Holiday houses in Denning

Spacious Catskills Farmhouse w/ In-Ground Pool!

Come take a dip in our 8' deep in-ground pool and enjoy summer in the Catskills! There is so much to do here! Relax at a spa, try your luck at the casino, go for a hike, or shop at a local Farmer's Market. Enjoy our grounds with a hike on the property, a BBQ in the backyard, or roast marshmallows by the firepit. You will feel right at home in this charming & restored 5BR farmhouse. Located on 5+ acres near the great Catskills Forest Preserve, this is a great place for four season recreation.

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.

Dreamy Catskills mountain getaway w/ yoga studio

Recharge and unwind in this gorgeous space nestled in the woods. The Mountain Terrace has an indoor wood stove, a deck with a beautiful view, a fire-pit, 3 bedrooms and 2 bathrooms. This stunning house has been recently renovated and offers total privacy and serenity - sitting on 5 acres at the end of a quiet road. There is a washer/dryer, a dishwasher an artist cabin and a yoga studio. An easy 15 min drive to Livingston Manor for great restaurants, shopping and activities. Pet friendly.

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.

Modern Riverside Retreat with Firepit, Hot tub

Come enjoythe oasis on the pristine headwaters of the Neversink River with huge backyard, river access, and great kitchen amenities. Offers four bedrooms, and two large baths with bright, sunny living areas. You won't be roughing it! We have a large outdoor stone firepit surrounded by Adirondack chairs, a hot tub, quiet trails for private walks, and all the nature you love. There are three outdoor seating areas for meals and relaxation, a woodstove, and a picture perfect kitchen.

Modern Catskills Tiny House Near Hiking Trails

A modern and well- designed home located in the Neversink area of the Catskills. The Tiny House has been updated with high-speed 200 Mbps wifi and a separate landline. There is no cell phone service in the immediate area. The house is a short drive to some of the best hiking trails in the area. Enjoy walks in the woods, country drives, or relax on the deck overlooking the pond. 3- night minimum stay. We require our guests to be 24 and over. Maximum of 2 adults. No pets .

Gingerbread House- a 1950s Catskills Chalet

Perched high among the trees, Gingerbread is a 1950’s Swiss chalet that sits on 4 acres. This is the house everyone slows down for, points and says ‘ that’s the house I would want Upstate’. Well ….she's taken. But I am so happy to welcome you as guests for a short period of time. Gingerbread comes with all the little touches making it feel like the perfect home away for a week, weekend or however long you can escape your regular life.

The Blue House on the Hill Catskills

Spectacular Mountain & Valley Views—Streamside. A beautifully renovated getaway located in the heart of the Catskill Mountains. Upon entering this gorgeous retreat, you will be instantly taken by the designer's attention to detail. Enjoy the open floor plan kitchen with soapstone countertops overlooking the amazing vaulted great room with spectacular views of the farm, valley, and surrounding mountains.

Modern creekside cabin in the Catskills

Welcome to our peaceful little cabin, designed for full immersion in nature. Lounge by the creek, gaze out XL windows, or cozy up by the fire—every detail invites you to slow down. Tucked on a quiet road just minutes from hiking trails and Willowemoc fly fishing, we’re also only a winding 15-minute drive to charming Livingston Manor—a quintessential Catskills town—and less than 2 hours from NYC.