Holiday rentals in Jeffersonville

Cozy A-Frame | Hot Tub, Fire Pit & Pet-Friendly

Escape to the Cedar Haven A-Frame in Damascus, PA – the perfect romantic hideaway just a short drive from NYC. Nestled in peaceful woods, this cozy 400-square-foot retreat offers all you need for a relaxing escape. Soak in the private hot tub, roast marshmallows by the fire pit, or unwind to music as you watch the forest through wide windows. Whether celebrating a special occasion or just needing time away, the tiny cabin invites you to unplug, reconnect, and make memories in nature’s embrace.

The Schoolhouse at Kenoza Lake

The Schoolhouse at Kenoza Lake. This late 1800's renovated schoolhouse is the perfect getaway. Only a 2 hour drive from NYC. Old world charm with modern finishes. House features one bedroom plus a sleeping loft, a total of 3 beds plus a bunk bed, claw foot tub, cast iron wood stove, dinner barn, sleeping loft, vegetable garden, outdoor fire pit with bistro lights and Adirondack chairs. 10-20 min driving distance to all of Sullivan County's culinary offerings. 7 min drive to grocery store.

BirchRidge A-Frame: Sauna/Firepit/King Bed/7 Acres

Nestled in the Catskills Forest, less than 2 hrs from NYC, you'll find Birch Ridge A-frame! This gorgeous 2-bedroom cabin is set on 7 private acres with hiking areas and a seasonal stream. Enjoy the wall of windows that creates a magical stay with breathtaking views. This is the perfect place to relax, sit in the barrel sauna, hike through the private forest, roast marshmallows over the fire, and soak up the sounds of nature. A space that’s made for creating memories that will last a lifetime!

1930's Vintage Cabin · Hot Tub · Kohler Cabin

Escape to Kohler Cabin in Jeffersonville A Rustic Retreat with Modern Comforts Discover the charm of Kohler Cabin, a vintage-inspired retreat nestled in the heart of Jeffersonville. With four bedrooms and two full baths, this cabin offers a unique blend of rustic elegance and modern convenience, perfect for a memorable getaway. Relax and rejuvenate in the screened-in hot tub, enjoy outdoor dining in the fenced-in yard, or simply unwind amidst the tranquil mountain views.

Private, Elegant Chalet w/ A Breathtaking View

Welcome to your all-season escape, to this funky yet luxury, spacious yet cozy, modern yet classic chalet. Where you can experience the perfect vacation, whether it is outdoors with family and friends or appreciating the art pieces throughout the interior. Greet the evenings with a cozy wood-stove and a movie or a glass of wine and a book, sunset with drinks on the deck and the mornings with a fresh espresso. Make some memories at this unique and family-friendly place.

King Of The Hill

Romantic Mountain Top Retreat with Million Dollar Views Escape to this incredibly private, mountaintop vacation home, nestled on 80 acres of pristine land. Offering breathtaking, panoramic views. This peaceful retreat is the perfect getaway for relaxation and romance. Just 2 hours from the GW Bridge, enjoy the tranquility of nature without sacrificing modern comforts, including high-speed internet service. The ideal escape for those seeking both privacy and convenience.

Modern creekside cabin in the Catskills

Welcome to our peaceful little cabin, designed for full immersion in nature. Lounge by the creek with the firepit or hammock, gaze out XL windows, or cozy up by the fire in the living room - every detail invites you to slow down. Tucked on a quiet road just minutes from hiking trails and Willowemoc fly fishing, we’re also only a winding 15-minute drive to charming Livingston Manor, a quintessential Catskills town, and less than 2 hours from NYC.

Bethel Woods Escape: Private Oasis w/ Hot Tub

Welcome to Bethel Woods Escape - a gorgeous modern home surrounded by woodlands of Eastern pine and hemlock trees. In 1969 Bethel Woods was home to the notorious Woodstock festival. Located in the country hills of the Sullivan Catskills, Bethel Woods is an amazing place to explore, hike, and listen to live music. Just 5 minutes away from Bethel Woods Center of the Arts, you will find a stunning A-Frame home waiting to host your next adventure.

Luxury Estate with Wood Stove and Hot Tub

Perched on a hill above the Village of Jeffersonville, Dancing Doe Estate, is a perfect marriage of country charm with the conveniences of small-town life for those looking for a country getaway while not being in an isolated location. The stately blue manor, boasts light-filled spaces, wrap around porch and generous room sizes to very comfortably fit up to 10 guests - 4 bedrooms each with a queen bed and 1 queen sofa bed in the living room.

R52Creekside one bedroom cottage

NEW Construction! Centrally located to all Sullivan county has to offer! Bethel woods, Livingston Manor, Callicoon and much more close by! Walk to a great little local deli and drive to many close restaurants. Set up for two adults or two adults with one small child. Efficiency kitchen (no oven). Ten acres with a creek and lots of area to walk and have a dog. King bed sleeping loft! Great area to explore in summer and winter! Dogs welcome!

The Cabin at Pleasant Valley Farm

The cabin is located on a dirt road on our farm with a beautiful pond and an amazing view! This off-grid, cabin has two queen beds (100% cotton sheets), a mini-kitchen with a battery-ignition gas range, solar powered refrigerator, solar lighting, a wood stove, an outdoor shower, a fire pit, and an old-fashioned outhouse. An expansive porch and dock provide comfortable outdoor living. A seasonal favorite, the cabin is available May-Oct.

Luxe & Modern farmhouse | House of Jane West

Imagine Morticia Addams vacationed in Scandinavia - worked remotely with fast streaming wifi, and then influenced the design of a 1920’s farmhouse in Upstate New York to function both as a remote worker’s dream and an NYC office worker's ideal getaway weekend. In our case, Morticia Addams is known as Jane West, and she was the inspiration for our first weekend home.