Villa vacation rentals in Fairfield

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Top-rated villa rentals in Fairfield

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Guest favorite

The three-story building features a modern facade with a mix of dark brick and white panels. Large windows allow natural light to enter the home. A paved driveway leads to a garage door, and neatly arranged landscaping complements the exterior.

Villa in Jersey City

5 out of 5 average rating, 30 reviews

5 Master room with 5 private bathroom close NYcity

This is a brand new construction furnished home which can comfortably accommodate corporate travelers and families. Walking distance to local shops, stores What's Nearby: *12mins to Newport mall-Jersey City, NJ *12mins to Hoboken, NJ *25mins to World Trade Center, NYC *25 mins to Empire State Building, NYC *40 mins bus ride to Manhattan, NJ (Bus station in Time Square) *45 mins to Williamsburg-Brooklyn,NY *14 mins to Newark Airport,NJ *45 mins to Laguardia Airport,NY *55 mins to JFK Airport,NY

Top guest favorite

Villa in Newburgh

5 out of 5 average rating, 74 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!

Superhost

Villa in Guilford

4.89 out of 5 average rating, 36 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".

Guest favorite

A heated salt water pool is surrounded by a stone patio, reflecting sunlight on its clear surface. A Japanese Maple tree provides shade along one edge, enhancing the serene outdoor space. Lush green grass and a white fence enclose the area, creating a private setting.

Villa in Southampton

4.95 out of 5 average rating, 73 reviews

Just renovated Southampton retreat w/ heated pool

JUST RENOVATED! INQUIRE ABOUT MONTHLY RENTALS! Come and enjoy with family and friends your own beautiful house in Southampton. 5-minute drive to Cooper’s Beach and to Southampton Village. Enjoy beautiful ocean beaches, have brunch in the Village, swim in your 32’ heated salt water pool, enjoy a BBQ on your patio under the shadow of a Japanese Maple, indulge in a quiet evening with a book by the fireplace, or take advantage of the home office while your family & friends enjoy the property.

Guest favorite

An aerial view of a spacious property shows a two-story house surrounded by lush greenery and manicured lawns. A gravel driveway leads to the garage, and the outdoor deck is visible on one side, offering a serene environment amidst the trees.

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!

Top guest favorite

Villa in Southampton

5 out of 5 average rating, 102 reviews

Hamptons WaterLiving-Dock, Kayak, Beach, EV charge

[FOLLOW US on INSTA @29watersedge] 1-mile from the beach, this child-friendly waterfront Southampton home is a perfect family getaway. Ready for watersports: kayak, paddleboard, boat, or jet ski. Walk down to the beach for a swim in the bay. At home, the backyard has it all: large dock, fire pit, swing/playset, hammock, grill, & oversized deck to take in the views. Surrounded by nature and water, you are just minutes from restaurants and shopping in Southampton Village &Sag Harbor.

Guest favorite

Villa in Chester

4.98 out of 5 average rating, 42 reviews

Harmony House - A Luxury Retreat Back in Time

Pamper yourself in our beautiful Victorian estate. Built in 1850 and home to one of the most famous racehorses in history, Harmony House is kept in pristine condition & updated w/ modern comforts. Designated a Historic home but running on Solar energy our country-style home offers 7 bedrooms, 4.5 baths, large living spaces & dining areas, chefs kitchen, fireplaces, pool, pool house, patio, grill, lawns & gardens. Walking distance to cafes & shops in Chester & only 50 miles to NYC!

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

Guest favorite

A Mediterranean-style villa is set against a backdrop of lush greenery, featuring a central fountain surrounded by well-maintained landscaping. The two-story structure showcases arched entryways and large windows, reflecting a harmonious blend with the natural surroundings.

Villa in Monroe

4.93 out of 5 average rating, 43 reviews

Mediterranean Villa

Discover the Mediterranean Villa, a stunning 5-bedroom, 4-bath luxury retreat nestled in the scenic Hudson Valley. This Monroe, NY escape offers elegant interiors, a cozy wood-burning fireplace, Smart TVs, a private hot tub, and spacious living areas designed for comfort and style. Perfect for families or groups, it’s minutes from Catskills trails, Woodbury Commons shopping, and acclaimed local wineries. Unwind, explore, and indulge in upscale relaxation year-round.

Guest favorite

The exterior of a modern home is presented amidst lush greenery, featuring a spacious wrap-around deck illuminated by warm lighting. An oversized hot tub is located on the deck, surrounded by natural rock formations and trees, creating a relaxed outdoor setting.

Villa in Tuxedo Park

4.95 out of 5 average rating, 86 reviews

Tuxedo Hilltop Retreat with a Large Hot Tub

Welcome to our peaceful getaway home set in the stunning Sterling Forest Park in the Hudson Valley, only an hour from New York City. Enjoy the tranquil outdoors, the oversized hot tub, the wrap-around balcony, and the spacious deck. Relax in a great room overlooking the forest and unique natural rock formations. And for the ski enthusiasts our home is only 10mi or an easy 20 min drive to Mt. Peter Ski Area.

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, 14 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.

Superhost

A spacious living area is illuminated by natural light, featuring a large, contemporary sofa positioned near a wall-mounted television. A cozy pink pouf is located nearby. A modern fireplace adds subtle warmth, while large windows frame the view of the outside.

Villa in Floral Park

4.75 out of 5 average rating, 4 reviews

The Arena House

Escape to a modern and stylish home just a short drive from New York City. Nestled in a peaceful neighborhood, this upscale villa features a ping pong table, an arcade game, a spacious yard with a basketball court, and all the comforts you need for an unforgettable stay. Perfect for relaxing, recharging, or enjoying time with friends