Holiday rentals with outdoor seating in Callicoon

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.

Location · Value · Amenities

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.

Outdoor spaces · Value · Comfort

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.

Value · Outdoor spaces · Walkability

Secluded Catskills Retreat with Deck and Fire Pit

Welcome to Ridge Haven! Our home features an open floor plan w/ a fireplace, a big deck w/ grill, a seasonal outdoor shower & a fire pit on the upper lawn. Propane & firewood included. Only 2 hours from NYC in the hamlet of Narrowsburg. Nestled against the Delaware River, it is home to a variety of shops, acclaimed restaurants, art galleries, & antique stores. <15 mins from hikes, swimming/tubing on the Delaware, Bethel Woods, and Callicoon. <30-60 mins to skiing (Elk, Big Bear & Shawnee).

Outdoor spaces · Location · Backyard

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.

Outdoor spaces · Value · Heating

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.

Outdoor spaces · Location · Pets

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!

Outdoor spaces · Location · Walkability

Woodsy Retreat, Sunny Home with Paths and Stream

This lovely hand-made home in the woods, lined with windows, flooded with light, has 2 bedrooms and 2 full baths, and a large wraparound deck facing a feisty stream. It has 10 hilly acres of woods with its own paths to wander. Work, relax and play in its inspiring kitchen and lofty spaces stocked with albums, movies, books, art supplies, and instruments. Enveloped in nature, yet only a 10 minute drive to local hot spots including Narrowsburg, Callicoon, Skinners' Falls and Bethel Woods.

Location · Value · Comfort

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.

Location · Outdoor spaces · Air conditioning

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.

Value · Outdoor spaces · TV

Catskills Mountain Chalet l 5 Star experience !

Stylish Chalet in the world famous Catskill mountains privately tucked away on 12 acres surrounded by wildlife and nature. Year-round outdoor activities, fine dining, breweries, and boutique shopping all nearby. Enjoy it all here at Clover Fields! Why "Clover Fields" you ask? Deer visit our property almost daily to graze on our sweet clover fields. It's not uncommon to see them throughout the day. Other notable guests: fox, various birds, woodchucks, chipmunks.

Outdoor spaces · Location · Accuracy

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!

Location · Value · Getting around