Villa holiday rentals in Fairfield County

Group Retreat w. Backyard, BBQ, Gym, Games & More!

Enjoy the best of summer at this spacious family home! The large backyard features a patio with seating, outdoor bar area & BBQ grill. Soak up the sun next to the private pool & jacuzzi (open seasonally). Inside guest can enjoy the full kitchen with double-ovens, dining table for 12, multiple living areas, and tons of natural lighting with tall ceilings & large picture windows. Ideal for group trips, family reunions, or summer escapes this home provides a relaxing setting close to parks & trails

Westchester Summer: Pool Pet Friendly Events Games

Spring and summer escape at The Westchester Manor, a spacious 5BR, 4BA Tudor for up to 13 guests, pet-friendly. Enjoy sunny days by the pool, unwind at the custom in-house bar, and relax with arcade games, pool table, Smart TVs, and fast Wi-Fi. Fully equipped kitchen and in-unit laundry included. Located under 1 hour from MetLife Stadium, East Rutherford, host of the FIFA World Cup 2026. Near Sleepy Hollow, Croton Gorge Waterfalls, and Bear Mountain. Events are welcome, message for more details!

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.

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

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!

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".

Beautiful Colonial Getaway with Private Pool

Come enjoy a country getaway in a rustic home dating to 1768! The colonial charm of this five-bedroom home is sure to capture your heart, offering a beautiful private pool , pool house, barn, and main house with plenty of space for the whole family or a group of friends. Situated on 22 acres of land in rural Connecticut, this home is perfect for a blissful retreat - located only two hours from NYC and three hours from Boston in a picturesque New England town. See notes for pool below.

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.

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.

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.