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.

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.

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

The Farmer's Daughter - Callicoon/Livingston Manor

This house! This pool! This outdoor shower. The bald eagle’s nest 100 yards from the front door!!! The Farmer's Daughter House is nestled on 60 acres of private trails, meadows and forests with a saltwater pool overlooking the hills of historic Rock Valley. Located just 120 miles from New York City and 15 minutes from vibrant and lively Callicoon NY. Enjoy our home in privacy with friends and family, just as we love to do. Looking forward to hosting you. IG: @thefarmersdaughterhouse

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. Please note: This is not a home for parties, loud gatherings, or disrespectful behavior. *Avail for monthly rental at a discount

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.

Burnwood Cabin | Creekside Bliss

Four miles off Route 17, across a green truss bridge over the Beaver Kill, this '50s-era cabin on the creek will be your home as soon as you ease down the driveway from Burnwood Road. On the bank of Trout Brook, this simple, perfectly appointed lodge is quintessential Upstate NY -- secluded while accessible to Roscoe, Livingston Manor, and other popular city getaways. East Branch sits in the fly-fishing epicenter, with countless access points to the Beaver Kill and Delaware rivers.

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.

Roscoe Retreat

Located in Trout Town USA ! Secluded, 1600 sq ft log home, 3 bedrooms, 2.5 baths on 5 private acres. Magnificent year round Catskill Mountain views. Beaver kill River is 5 minutes away! Stunning indoor fireplace, relaxing front porch and large back deck with gas BBQ. Internet and satellite T.V. in bedrooms, with Netflix and HBO. Spacious outdoor, w/ gazebo, hammock , picnic table & hot tub! Less than 2hrs from 2hrs from the GWB this is a great year round getaway!

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.

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.