
Villa holiday rentals in Cook County
Find and book unique villas on Airbnb
Top-rated villa rentals in Cook County
Guests agree: These villas are highly rated for location, cleanliness and more.

Luxury Chicago-Wilmette High End Private Residence
Our Property Is Best Described by Our Guests : 5/5 Amazing location and space to breathe We needed a long term place to stay, and wanted a place to LIVE. We needed a home and this was the perfect answer. Located in a beautiful safe neighborhood, literally minutes from the lake, from Old Orchard mall, grocery stores, and everything else we needed. Only a 5 minute drive to a park and ride for the train. Very quiet despite proximity to everything Perfect 10+ We will be back just ! Thank you!

Hot Tub & Sauna: Hoffman Estates Villa in Elgin!
Pets Welcome w/ Fee | 2 Kitchens | Cookout Ready | Quiet 80 Acres This tranquil retreat offers rustic luxury with plenty of space to relax and reconnect. A spacious living and dining area makes it ideal for family gatherings. Set on a peaceful estate, the home features serene views of nature and horses. While it feels secluded, it’s just 36 miles from downtown Chicago, offering easy access to city amenities. You can even watch the Hoffman Estates fireworks from this 6-bedroom, 5-bath home!

Rooftop | Villa | Events
Gorgeous designer space, a mini Villa but large throughout making it light, bright, airy with feelings of calm and tranquility. Party Backyard/Rooftop Indoor features Luminaire Chandeliers, 10 feet ceilings, Grand Piano, Music Box etc. Huge backyard offer spaces to entertain. You’re booking a private residence: Three levels of home exclusive to your guests/party. Guest can view cameras of all entrances; Roof deck, Front, Back & Alley via Monitor (HDMI-1) 24/7 record.

Queen Suite/Terrace in Lakefront Rooftop home
Enjoy a Private terrace view of Chicago life. A minute walk from Tennis court, Golf Course, Beach, Play ground and Cultural Center. A short drive from museums, lake shore, downtown, UofC, restaurants & night life. Enjoy upper home, from your own private patio, to a breathtaking rooftop and relaxing garden. This is 5 ⭐️ w/ Private Bath, Personal fridge/microwave. Massage table, Jacuzzi/spa bath, foot baths, amazing views indoors and outdoors. Enjoy a rooftop party.

Outstanding dune top views of Lake and Nat'l Park
At Villa Santorini, understated elegance sets the stage to behold breathtaking 270-degree views of Lake Michigan, the unspoiled dunes of the Indiana Dunes National Park, and the iconic Chicago skyline. Just 40 minutes from Chicago, it’s the perfect escape to unwind and entertain. Villa Santorini is a spacious blend of unpretentious charm and unparalleled amenities, a comfortable haven for families, friends, or groups looking to unwind and make wonderful memories.

HUGE!3BRPrivateHome+Garage+360°Roof+HotTub+EV+12pp
🎉 3-Story 1,700 sqft Home | Sleeps 12 🎉 ✅DM for YOUR SPECIAL RATE! 🎯 Free Private Garage 🎯 Hot Tub 🎯 360° Roof Deck with Skyline + Willis Tower Views Perfect for family trips, romantic escapes, or friend getaways! ✨ Private keyless entry 🛏 Luxury KING, 2 QUEEN beds + cozy fireplace 🍽 Full kitchen + balcony 📺 3 Smart TVs (Netflix, Disney+, Prime) 🚀 Super-fast WiFi Book now for your unforgettable Chicago stay!

Big Family Fun Paradise | 5 Kings Bed | 16+ Guests
Have fun with the whole family at this stylish place.

Private Room in Equestrian Villa
Relax at this peaceful Equestrian villa.
Popular amenities for Cook County villa rentals
Private villa rentals

HUGE!3BRPrivateHome+Garage+360°Roof+HotTub+EV+12pp

Rooftop | Villa | Events

Hot Tub & Sauna: Hoffman Estates Villa in Elgin!

Luxury Chicago-Wilmette High End Private Residence

Outstanding dune top views of Lake and Nat'l Park

Big Family Fun Paradise | 5 Kings Bed | 16+ Guests
Luxury villa rentals

Outstanding dune top views of Lake and Nat'l Park

Hot Tub & Sauna: Hoffman Estates Villa in Elgin!

Luxury Chicago-Wilmette High End Private Residence

Big Family Fun Paradise | 5 Kings Bed | 16+ Guests
Villa rentals with a hot tub

Outstanding dune top views of Lake and Nat'l Park

HUGE!3BRPrivateHome+Garage+360°Roof+HotTub+EV+12pp

Queen Suite/Terrace in Lakefront Rooftop home

Hot Tub & Sauna: Hoffman Estates Villa in Elgin!
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- 875 North Michigan Avenue
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- The Field Museum
- Wicker Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Brookfield Zoo
- Museum of Science and Industry
- Illinois Beach State Park
- Willis Tower
- Washington Park Zoo
- The Beverly Country Club
- Raging Waves Waterpark
- The 606
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