Holiday rentals in Callicoon Center

Element House - Off Grid Hideout

Unwind and reconnect with nature in this rustic and comfortable retreat nestled at the edge of a blueberry field. Surrounded by serene Catskills countryside, you’ll feel a world away, yet still be just minutes from outdoor activities, a thriving food scene, and Bethel Woods just 35 min away. Inside, you’ll stay cool with AC, a cozy queen bed, kitchenette, dining table, reliable wifi, and full bath. Outside, relax by the fire pit or cook on the charcoal grill. We are an LGBTQ+ inclusive space.

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.

Parkston Schoolhouse

Relax and unwind in this historic converted one-room schoolhouse. Built in 1870, the Parkston Schoolhouse served all grade levels in the Livingston Manor area. The schoolhouse was retired and converted to a cozy cottage style home in the mid 20th century and has recently been renovated into a stylish tiny home getaway. The home is tucked into the hillside along the beautiful, winding Willowemoc Creek and is set amidst a lush Catskill landscape just a five minute drive from Livingston Manor.

Peaceful mountain-top cabin - 5 acres and a gym.

Located 2hrs from NYC, 7mins from Livingston Manor and close to Belleayre and Plattekill ski mountains. Sat atop a mountain, with 5 acres that sweep away from the property revealing stunning long distance views. Beautiful light throughout - front room with fireplace, full renovated kitchen, lounge, dining area, master bedroom, 1 large guest room, office / single bedroom, 2 bathrooms and huge covered back porch + a full home gym complete with Peloton bike, Peloton tread + ping pong table.

Roscoe Cabin Pet Friendly

Book our Pet friendly Cabin A Tranquil Escape in Roscoe, NY Nestled in the woods known as Trout Town USA, our rustic farmhouse cabin with 2 fireplaces offers the perfect retreat for city dwellers seeking relaxation & adventure. Enjoy the scenic 14-mile scenic drive to Bethel Woods Concerts with no traffic. Book your mountain escape with us today and enjoy fresh, clean air, beautiful scenery, and a cozy, well-equipped cabin . We look forward to hosting you & your furry friends soon 🐶

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.

Half Moon: Fairytale Catskills Retreat

Enjoy nature in style at this fairytale in the forest. This idyllic escape combines whimsical structures, curated gathering spaces and a private wooded hillside surrounded by hiking trails and quaint towns. Disclaimer: This is a rustic cabin. Heating is from a wood-burning stove, there is no AC. The bath house is a separate structure from the cabin, up a hillside with stone steps. Cooking is via charcoal grills, small outdoor kitchenette or fire.

Map Maker's Cabin

All season private, cozy cabin in a peaceful woodsy oasis, 15 min from Delaware River; off a main road and close to many peaceful walks. Fast wifi for working remotely, writer's retreat, romantic getaway, meditation, yoga, or time in nature. **We have an (inflatable) hot tub which we fill for guests (unless temps are way too low). NOTE: all-wheel/four wheel drive is highly recommended during winter months. We are looking forward to hosting you!

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.