Villa holiday rentals in Fairfield County

Westchester Winter - Fireplace Events Pet Friendly

Winter retreat at The Westchester Manor, cozy 5BR, 4BA villa for 13 guests in Ossining. Unwind by the in-house bar, pool table, relax with Smart TVs and fast WiFi. Fully equipped kitchen and pet-friendly. Nearby winter highlights include Sleeply Hollow, Rockefeller State Park Preserve snowy trails, Croton Gorge Park frozen waterfalls, Hudson RiverWalk views, Tarrytown holiday lights and Bear Mountain WinterFest. Perfect for family or group stays. Events welcome, contact us in Airbnb for 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.

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!

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.

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.

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.

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

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.

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.