Villa holiday rentals in Barrington

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Top-rated villa rentals in Barrington

Guests agree: these villas are highly rated for location, cleanliness and more.

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Luxury ChicagoNorthshore HighEnd Private Residence

Chicago's North Shore, one of the most beautiful and sought-after Luxurious neighborhoods The area includes many charming lakefront towns ..walking distance to beaches, scenic parks, boutique shopping, golf courses, and family-friendly attractions while being just a short drive or train ride from downtown Chicago. Whether you're visiting for a relaxing getaway, family vacation, or exploring the city, the North Shore offers the perfect blend of luxury, tranquility, and convenience.

Superhost

A private terrace is accessible through a decorative metal door. The space features wooden flooring and a small bistro-style table with two chairs. A potted plant adds a touch of greenery, while textured walls in the background provide an urban backdrop.

Private room in South Side

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.

Top guest favourite

Villa in Wood Dale

5.0 out of 5 average rating, 60 reviews

Fun 5BR 4.5BA, Pool, Hot Tub, Game Rm, Near O’Hare

Welcome to this spacious and comfortable home in Wood Dale, ideally located near O’Hare Airport and Downtown Chicago. Perfect for families and groups, this home features multiple bedrooms, a fully equipped kitchen, free parking, and relaxing living spaces. Enjoy easy access to shopping, restaurants, parks, and nearby attractions. Whether you're visiting for business or leisure, this home offers comfort, convenience, and great value for your stay.

LocationValueBack garden

Superhost

A grand piano occupies the foreground, showcasing a polished surface that reflects light. Behind it, a spacious area is visible with a row of blue chairs and a ceiling adorned with modern chandeliers, highlighting the open and elegant design of the indoor space.

Villa in South Side

4.67 out of 5 average rating, 57 reviews

Rooftop | Villa

Beautifully renovated luxury residence featuring 3 spacious suites, designer furnishings, antique chandeliers, Young Chang grand piano, new wood flooring, and a spectacular rooftop deck with peek views Lake Michigan views. Family-friendly and ideal for executive or extended stays, the home offers peaceful, elegant living with premium appliances, private terraces, and thoughtfully curated interiors designed for comfort and relaxation.

LocationFamilyLaundry

Superhost

Villa in West Town

4.84 out of 5 average rating, 19 reviews

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

🎉 3-Story 1,700 sqft Home | Sleeps 12 🎉 🎯 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!

LocationFamilyAccess

Guest favourite

Villa in Ringwood

4.9 out of 5 average rating, 223 reviews

Living the High Life Pool House

Relax with family & friends at our large heated indoor pool with a tiki bar, game room & stylish, cozy living space & kitchen. With tons of gathering space, you can enjoy our home in all seasons. *Hot tub added Feb 2nd*

LocationValueParking