Holiday rentals in Callicoon

The Rustic Barn

This 1865 converted barn is a true sanctuary on 3+ acres w/ woods & fenced yard. Fully renovated interior is bathed in natural light. One bedroom on main level & original loft serves as a second sleeping area. The open plan living room features a wood burning stove, original wide plank floor boards, 25 foot ceiling and views of the private natural landscaping. Near Delaware River, Bethel Woods, boutiques and restaurants. Beautiful private setting, accessible to everything. Under 2 hours to NYC.

Charming Farmhouse on 1/2 acre, w/creek access

Relax in the rocking chairs on the front porch or the hammocks in the large garden. Grill on the deck, roast s'mores over the firepit & stroll or fish along the creek babbling through this quiet hamlet at the foot of the Catskills in the Upper Delaware Scenic Byway. 3 bedrooms, 2 full baths, kitchen, dining room & home office + a spacious yard, leaves room to spread out & relax! 5 min drive to Callicoon shopping/dining/restored 1940s movie theatre 7 min to Simenary Hill 20 min to Bethel Woods

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.

Luxury Historic School House Cottage

Step into history inside our freshly renovated 1800s school house home. Relax and take it easy on the expansive front porch, with sweeping views of rural farmland and a historic cemetery next door. Sit by the fire and enjoy a book or beverage with friends and family and cook a nice farmhouse meal. This unique and tranquil getaway won't disappoint. And it's just 4 minutes from Narrowsburg's Main Street. Swimming holes and hiking trails along the Delaware River are just a stone's throw away.

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.

Modern Catskills Retreat•10 Acres•Hot Tub•Firepit

Welcome to a dream escape, tranquil 3-bedroom modern home that's less than 1-mile off the Delaware River! Built in 2023 and nestled on 10+ acres of pristine countryside delivering peace, quiet and privacy. This exceptional retreat seamlessly combines rustic charm with contemporary luxury, guaranteeing an unforgettable stay. The home features 3 furnished bedrooms sleep up to 7 (3 queen beds, 1 w/ trundle) + a spacious entertainment room flowing directly from the kitchen ideal for hosting.

Chez Cochecton, a modern cabin in the Catskills

Completely renovated inside and out. This unique cabin style home is built for style and comfort. You'll love the thoughtful design and finishing touches. Enjoy some music and wine while relaxing in the private backyard. Cochecton and neighboring towns of Callicoon and Narrowsburg are full of amazing restaurants, shops and hangouts. Situated just off the Delaware River, this home is very close to swimming, hiking, and kayaking. Enjoy all the beautiful Catskills have to offer all year long!

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.

NEW: Streamside by Callicoon: Hot Tub, Sauna & Gym

Hemlock House is the ultimate Western Catskills retreat for large groups. Set on 2.5 private wooded acres in Hankins, you're just 6 minutes from charming Callicoon. Outside, unwind in the hot tub or barrel sauna, gather around the fire pit, play games on the open lawn, and explore a stream with a historic stone bridge. Inside, cozy up by the wood stove, spread out across two living spaces, a screened-in porch, and a game room. Adventure or relaxation — Hemlock House has it all.

Country House on the Callicoon Creek

A very charming, relaxing and inviting space awaits you. The Hortonville House is now available for you. An original 1890's farmhouse sits across from the creek and under a beautiful Sycamore Tree. Fresh air and light provide the perfect setting to enjoy the Delaware River Valley. The home was originally build as the homestead for George Buddenhagen. He took in summer boarders who came to enjoy the Sullivan County. You and loved ones can enjoy the whole home today.

Delaware River retreat

Approximately two hours from the GW bridge - this beautiful country home is located directly on the Delaware River. The house features a full kitchen, a large dining room, and two porches that overlook the river. Watch the eagles, warm up by the fireplace, ski, hike, fish, canoe, swim, eat and laze about. With hi-speed cable and WiFi, tons of space inside and out, this house is perfect for a getaway, staycation, or for families and couples looking to remote-work.