Holiday houses in Highland

Forest Art House • Spacious • Hot tub • Firewood

Escape to a stylish Catskills home in Eldred, NY. Nestled among trees, this chic retreat features modern furnishings, art-filled walls, and a cozy living room with a big-screen TV, games, and an electric fireplace. Sunlight pours through large windows illuminating spacious bedrooms with comfortable beds and scenic views. Cook in a fully equipped kitchen, dine indoors or on the deck, and unwind by the fire pit or nap in the backyard hammock. Perfect for a peaceful getaway with family or friends

Family · Location · Bathroom

Luxury Container | Hot Tub | Rooftop Tub | Pizza

Escape to a one-of-a-kind luxury container home nestled in the Catskills, featuring a year-round hot tub, rooftop soaking tub, outdoor kitchen, pizza oven, and peaceful forest views. Escape the ordinary and immerse yourself in this stylish 3-BR container retreat. Designed with sustainability and creativity in mind, our container home offers a one-of-a-kind lodging experience for those seeking a blend of innovation & relaxation. Book today and experience container living! Message me for Q's

Family · Value · Parks

Remote Waterfall Cabin at Swiftwater Acres

Deep in a lush oak forest, on the bank of Bushkill Creek sits this hidden oasis. This is simply THEE most private abode in the entire area. Situated just feet from the water, the falls can be seen and heard from every room within the cabin’s charming, rustic interior. This spectacular 45 acre parcel is set within a vast reserve of state land: an oasis within an oasis. Just 90 minutes from NYC, this is a truly sublime atmosphere, perfect for those seeking a rejuvenating and inspiring getaway.

Location · Family · Pets

Enchanting River A-Frame|Fire Pit| Magical Forest

Escape to our Magical Riverside A-Frame on 4 secluded acres. Swim in the enchanting river, grill dinner under the trees, and gather by the fire pit beneath twinkling string lights & a sky scattered with endless stars. Watch deer, eagles & fireflies as you unwind in this cozy 2BR cabin. Perfect for couples, nature lovers, and anyone craving a peaceful retreat. Minutes from scenic hikes & Delaware River adventures connecting deep with nature - leave feeling like you stepped out of a storybook.

Value · Family · Wi-Fi

Luxury Catskills Cabin | Private Sauna | Lakes

Welcome to Parkside Den, a private forest retreat created for guests who appreciate clean non toxic living, thoughtful design and genuine quiet. Set near the Delaware River and several public lakes, the cabin is focused on wellness and comfort. Enjoy organic Avocado mattresses, HEPA-purified air, AquaTru filtered water, Branch Basics, Public Goods, Purity Coffee and non-toxic products throughout. Outside, unwind in your private sauna, gather around the firepit or relax beneath the trees.

Family · Location · Accuracy

Dog friendly, heated pool & Hot Tub w/ fenced yard

Escape to a modern mini barn 7 mins from Narrowsburg with a heated pool, hot tub, fire pit, high-speed Wi-Fi, Ev charger, backup generator and a fully fenced yard for your pups! Set in the gorgeous Hamlet town of Narrowsburg, my home is a 5 min drive into Narrowsburg Main Street! Bethel, Callicoon, Barryville, Livingston manor, are all 25 mins away. If you're looking to ski Big BEAR Mountain is close by! High speed internet 500mps. 7 day bookings and monthly bookings receive discounts!

Value · Location · Nearby

Little River: Waterfront Sauna & Chic Log Cabin

Escape to Little River, a stunning log cabin sitting along a mountain stream in the southern Catskills, just 2 hrs from NYC & 2.5 from Philly. This 2-bed, 1-bath cabin boasts authentic countryside charm, modern amenities & outdoor delights like a riverfront sauna, creekside dining & firepit. Perfectly designed for spending time with friends, working & relaxing - Little River is your perfect upstate escape! Nearby towns: Barryville (3 min), Narrowsburg (25 min), Forestburgh (30 min)

Family · Location · Wi-Fi

Forest Spa Retreat on Cascading Brook • 90 Min NYC

Tucked into an evergreen forest, The Water House is a private spa retreat set above a cascading brook—where flowing water shapes your stay. Spend slow mornings on the deck, unwind in the hot tub, and gather by the fire pit under the stars. Find a quiet moment beside the Japanese-inspired pond. Inside, soft textures and vintage style create a warm, calming atmosphere designed to reconnect you with nature while offering the restful comfort of a boutique retreat.

Location · Family · Barbecue

The Fern Hill Lodge | Serenity on 20 Private Acres

The Fern Hill Lodge is a lovingly restored retreat, crafted by a local master carpenter and designed for families, couples, or friends ready to escape the city and reconnect with nature. Just two hours northwest of NYC, our private, secluded rustic sanctuary is tucked away on a lush, ferntastic hilltop — a hidden gem nestled on 20 peaceful acres. Whether you’re here to explore, rest, or simply breathe, the entire house and land are yours to enjoy.

Location · Family · Decor

Private Riverfront Catskills Retreat w/ Hot Tub

Tucked away on a private stretch of riverfront in the western Catskills, this cabin was made for unforgettable summer days. Morning coffee on the deck, afternoons by the river, golden-hour dinners outdoors, and fires under the stars. Inside, expansive picture windows, warm mid-century interiors, and thoughtful details create a space that's equal parts design-forward and deeply relaxing. Perfect for couples, families, friends, and dogs.

Value · Location · River

Upper Delaware River cottage

1930's cottage with spectacular views. Fully stocked and situated on a stretch of Upper Delaware river rapids near Narrowsburg, NY. Heat/AC system, fireplace, solo stove, barbecue and porch. There are 7 acres with river views and access . River is a couple hundred yards from cottage, lots of lawn, hammock, kayaking, lawn games, board games, hiking, fire pits, lots to do or just relax.

Location · Family · Pool

@TheHighlandBungalow - Sullivan Catskills Getaway

As featured in Dwell, GQ, Vogue, and Field Mag -- The Highland Bungalow is a fully renovated 1950's cabin in the New York Sullivan Catskills. Whether it's the lake views, fire pit, and BBQ summer life you're craving, or the hot cider filled cozy nights around the wood stove — this sun-filled getaway is fully equipped with everything you could need for a relaxing stay.

Family · Location · Heating