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

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

4.88 out of 5 average rating, 125 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, 67 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

4.82 out of 5 average rating, 38 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

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

A spacious two-story home is presented, featuring a mix of stone and white siding. Lush green lawns surround the property, and vibrant trees are visible in the background under a clear blue sky.

Villa in Clintondale

4.37 out of 5 average rating, 19 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.

The spacious home, framed by lush greenery, features large windows reflecting blue skies. A stone wall borders the in-ground saltwater pool, with two lounge chairs positioned nearby. The patio area includes a dining set under a shaded umbrella, creating an inviting outdoor space.

Villa in Garrison

4.95 out of 5 average rating, 98 reviews

Serene and Peaceful - Surrounded by Nature

Tastefully decorated,spacious,open concept,stylish,fine art,luxurious furnishings,4 bedroom,2.5 baths,in Garrison. Stunning views of Hudson Valley. Blue stone patios, in-ground salt water pool, teak furniture. Private,quiet,acreage,verdant landscaping. *Discounts available for extended stays. *Summer/holiday weekend bookings are a minimum of 3 nights.

Top guest favorite

A view of the tranquil outdoor space features a pathway of stepping stones leading to a hand-carved basalt soaking tub, surrounded by lush greenery. The serene water glistens in the background, reflecting the soft hues of the sunrise sky.

Villa in Oyster Bay

5 out of 5 average rating, 6 reviews

The Nest – Design Retreat

Tucked away on Long Island’s Gold Coast in Oyster Bay, The Nest is a one-of-a-kind eco-luxury retreat designed for stillness, connection, and immersive natural living. With bold architecture, a hand-carved basalt hot tub, private yoga deck, and refined interiors, it’s a sanctuary where modern design meets raw coastal beauty.

An airy great room features a striking red accent wall, complemented by wooden beams and large windows allowing natural light to fill the space. A stylish black sofa is positioned near a fireplace, with a collection of plants and bookshelves adding to the decor.

Villa in Newburgh

4.71 out of 5 average rating, 17 reviews

Exquisite Modernism overlooking the Hudson

Beautiful contemporary glass house in Balmville overlooking the Hudson River. Decadently and stylishly appointed with exquisite antiques and mid-century furnishings. An entertainers kitchen, sprawling decks, and panoramic views make this place an entertainers dream, or the perfect retreat just 90 minutes from NYC.