Holiday rentals 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.

Tiny glamping cabin with mineral spring hot tub

This off grid, alternative powered site is located towards the front of a large twelve acre estate, alongside a flowing brook. Elevated over a natural spring that flows year round, the Japanese inspired aesthetics of this private, tiny cabin sits perched atop a deck among the wooded trees overlooking the waterway the mineral spring feeds, but not before filling the in-ground, cedar lined, two person, bubbling hot tub heated with a wood burning stove. One of two glamping sites on the 12 acres.

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.

Vinyl Pines · Architect Cabin, Hot Tub + Sauna

Architect-designed retreat on 10 private acres — year-round hot tub, sauna, 30ft cathedral ceilings, and a curated vinyl collection, 5 mins from Bethel Woods. Unplug, unwind, and reset your rhythm at Vinyl Pines, a music-inspired getaway down the road from the original '69 Woodstock festival grounds. Set on serene forest with a private walking trail, creeks, and a secluded yoga platform, this upscale sanctuary invites you to spin vinyl by the fire, soak under the stars, and recharge in style.

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.

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.

Dreamy Catskills mountain getaway w/ yoga studio

This stunning house has been renovated and offers total privacy and serenity - sitting on 5 acres at the end of a quiet road. The Mountain Terrace has an indoor wood stove, a deck with a beautiful view, a fire-pit, 3 bedrooms and 2 bathrooms and a double high ceiling in the main living space. There is a washer/dryer, a dishwasher an artist cabin and a private yoga studio. An easy 15 min drive to Livingston Manor for great restaurants, shopping and activities. Pet friendly.

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.

Private River Access, Beaverkill

Escape to our riverside retreat in the Catskills! This private, detached home offers 2 bdrms, 3 twin beds, 1 queen and a full futon. Enjoy exclusive access to Beaver Kill River and a stocked pond with kid-friendly fishing. WiFi, TV, full kitchen, and board games provide comfort and entertainment. Relax on the new deck overlooking the river or gather around the firepit with beautiful chairs. Just 15min from downtown Roscoe's dining, bars, and breweries. Unplug and unwind.

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.

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.

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.