Holiday houses in Handsome Hollow

The Waterfall Casita: A-frame with 30ft Waterfall

Nestled among Hemlock trees & steps from a 30 ft waterfall is our cozy A-frame cabin. Sitting on 33 private acres connected to state land, enjoy waterfall views while sipping coffee in front of the fireplace. The casita was intentionally designed to feel like a home away from home. In summer, cool off in the waterfalls & private streams, in autumn take in the stunning foliage & in winter ski/snowboard at Belleayre (25 mins away). Alder Lake & the Pepacton Reservoir fishing are a 10 min drive.

Value · Location · Nearby

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 · Family · River

Tiny House Cabin On The Delaware

This 2 bed 1 bath cabin is steps from the river with beautiful mountain views. The home has 1 bedroom with a queen size bed and a loft with a queen size bed. 3 new flat screens, washer and dryer, and all the amenities you could need. New appliances in the kitchen and new pots, pans, and utensils for cooking, as well as fully stocked linen, extra bedding, and towels. Please be aware that the cabin is located right by a Route 17 overpass but, the cabin is beautiful, relaxing and quieter inside.

Family · Location · Pets

Close to Cute Towns~Labor Day~Firepit

Stylishly designed mid-century cottage surrounded by nature • Livingston Manor 12 min, Bethel Woods Center for the Arts 17 min. • Great for couples or small families • Walnut Mt. hiking 8 min. • Gas grill & fire pit • Rocking chair front porch • 2 queen bedrooms, open living area, 1 bathroom. • Fully-stocked kitchen/beautiful cabinets and open shelves. • Relax inside or explore the backyard's natural beauty. • Indulge in the luxury of a clawfoot tub. You'll love it! Book with us now!

Family · Location · Parking

The Mill House: An Enchanting Stream-Side Retreat

Nestled in the heart of the Catskills and just a 2.5-hour drive from NYC, escape to the perfect fall retreat where you can reconnect with nature and enjoy the serene beauty of the season. This historic gem underwent a recent restoration, marrying its saw mill heritage with contemporary luxuries, including a Nest thermostat, smart speakers, keyless entry, and fast wifi. Original exposed post and beam construction and Scandinavian-inspired design make for a unique and cozy atmosphere.

Location · Family · Sleep quality

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.

Value · Family · Hiking

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.

Location · Family · Condition

Modern Secluded Retreat

Escape to the center of 11+ acres of woods, water, and dark starry skies—under 2 hours from NYC. Walls of windows pull the outside in, with a stream, pond, and constant wildlife just beyond. Warm up by the fireplace, unwind in the open living space, and sleep deep in a king bed. A large jetted bathtub, bonus half bath, and a flexible bonus room with pool table and ping pong table on heated floors round it out. Peaceful, private, and made for slowing down.

Family · Location · Air conditioning

Custom Designed Catskills Retreat - Guest Favorite

Custom-designed private retreat. Nestled away from the noise, our peaceful haven offers nearby hiking and welcomes regular visits from deer, turkeys, and an array of unique birds. Open kitchen and living room with 14' ceilings and sweeping skyline views. Cook, relax, or work remotely in a bright, spacious environment where nature meets modern convenience. Life is good. Please note: This is not a home for parties, loud gatherings, or disrespectful behavior.

Location · Outdoor spaces · Amenities

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.

Value · Family · Condition

Sleep Above the Alpacas Scenic Farm Getaway

Slumber comfortably atop our 100+ alpacas, Angora rabbits, chickens and potbelly pig named Daisy. BuckBrook Alpacas offers a 3-bedroom loft apartment rental above our barn. You will sleep surrounded by the mountains and the animals on one of the highest peaks of the county. Wake up for a complimentary farm tour and enjoy a 10% off shopping pass in our farm store on our entire selection of alpaca gifts for the whole family.

Family · Value · Walkability

Stunning Peaceful Lakeside Cottage

Welcome to our cozy lakeside cottage in Roscoe, NY, bordering the spectacular Catskills! Located on a 180-acre private estate, it’s the ideal retreat only a few hours from New York City. It makes a perfect base camp for exploring the western Catskills and relaxing, enjoying the beauty of our property. The cottage offers a compact full kitchen, king size bed, well appointed living room, deck, and lakeside stone patios.

Value · Family · Cleanliness