Villa vacation rentals in Fairfield

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Top-rated villa rentals in Fairfield

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An aerial view reveals a bright dining area with large glass doors allowing natural light to fill the space. A wooden table is surrounded by modern white chairs, while a cozy chair and textured rug add warmth to the minimalist decor.

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.

Superhost

The outdoor area features a spacious in-ground pool illuminated by the twilight sky, surrounded by a stone patio. Comfortable lounge chairs line the edge of the pool, with the inviting exterior of the home visible in the background, showcasing multiple windows reflecting warm interior lighting.

Villa in Cornwall

4.85 out of 5 average rating, 94 reviews

Jacuzzi - West Point - Family Friendly

Knoll Shoal: Your Ultimate West Point Getaway A perfect blend of autumn’s cozy charm and the beauty of winter: 7 Bedrooms, 6 Bathrooms: Sleeps 16+ with 9 beds. Entertainment: Smart TV, BBQ, Games, Fire pit. Gourmet Kitchen: Fully equipped for all culinary needs. Relaxation: In-ground pool, Jacuzzi, and multiple fireplaces. Convenience: Free fast Wi-Fi, washer & dryer, dedicated workspace. Within Cornwall-On-Hudson, West Point, New Windsor, New Burgh, Beacon, Mountainville, Highland Falls.

Superhost

A spacious lawn is bordered by trees, displaying an array of green shades under a clear blue sky. A stone-edged pool is visible in the foreground, adding a tranquil element to the expansive outdoor landscape.

Villa in Morris

4.89 out of 5 average rating, 131 reviews

LuxeCompound-HotTub Pool Sauna Treehouse Gamebarn

Serene, elegantly appointed 19th century compound, fully modernized and set on the edge of a 50 acre land preserve next to boat friendly Bantam Lake. Located in the rolling hills of Litchfield County this expansive home has four buildings and every amenity: pool, hot tub, heated gym, cedar sauna, central AC, 2 chef’s kitchens, game barn, primary suite with wb fireplace and soaking tub, a pool house guest suite with steam shower, & treehouse w/ slides & a swing set built on a 300yr old oak tree.

Top guest favorite

A contemporary living room features an 18-foot tall cathedral ceiling and a mix of stylish furnishings. Two couches are positioned around a circular blue rug, while a serene hammock hangs from the ceiling. A fireplace serves as the focal point, with plants adding life to the space.

Villa in Newburgh

5 out of 5 average rating, 70 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 favorite

The exterior of the house is framed by lush greenery, with a wrap-around deck highlighted by large windows. The warm glow from the interior lights contrasts with the natural surroundings, while the fieldstone chimney adds an element of rustic charm. A pathway leads towards the entrance.

Villa in Guilford

5 out of 5 average rating, 34 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".

An outdoor heated pool surrounded by a brick patio is framed by a wooden fence and lush greenery. Two lounge chairs are positioned nearby under a large umbrella, providing a relaxing space for sunbathing. The serene setting invites enjoyment of the fresh air.

Villa in Hopewell Junction

4.8 out of 5 average rating, 40 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 favorite

An aerial view of the property reveals a spacious lawn surrounded by manicured gardens and trees. The charming farmhouse is visible along with a patio area, swimming pool, and additional buildings, set against a backdrop of vibrant greenery under a clear blue sky.

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.

Guest favorite

The exterior of a spacious, two-story house is captured at dusk, with warm lights glowing from the windows. The surrounding lawn is expansive and well-maintained, featuring soft outdoor lighting along the pathway, enhancing the serene ambiance of the property.

Villa in Wallkill

4.98 out of 5 average rating, 45 reviews

Spiti Helios: luxury retreat w/hot tub & pool

Καλώς Ορίσατε (welcome) to the beautiful Hudson Valley surrounded by distilleries, wineries (Magnanini Winery 6 minutes away 😉), spas, nature, and whatever your heart desires. Come zen out in this luxurious gem nestled on nearly 2 acres of privacy~did we mention the hot tub? *2-3 night stays get a discounted rate *Please enter all daytime visitors and overnight guests at time of inquiry. For early / late check out options check “other details”. Now let’s kick back and enjoy the Gunks!

Guest favorite

A tranquil winter scene depicts a classic farmhouse and a red barn surrounded by a blanket of fresh snow. A path is visible in the snow, leading toward the inviting buildings, and tall trees are present in the background, adding to the serene atmosphere.

Villa in Wingdale

4.88 out of 5 average rating, 16 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.

An inviting living area features a stone fireplace accompanied by a large flat-screen TV. Colorful artwork and decorative accents include modern furniture and plush seating. Large windows allow natural light to fill the space, while a dining area is visible in the background.

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

Expansive green lawn extends towards the horizon, bordered by white fencing and mature trees. A serene landscape is visible with grazing horses in the background. Bright blue sky complements the lush surroundings, creating a peaceful outdoor environment.

Villa in East Quogue

4.74 out of 5 average rating, 31 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.

Top guest favorite

A spacious bedroom features a king size bed against a wall with large windows offering pleasant views. Two green chairs are positioned around a small table, creating a cozy seating area. Light wood accents on the ceiling enhance the room's airy feel.

Villa in New Paltz

5 out of 5 average rating, 13 reviews

Country House, Mountain Views, Dine, Bike, & Hike

Welcome to Enthusiastic Spirits Main House. World class climbing, biking, swimming, and endless exploring. The Hudson Valley is dotted with great restaurants, craft wineries and distilleries, art galleries, local crafts and historic attractions. New Paltz, Mohonk and Minnewaska are just 10 min away. Simply, a great place to stay and play. We no longer have a hot tub available on this property.