Villa vacation rentals in Fairfield County

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.

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!

Westchester Autumn BBQ Arcade Event & Pet Friendly

Experience the warmth of fall at The Westchester Manor, a cozy 5-BR, 4-BA estate that sleeps up to 13 guests. Gather by the custom in-house bar, play a round of pool, or enjoy crisp evenings with loved ones after a day exploring Westchester’s autumn colors. With a fully equipped kitchen, Smart TVs, fast WiFi, and pet-friendly comfort, it’s the perfect home for family getaways or group retreats. Make this season memorable with the beauty and comfort of Ossining - Westchester near Sleepy Hollow!

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.

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.

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!

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.

TREETOPS! An upscale, unique 5 bdrm home with POOL

*Please find and book us on the site that begins with a V!* TREETOPS is a 4850 square ft 5 bedroom house perched on an outcropping of granite cliffs, on 2 acres of beautiful forest. *Property not suitable for children under 8 years old* 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".

Cottage in Silvermine: Norwalk New Canaan Wilton

Nestled in a leafy Norwalk neighborhood filled with historic houses, this newly remodeled charming guest cottage/Barndominum on 1 acres in opposite the Silvermine river (where New Canaan, Wilton, and Norwalk meet). The guest cottage is separate from the main house. It is a quaint, quiet and cozy. 1 bedroom 1 bathroom new kitchen including range, dishwasher, Keurig and washer and dryer. The bedroom has a queen bed and the living room has a sofa and chairs. Twin cots can be brought in.

Charming Country Home with Hot Tub, 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, fully equipped kitchen, pool table, towel warmers, and good espresso machine. Every room has a dedicated work space with high speed internet.

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

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.