Holiday houses in Handsome Hollow

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Top-rated holiday rentals in Handsome Hollow

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
The A-frame cabin is surrounded by vibrant autumn foliage, showcasing hues of gold and orange. A welcoming red door stands out against the green exterior. A wooden deck extends from the cabin, providing an inviting entry point amidst the natural landscape.
Cabin in Margaretville
5 out of 5 average rating, 268 reviews

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.

Superhost
A tiny cabin with a unique Japanese-inspired design is nestled among tall trees, accompanied by a gravel pathway and a small fire pit. The cabin's natural wood exterior blends with the forest surroundings, creating a serene atmosphere beside a flowing brook.
Cabin in Downsville
4.87 out of 5 average rating, 350 reviews

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.

Top Guest favourite
A private deck area features a wooden chair beside a neatly stacked pile of firewood. The entrance displays a large sliding glass door, illuminated from within, revealing a warm interior. Soft outdoor lighting complements the natural surroundings of greenery.
Tiny home in Livingston Manor
4.97 out of 5 average rating, 182 reviews

Element House - Off Grid Hideout

Unwind and reconnect with nature in this rustic and comfortable retreat nestled at the edge of a blueberry field. Surrounded by serene Catskills countryside, you’ll feel a world away, yet still be just minutes from outdoor activities, a thriving food scene, and Bethel Woods just 35 min away. Inside, you’ll stay cool with AC, a cozy queen bed, kitchenette, dining table, reliable wifi, and full bath. Outside, relax by the fire pit or cook on the charcoal grill. We are an LGBTQ+ inclusive space.

Top Guest favourite
The A-frame cabin is nestled among trees, featuring a wooden deck and wide glass doors that open to the interior. A private hot tub is positioned nearby, providing a relaxing outdoor space surrounded by nature.
Cabin in Damascus
4.99 out of 5 average rating, 273 reviews

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.

Top Guest favourite
A spacious living area features a sectional sofa adorned with patterned cushions. Two wooden side tables sit on a plush area rug, while natural light enters through a window framed by light curtains. A rustic paddle and framed artwork decorate the walls.
Home in Roscoe
4.95 out of 5 average rating, 141 reviews

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.

Guest favourite
Chalet in Obernburg
4.97 out of 5 average rating, 245 reviews

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.

Top Guest favourite
Home in Narrowsburg
4.92 out of 5 average rating, 145 reviews

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.

Guest favourite
A rustic cabin is nestled among lush trees, featuring a metal roof and warm, inviting windows. Soft lighting from the windows enhances the natural surroundings, while a stone walkway leads to the entrance, blending harmoniously with the forest landscape.
Place to stay in Downsville
4.88 out of 5 average rating, 236 reviews

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.

Top Guest favourite
A serene cabin is situated next to a tranquil pond, reflecting the surrounding greenery. The dock extends into the water, offering a peaceful outdoor space. The area features a well-maintained lawn with tall grasses, enhancing the natural setting.
Cabin in Callicoon
4.99 out of 5 average rating, 220 reviews

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.

Guest favourite
A serene lakeside area features two wooden platforms extending over calm waters, framed by lush trees. A black wooden bench sits nearby on a stone path, surrounded by autumn foliage reflecting the warm hues of the sunset.
Cabin in Roscoe
4.97 out of 5 average rating, 72 reviews

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.

Guest favourite
The exterior of a geodesic dome house is shown at dusk, surrounded by trees. A private deck with ambient string lights extends from the structure, featuring large windows that invite natural light. The entryway is framed by a staircase leading to the deck.
Dome in Livingston Manor
4.95 out of 5 average rating, 60 reviews

Dome House with Catskill Views!

Escape to a one-of-a-kind Geodesic Dome nestled atop Shandelee Mountain. This fully renovated 2-bedroom retreat with a bonus loft offers enchanting Catskills views, a private deck with mountain vistas, and cozy wood stove. Just minutes from Livingston Manor's charming Main Street, enjoy modern comforts with rustic charm. Perfect for remote workers, nature lovers, and those seeking a peaceful mountain getaway.

Top Guest favourite
An aerial view showcases Amber Lake Cottage set against the backdrop of vibrant autumn foliage. The cottage features a spacious lawn leading to a dock on Amber Lake. Calm waters reflect the trees, while a rowboat rests nearby, indicating opportunities for outdoor activities.
Cottage in Livingston Manor
4.96 out of 5 average rating, 447 reviews

Catskills Modern Amber Lake Cottage

Featured in the NY Times, Amber Lake Cottage is nestled right on the bank of Amber Lake in Livingston Manor, NY. Just 2 hours from the bustle of your 9-5 in NYC, the home lets you catch your breath. Sleep in. Rowboat. Fix a drink by the fire. Dance to a record. Experiment with local produce in the chef's kitchen. See the stars above you. Hear quiet for the first time in months.

Popular amenities for Handsome Hollow holiday rentals