Holiday houses in Callicoon

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.

Midnight Meadow - Light & Airy Cabin

Midnight Meadow is a bright and airy, recently renovated cabin in the heart of the Catskills, located 2 hours from NYC. Set on 6+ private acres with meadow views, the lodge has 4 bedrooms and 2.5 baths. Amenities include a fireplace, firepit, and access to the best hiking and dining in the region. The lively town of Callicoon is 5 minutes away. If you're looking for accommodations near Seminary Hill, this is just 3 minutes away! This listing has been newly taken over directly by the owners.

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.

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 countryside, you'll feel a world away from it all, yet still be just minutes from outdoor activities, thriving food scene, and Bethel Woods just 35 min away. Inside, you'll find a cozy queen bed, kitchenette, dining table, fast wifi, and a full bath. Outside, relax by the fire pit or cook up a meal on the charcoal grill. We are an LGBTQ+ inclusive space.

Art House Bird Sanctuary at EBC Sculpture Park

The Art House is set in a Sculpture Park being Developed by the artist Tom and Carol Holmes. The Park is 38 acres of rolling hills, grass land with valley views, bordered by two streams and woodlands. The views are magnificent. The house is set on the second tier of three rolling hills 1000 feet up from the road. The property is the newest building project/ABNB offering from Tom; who creates magical and life changing experiences...in the landscape; at EBC Bird Sanctuary Sculpture Park.

Old Schoolhouse in Western Catskills

Our one-bedroom cottage was originally built as a school house in 1849. In 1951 the building was turned into a home, and recently renovated with meticulous care, creating a country retreat with modern amenities. Set on an incline with views over rolling hillsides, the home feels like a treehouse with open views that bring the natural surroundings indoors. 8 minutes from village of Callicoon; 15 minutes to Bethel Woods; 20 minutes to Narrowsburg and Livingston Manor; 2 hours from NYC.

Callicoon Cottage

Romantic Catskills Barn Retreat - Nature's Haven near NYC Welcome to our enchanting barn, Callicoon Cottage, nestled in the heart of the Catskill Mountains, a mere two-hour drive from the bustling energy of New York City. This romantic retreat offers unparalleled privacy and a perfect blend of rustic charm and modern comfort. Whether you're seeking a cozy weekend getaway or a special celebration, our secluded cottage promises an unforgettable experience.

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.

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!