Villa vacation rentals in Fairfield County

Find and book unique villas on Airbnb

Top-rated villa rentals in Fairfield County

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

0 of 0 items showing

1 of 3 pages

Villa in Wallkill

5 out of 5 average rating, 3 reviews

Modern Scandinavian Villa

This memorable home is anything but ordinary. You'll be in awe of the soaring ceilings, bright natural light and magnificent chef's kitchen. Nestled in the Hudson Valley just 90 min. from NYC, this remarkable home offers a serene escape for guests. Hidden from the road, this secluded 1920's 3-level stone barn was fully renovated by an award winning NYC architecture firm. On 6 acres, this luxury home's been featured in catalogs, movies and media and offers complete privacy from the outside world.

Top guest favourite

Villa in Newburgh

5 out of 5 average rating, 64 reviews

Ultra Modern Private Oasis with River Views

Step into your brand new, ultra-modern secluded oasis with picturesque views of the Hudson River and Valley. The Balthus Haus was designed and built with sheer comfort, stylish aesthetics, and progressive functionality as the guiding tenets. Nestled high into the hillside the Haus maximizes 360 degrees of privacy and is surrounded by nature. Inviting and pleasant all year round with central AC and radiant heated floors throughout the living areas. Easily get away from NYC only 1.25 hours away!

Guest favourite

Villa in Guilford

5 out of 5 average rating, 31 reviews

TREETOPS! An upscale, unique 5 bdrm home with POOL

TREETOPS is a 4850 square ft 5 bedroom Mid century Modern perched on an outcropping of granite cliffs, surrounded by 2 acres of beautiful forest. *Property not suitable for children under 8 years old* Stroll along the loop trail in our woods, sit in the garden, have a fire in the fire pit, or relax and get some sun by the marine-blue, stone-decked pool! Birdwatching, breakfast, and evening cocktails are best on the spacious wrap-around deck. Hiking is just steps away at "Westwoods Trailhead".

Villa in Hopewell Junction

4.84 out of 5 average rating, 37 reviews

Hudson Valley Haven in Hopewell

Relax at Beekman lodging close to many riches of Hudson Valley, only 60mi from NYC. The hot tub runs all year round and the Heated pool is a delight to win hearts from May thru October. Our 3 bdrm home, sleeping 8 guests, is within 20mi of Dia Beacon to the west, Fishkill Ridge trail to the north, snow sports at Thunder Ridge to the east, and the breathtaking beauty of Wappinger waterfalls to the south. We are also a stone’s throw from multiple farms where apple picking and hayrides abound.

Guest favourite

Villa in Putnam Valley

5 out of 5 average rating, 18 reviews

Bird Haven Farmhouse: Luxury Villa Living w/ Pool.

Escape the city and step into luxury living at Bird Haven Farmhouse, a stylish retreat with all the amenities of a luxury hotel at your fingertips, while in a totally private villa setting. Designer details thru out this 3-Bedroom home: perfect for a summer or winter holiday, while having all the elements needed for a work-from-home set up. The former home of an artist and photographer, Bird Haven's manicured gardens and pool are the perfect setting for your retreat, or as a film location.

Villa in Wingdale

4.87 out of 5 average rating, 15 reviews

Beautiful farmhouse nature escape 90 min from NYC

Relax with the whole family at this peaceful retreat. Feels far more remote than the short drive (or Metro North ride) from the city would suggest! As you make your way down the long tree-lined private driveway and see the classic house and barn, you can feel the atmosphere shift. Come enjoy our spacious farmhouse with antique charm and modern kitchen/amenities. Walk the path around the property, wander the woods, watch the sunrise over the valley, or go apple picking or skiing nearby.

Villa in New Paltz

4.93 out of 5 average rating, 27 reviews

Country home with rock climbing gym, pond & creek.

This country-side home is the perfect retreat whether to work from home or enjoy time off with family and friends surrounded by nature. The home has beautiful creek, pond with Koi fish, local hiking trails only minutes away from the property, and a covered outdoor eating area. Enjoy the homes private rock-climbing gym, outdoor swing, hot tub, fully equipped kitchen, pool table, towel warmers, and good espresso machine. Every room has a dedicated work space with high speed internet.

Villa in Bridgeport

4.79 out of 5 average rating, 14 reviews

Indulge in Prime Luxury 3BR 3-7 Guest

Experience luxury and convenience at our stunning villa! Whether you're planning a group retreat or a family escape, our exquisite property is your ideal haven. Located just moments away from major hospitals, universities, and transportation hubs, our villa provides unmatched accessibility to all your needs. Note: lower level unit listing it might be someone staying/living on the lower unit. They will not be able to disturb or enter the listing separately entrance

Superhost

Villa in East Quogue

4.74 out of 5 average rating, 27 reviews

Farm reserve sunset views

Beautiful villa in beginning part of the Hamptons for a more convenient commute. A private hideaway surrounded by nature where you can relax. It’s perfect for families and friends who love nature, horses and beautiful sunsets. Since our property is spread out over an acre (and surrounded by greater than acre properties), we have the space to allow our guests the ability to maintain a safe distance while still being able to relax comfortably during their stay.

Superhost

Villa in Ossining

4.79 out of 5 average rating, 129 reviews

Castle: Pool, Game Room, BBQ - Pet Friendly

Upstate New York Paradise at Westchester Castle: Your Sunny Group Getaway! 7 Bedrooms, 4 Bathrooms: Sleeps 13 with varied bed types for comfort. Entertainment Galore: Smart TV, pool table, board games. Gourmet Kitchen: Fully equipped for all culinary needs. Relaxation: In-ground pool and indoor tub. Convenience: Free 100 Mbps WiFi, self-check-in/check-out, washer & dryer. Nearby Attractions: Close to parks, family spots, dining, and more!

Superhost

Villa in Guilford

4.91 out of 5 average rating, 11 reviews

Private Luxury Waterfront Home

With uninterrupted and unequaled coastal views, this home is a haven of tranquility. It sits on a special stretch of the Connecticut coast, with spectacular bird and wild life-watching year-round. Enjoy great shopping in Guilford's boutiques around the historic town green. On chilly nights, you can light the fire in the great room and watch the sun set over the water, then hit the hot tub for some star gazing. A slice of pure heaven.

Superhost

Villa in Clintondale

4.33 out of 5 average rating, 12 reviews

Beautiful Modern Villa With POOL SUANA HOT Tub.

SPEND YOUR STAY IN A SPACIOUS AND SUN-FILLED MODERN HOME ACOMMODATING 10 IN COMFORT AND STYLE. Located on a friendly residential road where suburban life fuses with its rural surroundings, this inviting and airy home with its surrounding property offer an experience that will make you wish you lived here full-time. The space SPEND YOUR STAY IN A SPACIOUS AND SUN-FILLED MODERN HOME ACOMMODATING 10 IN COMFORT AND STYLE.