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.

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.

Gorgeous Waterfront w/ Hot Tub and Game Level

Hi, I’m Anna. I’m so glad you’re here, and I’d love to welcome you to The Glass House! Here are a few things I think you’ll especially enjoy about the house. Highlights – You’ll love the: Peaceful waterfront setting – tucked away on the lake, yet just minutes to town Year-round hot tub – the perfect way to unwind after hiking, or exploring Family-perfect layout – two spacious levels with a game/media room and screened porch Kayaks & life vests – easy, safe access to the water for all ages

River House at Trout Town Farms

Fully furnished River House with private access to the famous Beaverkill River Lower Mountain Pool. You can walk through a real working farm as well as taste the seasonal harvest when available. Here you can take a farm tour and visit with our resident animals, including alpacas, Nigerian dwarf goats, rabbits, and chickens. Whether it's fishing, relaxing by the fire, or sitting on the patio listening to the river, this farmhouse offers a peaceful retreat for the whole family to stay.

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.

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.

Bird Spring Hill Guest House

This sunny studio apartment surrounded by woods and farmland is perfect for your country getaway. The newly renovated space has modern amenities, farmhouse charm and a deck with a lovely view. Nestled on a quiet road in the hamlet of Long Eddy, there's lots to explore-- tubing & fishing in the Delaware River, hiking trails, swimming in nearby lakes, horseback riding, Callicoon's restaurants & farmer's market, tastings at the local distillery and so much more!

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.

The Cabin at Pleasant Valley Farm

The cabin is located on a dirt road on our farm with a beautiful pond and an amazing view! This off-grid, cabin has two queen beds (100% cotton sheets), a mini-kitchen with a battery-ignition gas range, solar powered refrigerator, solar lighting, a wood stove, an outdoor shower, a fire pit, and an old-fashioned outhouse. An expansive porch and dock provide comfortable outdoor living. A seasonal favorite, the cabin is available May-Sept.

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.