Villa holiday rentals in Countryside

Find and book unique villas on Airbnb

Top-rated villa rentals in Countryside

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Superhost

Villa in McHenry

4.9 out of 5 average rating, 29 reviews

Fabulous Cabin

WELCOME TO WATERFRONT LOG-SIDED HOME! ARTISAN CRAFTMANSHIP HOME OFFERS A BACKYARD OASIS SITUATED , NESTLED ON A PRIVATE POND, Heated POOL(closed till April 1st), Hot tub open from Oct 15th to Apr 15thGAZEBO, FIRE PIT, FISHING! 4 BEDROOMS AND 4.5 BATHS The homes sits on the highest point in the neighborhood and has stunning views in the front & backyard! Enjoy the mornings sitting on your front porch. The main floor is completed by an office, finished walkout basement in with a custom built bar

Villa in Elgin

4.25 out of 5 average rating, 8 reviews

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!

Superhost

Villa in South Shore

4.65 out of 5 average rating, 54 reviews

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.

Superhost

Villa in West Town

4.81 out of 5 average rating, 16 reviews

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!

Superhost

Villa in Sheridan

4.17 out of 5 average rating, 12 reviews

Spacious Villa | Various Amenities

Our villa offers an exceptionally spacious escape for you and your group! You'll have access to a number of amazing amenities including 2 pools, a hot tub, a 9-hole mini golf course, basketball, volleyball, and more! In a perfect location for a day trip to Chigaco, while being near natural parks and hiking trails, this is an ideal rental for your vacation.

Superhost

Villa in Sheridan

4 out of 5 average rating, 11 reviews

Villa with Access to Amazing Amenities

When you stay in our villa, you'll have access to a number of amazing amenities including 2 pools, a hot tub, a 9-hole mini golf course, basketball, volleyball, and more! In a perfect location for a day trip to Chigaco while being near natural parks and hiking trails, this is an ideal rental for your vacation.