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.

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!

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

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!

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.

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.

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.

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!

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!