Holiday rentals in Jeffersonville

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!

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.

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.

Vinyl Pines · Architect Cabin, Hot Tub + Sauna

Architect-designed retreat on 10 private acres — year-round hot tub, sauna, 30ft cathedral ceilings, and a curated vinyl collection, 5 mins from Bethel Woods. Unplug, unwind, and reset your rhythm at Vinyl Pines, a music-inspired getaway down the road from the original '69 Woodstock festival grounds. Set on serene forest with a private walking trail, creeks, and a secluded yoga platform, this upscale sanctuary invites you to spin vinyl by the fire, soak under the stars, and recharge in style.

Chic Cabin on Callicoon Creek

***FEATURED IN ARCHITECTURAL DIGEST, TRAVEL & LEISURE, APARTMENT THERAPY, AND FODORS TRAVEL*** Set back on a small private road, this cabin dating back to the 1800s is perched above the Callicoon Creek, popular with fly fishermen casting for rainbow trout. Head up the wooded driveway and find yourself in a serene, green clearing all your own. The cabin and studio make for a peaceful getaway, shielded from the surroundings, but incredibly convenient for reaching nearby towns and activities.

The Duck Blind at Pleasant Valley Farm

This tiny one-room cabin is located on Pleasant Valley Farm with its own large 4-acre fishing pond. Originally built as a duck blind, the 10 x 15 ft. off-grid camp cabin can easily accommodate two adults with a trundle daybed that doubles as a couch. An expansive covered porch, dock, gravel patio with picnic table, and an awesome stone firepit provide added outdoor living space. Tucked into a grove of trees, this is a very private place to relax, unwind, and go fishing or kayaking.

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.

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.

Bethel Woods Escape: Private Oasis

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.

Catskill Retreat

Slow down and relax in this split-level cottage in the woods. With a waterfall crossing underneath the deck, the cottage features stone floors, living room with stone fireplace, large bedroom and loft, and a well-equipped kitchen to prepare dinner on the screened porch. Just a mile away from a supermarket, restaurants, a bakery, and a weekly seasonal farmer's market.

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.