Holiday rentals in Handsome Hollow

Victorian Luxury in the Catskills

Beautifully restored 1860s Victorian house, perched above a cascading river in picturesque Sullivan Catskills, near Callicoon. The Henderson features 4 comfy bedrooms, impressive living & dining areas, chef's kitchen, vintage bathrooms + clawfoot bathtubs, high ceilings, rustic & refined decor. A Japanese Onsen like hot tub, outdoor shower, 2 fire pits, 2 ponds & 9 acres provide the most perfect Catskills getaway. Mins to Callicoon, close to Livingston Manor, Roscoe, Narrowsburg, Bethel Woods.

Luxury Home:Heated Pool, Sauna, Hot Tub & C Plunge

Pool Open to Thanksgiving! Orchid Home is a thoughtfully curated wellness retreat designed to restore balance, calm the mind, and elevate the experience of simply being present. From the moment you arrive, the home welcomes you with an immediate sense of ease, where natural light pours in through expansive windows and gently fills each room. The architecture and interiors work in harmony, blending modern design with soft elements that create a space that feels both refined and deeply comforting.

Wonders Never Cease: Peaceful Cabin with Wow Spa

Welcome to Wonders Never Cease, my upscale log cabin sanctuary & private spa, perched on a hilltop amid 12 acres of forest, with a spring-fed pond, incredible stargazing & your own hot tub, cold plunge and sauna. Ideal for romantic getaways, family vacations, trips with friends, wellness retreats - anyone craving a reset in nature. Wonders Never Cease is far more than a typical Airbnb cabin. It’s a destination in itself—and 1 in 5 bookings are returning guests. We love hosting, and it shows!

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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.

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Cabin@Crow Hill: unplug and reconnect with nature

Escape it all, listen to the birds and near by Buck Brook. Explore the Catskills with plenty of hiking, lakes, and fly fishing. The stars are incredible, so as you sit on the balcony or at the fire pit look up. Crow Hill is located on a quiet road away from the bustle of town. The wifi is moderate due to the location, so it allows you to unplug. Crow Hill is dog friendly ( no cats) and perfect for a family getaway. The cabin is deep cleaned and sanitized between guests. Come take a break!

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.

Spectacular River Front Custom Log Cabin

Foot steps from the crystal clear Delaware River perfect for fishing, swimming, kayaking, hiking, golfing canoeing or just sitting with your feet in the water enjoying the view! This 2000sq foot custom log home is located on a private road directly on the Delaware River in the heart of the Catskill Mountains. 2 1/2hours from New York City. The location is the best the Catskills has to offer! Nothing in the area compares to the location or the interior design. Truly 5 star accommodations!

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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.

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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.

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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.

The River House with Hot Tub

Bring the whole family to our dream home on the main branch of the Delaware River! We have eight bedrooms and 13 beds. The basement is an awesome game room with pool table, shuffle board, ping pong, and plenty of games. Dining table seats 16+… the perfect spot for friends and family to gather. Nice view of the river from the hot tub. River access is just a short walk down a pathway on this 2.8 acre property, where you can fish or launch your tube, kayak, or canoe!

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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.