Barn vacation rentals in Sullivan County

Luxe Barn • Hot tub • Pond • Pet Friendly

Welcome to the Luxe 1850's fully renovated Barn with Pond & Hot Tub Experience unmatched luxury in this exquisitely designed barn featuring high-end furnishings, a private hot tub with stunning views, a fire pit, and a cozy indoor fireplace Enjoy the serene pond, breathtaking landscapes, and a gourmet kitchen. The expansive private outdoor area offers dining and relaxation spaces. Perfect for romantic getaways or luxurious retreats with friends & kids. The ultimate escape in nature's beauty

Farm guesthouse w views, trails and pond.

Escape the urban rush with a bucolic stay at this stylish guest house. Located on an 85 acre former dairy farm, the house sits amid lush meadows and dense woods that are waiting for you (and your pet) to explore. With stunning views of the mountain tops, you can swim in the pond, grill on the porch, snow shoe in the woods, warm up by the wood burning stove, take in the sunset, or visit the restaurants and stores of Livingston Manor or Roscoe. Local area boasts fly fishing and great hikes.

The Overbrook Studio

Looking for a getaway from the city for the fall and winter months? The Overbrook Studio is the perfect place to escape the city!. Just under 2 hrs. from NYC, it has everything you require to dwell in luxurious comfort. Driving onto the property, you are transported to a peaceful retreat, sometimes described as magical. Protected from the road by Hemlock trees and the gentle buck brook, the Overbrook Studio is the 2nd floor of what used to be the original barn of The Overbrook House.

Swimming Hole, New Hot Tub, Game Barn Coming Soon

Gorgeous views anytime of the year with a deep swimming hole in Callicoon Creek! Excellent trout fishing. Two creeks merge together on the property - it's quite spectacular! Relax on a boulder while reading a book. Cross the smaller side creek to our 7 acres of nature trails and feel like you're deep in a forest. Newly renovated, spacious house. FAST WiFi. Hot Tub. Firepit. Gas grill. Deck. 5 minutes to Delaware River, downtown Callicoon and Seminary Hill. Villa Roma 9 minutes.

Modern Scandi Farmhouse: sauna, trails, pond +90ac

This 90-acre former dairy farm has the most exceptional land with trails that cross huge meadows, woodland, and breathtaking panoramic views. The farmhouse, built in 1892, has a refreshing modern Scandinavian decor with four bedrooms, library, kitchen, living room and an enclosed patio for outdoor meals. In the garden shed, a hidden Finnish sauna awaits you. The pond, perfect for swimming, overlooks the mountains views. Two bikes available for nearby exploration.

Grand Refurbished Barn Full of Cozy Nooks

Runaway for a weekend upstate at this luscious, unique barn stay. The flexible space is great for a large group or a couple get away. Enjoy cozy nooks and spacious central spaces full of fun tidbits like a record player and fire pit. Light a fire in the indoor fireplace, or lounge bright silo in a hammock. With 9 acres of hiking trails on the property, this stay is perfect for those looking for some rest and relaxation, while still offering plenty of fun.

Barn in the 'Burg

Step into this light-filled, newly renovated river-town retreat. The Barn has been transformed into a cozy, stylish oasis with all the modern comforts. Inside, you’ll find a lush, open-plan studio with soaring 20-foot ceilings. Plan a romantic getaway for two. Your furry friends are welcome! Whether it’s a snowy winter or a starry summer night, it’s the perfect time to soak in the hot tub and gather around the fire pit.

Renovated Chalet with Hot Tub and Pond

Welcome to Winterberry Pond, our completely renovated converted barn which is nestled on 7+ private acres. This two bedroom, one bathroom home has a modern aesthetic, having undergone a comprehensive renovation in 2022, and a brand new hot tub added in 2025. Located just 10 minutes from Roscoe and 15 minutes from Livingston Manor, this spot is the perfect spot to explore all that the area has to offer.

Wildberry Farm 34 Acres, Swim Pond, Secluded

Nestled on 34 acres on a mountain ridge top at 1800 ft, our newly restored 1890s farmhouse is cozy for a couple or a family with kids, yet plenty of space for a two family share or friends' retreat. You'll enjoy a spring-fed swimming pond, greens from our vegetable garden, teeming wildlife, the cleanest well water you'll ever taste, and wildberries! Only 2 hrs from NYC