-century and vintage motif meets modern touches and style. Guests have the entire basement, with a private bedroom, bathroom, huge living space, and a private entrance in a quiet house on a beautiful treelined street. Backyard access, coffee, easy street parking. Walking distance to parks and public transportation, a short drive to downtown Evanston and the lakefront, easy access to Chicago, Northwestern. Loyola, Skokie.

Elmhurst NEW - Super Clean Modern Farmhouse!

Not your average Air BNB!!! 🏡 Newly renovated - CLEAN modern farmhouse in a great location! ✨ ✅Pet Friendly! 🐕 ✅15 min from O'hare. ✈ ✅25 min to Downtown Chicago 🏦 ✅Close to Grocery, restaurants, coffee, shopping, golf, expressways, down town Elmhurst ,Train and Oakbrook and Fashion Outlet Mall. ✅3 great sized bedrooms, 2 living area sofas converts into sleepers ✅Smart TV in family room and Master. ✅ Back patio with dining and seating ✅Large fenced in yard.

Cozy guest studio, great for couples!

This unique place has a style all its own. Enjoy this beautiful, cozy guest studio with modern touches and well furnished living area, small kitchenette with mini fridge and microwave to reheat a quick bite before heading to the city, full bathroom with rainfall shower and handheld sprayer to help you relax after a long day. Flat screen TV with Xfinity streaming device so you can connect your accounts and enjoy your favorite shows and movies for a quiet stay in.

Cozy French Inspired Cottage in rural setting

Relax and escape to our charming, one of a kind cottage. Beautifully decorated with period furniture and tastefully updated with modern amenities. The cottage offers slate tile and hardwood floors. Original pine floors line the upstairs loft bedrooms. Cook in a French inspired country kitchen with butcher block counter tops. Rural setting, yet minutes away from everything! Downtown is a 20 min. walk and the Metra will take you to the city in 45 minutes!

Cozy three bedroom home in Munster , Indiana.

Plan your next escape to Indiana or Illinois and stay in this beautifully renovated and thoughtfully appointed 3 bedroom and 1 bath home. Located in the quiet and safe suburb of Munster, Indiana, the property is just a 3 minute, easy access to the I-94 Highway. Exciting Downtown Chicago is just 30 minutes away! Walk to Riverside Park and take in the scenic view while enjoying a morning croissant and coffee from one of the quaint neighbourhood cafés.

Cozy Home in Brookfield

Discover tranquility just minutes from the busy city life! Nestled in the heart of Brookfield, IL, our charming home offers the perfect blend of suburban serenity and urban convenience. Just an 8-minute walk from the train station, you'll find easy access to downtown Chicago while enjoying the peaceful atmosphere of our neighborhood. Max 4 overnight guests. No parties or events. Pets allowed (no exotic pets or animals with a bite history).