Villa holiday rentals in Fairfield County

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Top-rated villa rentals in Fairfield County

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Villa in Monroe

4.73 out of 5 average rating, 80 reviews

Awesome Country Retreat - 4BR - Private & Peaceful

Just an hour from downtown NYC, my spacious country home offers the perfect retreat for families or friends. Whether you're soaking in the jacuzzi-style bath, roasting marshmallows by the fire pit, or enjoying the warm grass beneath your feet, this property is designed for ultimate relaxation with loved ones. Secluded and private, yet only a 5-minute drive to the charming town of Monroe, this home offers both tranquility and convenience. Professionally cleaned and managed for your peace of mind

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, 30 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 favourite

Villa in Deer Park

4.86 out of 5 average rating, 77 reviews

A Modern Getaway Perfect for Families & Business

Discover the perfect blend of style and functionality in this modern two-story home, ideal for both family retreats and business gatherings. It boasts 4 bedrooms, 3 bathrooms, 2 fully-equipped kitchens, and 3 spacious living rooms. With 6 comfortable beds, an authentic wood-burning fireplace, and 4 smart TVs, you’ll find all the comforts of home. Enjoy the private balcony, 2 outdoor furnished patios, BBQ grill for entertaining, 3 bicycles and 6 private parking spots for you and your guests.

Guest favourite

Villa in Wallkill

4.98 out of 5 average rating, 42 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!

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.

Guest favourite

Villa in Hampton Bays

4.94 out of 5 average rating, 18 reviews

Picturesque 5-bedroom Hamptons villa with pool

Relax with the whole family at this peaceful place to stay. Go for a swim in the 20’ x 40’ heated pool or enjoy the scenic garden and woods while lounging in the outdoor living room. Grill some burgers or make s’mores over the fire pit. Centrally located. 6 min. drive to LIRR and Hampton Jitney and minutes to I-495. 2 mins. to bay beaches and 10 mins. to ocean beaches. 10 mins. to Southampton Village. 20 mins. to the wineries. Explore all the Hamptons have to offer and more!

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, 128 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.