Holiday houses in Handsome Hollow

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Top-rated holiday rentals in Handsome Hollow

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Top Guest favourite

Home in Downsville

4.98 out of 5 average rating, 132 reviews

Trout fishing on the Delaware

Beautiful Private area 2 homes on 10 acres, you will have one, newly built with all amenities, on the river, great fishing, luxurious accommodations, fire stove, local town full size pool with full access, pond / beach with boating, local Knack/ Canoe rental on the East branch of the Delaware River all within 20 minuets. Local antique shops, fairs and markets, Enjoy the Catskills Today. The property boarders the River Just a walk Away. Great for Family and Children. Local food, Shopping and fun

Superhost

Cabin in Downsville

4.88 out of 5 average rating, 240 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.

Guest favourite

Cabin in Wurtsboro

4.97 out of 5 average rating, 331 reviews

Spring Spa on a Cascading Brook - The Water House

The brook flows through an evergreen forest creating a nourishing environment and the perfect setting for a relaxing and rejuvenating spa retreat. The living/dining room, hot tub/deck, and gas fire pit are set overlooking the cascading brook, ideal for entertaining, meditating or simply as an enjoyable natural muse. The soft, cozy and elegantly vintage styled interior is illuminated and warmed with central heating, ambient lighting and a home surround sound entertainment system with karaoke.

Top Guest favourite

Cabin in Damascus

5 out of 5 average rating, 100 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

Home in Jeffersonville

4.99 out of 5 average rating, 188 reviews

BirchRidge A-Frame: Sauna/Firepit/Hiking/King Bed

Nestled in the Catskills Forest, less than 2 hrs from NYC you'll find Birch Ridge A-frame! This gorgeous 2 bedroom cabin is set on 6 private acres with hiking areas and a seasonal stream. Enjoy the wall of windows that create a magical stay with breathtaking views. This is the perfect place to relax, sit in the barrel sauna, hike through the private forest, roast marshmallows over the fire, and soak up the sounds of nature. A space that’s made for creating memories that will last a lifetime!

Guest favourite

Cabin in Roscoe

4.99 out of 5 average rating, 136 reviews

Wonder's Never Cease: Hot Tub, Sauna & Cold Plunge

Hi, I'm Wonder! Welcome to my magical Catskills cabin escape - quiet & with a private spa. Ideal for romantic getaways, vacations w family & friends, or wellness retreats. Nestled in nature, our clean log cabin offers a natural, chemical-free hot tub, sauna & cold plunge. Enjoy views from the porch, cozy by the wood stove, grill epic meals, indulge in the spa & explore hikes & cute towns. Child, infant, pet friendly. Helpful host! Book to reconnect with nature, one another & yourself.

Guest favourite

Home in Livingston Manor

4.93 out of 5 average rating, 140 reviews

Parkston Schoolhouse

Relax and unwind in this historic converted one-room schoolhouse. Built in 1870, the Parkston Schoolhouse served all grade levels in the Livingston Manor area. The schoolhouse was retired and converted to a cozy cottage style home in the mid 20th century and has recently been renovated into a stylish tiny home getaway. The home is tucked into the hillside along the beautiful, winding Willowemoc Creek and is set amidst a lush Catskill landscape just a five minute drive from Livingston Manor.

Guest favourite

Cabin in Walton

4.94 out of 5 average rating, 155 reviews

The Mill House: Creekside Catskills Spring Escape

Nestled in the heart of the Catskills and just a 2.5-hour drive from NYC, escape to a winter retreat where you can reconnect with nature and enjoy the serene beauty of the season. This historic gem underwent a meticulous restoration in 2021, 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.

Top Guest favourite

Home in Equinunk

5 out of 5 average rating, 168 reviews

Art House Bird Sanctuary at EBC Sculpture Park

The Art House is set in a Sculpture Park being Developed by the artist Tom and Carol Holmes. The Park is 38 acres of rolling hills, grass land with valley views, bordered by two streams and woodlands. The views are magnificent. The house is set on the second tier of three rolling hills 1000 feet up from the road. The property is the newest building project/ABNB offering from Tom; who creates magical and life changing experiences...in the landscape; at EBC Bird Sanctuary Sculpture Park.

Superhost

Home in Roscoe

4.87 out of 5 average rating, 123 reviews

Modern Rustic Tiny Home in the Catskills

Enjoy this tiny home nestled among five acres of Catskills Forest on a two home lot, just a short distance from essential Catskills towns like Roscoe and Callicoon. The house is a newly built modern studio with a sleeping loft, kitchen, bathroom, wood stove, and large sundeck. It has a separate driveway from the second house on the lot, to maximize privacy for you and your group. Enjoy the wifi, luxury furnishings, thoughtful amenities, and Smart TV in our retreat from the city!

Top Guest favourite

Tent in Livingston Manor

4.98 out of 5 average rating, 142 reviews

Milkweed Camp - Glamping in a Blueberry Field

Our off-grid canvas tent is situated at the edge of a meadow, surrounded by blueberry bushes. It's just 4.5 miles to Main St in Livingston Manor, and 35 minutes to Bethel Woods. We provide a full-size bed (w/ heated mattress pad), fire pit, firewood, propane heater, and solar power. You have access to a private outhouse with composting toilet & outdoor shower on-site, and a conventional shared bathroom if you preferred. We are an LGBTQ+ inclusive space.

Superhost

Place to stay in Downsville

4.87 out of 5 average rating, 180 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.