Barn holiday rentals in Sullivan County

12min to Del River & Callicoon/Inn at Tyler Hill 1

Just a 2 hr drive from NYC, Inn at Tyler Hill is a country escape where guests can embrace the simple pleasures that come with being surrounded by nature and only 10 min from the Delaware River. Guest enjoy complimentary daily farm to table breakfasts year round. We provide a seasonal (5/15-9/15) weekend dinner shuttle to/ from Callicoon (12min) & weekend happy hour round of drinks on our patio. We can arrange local activities & reservations. Our goal is for guests to feel cared for like family

12min to Del River & Callicoon/Inn at Tyler Hill 4

Just a 2 hr drive from NYC, Inn at Tyler Hill is a country escape where guests can embrace the simple pleasures that come with being surrounded by nature and only 10 min from the Delaware River. Guest enjoy complimentary daily farm to table breakfasts year round. We provide a seasonal (5/15-9/15) weekend dinner shuttle to/ from Callicoon (12min) & weekend happy hour round of drinks on our patio. We can arrange local activities & reservations. Our goal is for guests to feel cared for like family!

Swimming Hole, OMG Game Barn, Skiing Close By

Gorgeous views anytime of the year with a deep swimming hole in Callicoon Creek! 3,500 sq ft OMG Barn due for completion this spring! Excellent trout fishing. Two creeks merge together on the property - the most serene setting. Cross the 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 min to Delaware River, downtown Callicoon and Seminary Hill. Villa Roma 9 minutes (skiing, tubing).

Shandelee Lake Cabin & Boathouse Livingston Manor

Cozy Cabin on the lake. Great place to unwind alone or with family and friends. Go for a swim in the lake, fish or just sit and enjoy the view. Close to the Original Woodstock site and Beautiful Bethel Woods. We are close to great trout fishing access, hiking, and horseback riding. We have two local Breweries nearby and you don't want to miss a chance to go rafting on the Delaware River. We are located between the Hamlets of Roscoe, Livingston Manor and Jeffersonville. A great hometown vibe.

Fox's Den: Fun Catskills Home w/ Private Lake Lot

Escape to a 5 bedroom, 2.5 bath Catskills vacation home on 2 acres. Perfect for a large family or several smaller families traveling together. The home is filled with over 50 board games, puzzles, darts, Smart TV and Foosball. Enjoy the outdoors with Ping Pong, Volleyball, various lawn games, firepit, grill and more. Relax at your own private lot on nearby Lake Huntington, just a short 7 minute walk from the house offering a private dock, hammock, waterfront firepit, kayaks & paddleboards!

Beautiful Renovated Barn Perfect Catskill Getaway!

(Now with high speed internet!!) Set on over 50 acres, bordering a thousand acres of state land, this renovated barn is the perfect setting for a country getaway! Get away from the stress of everyday life and relax in this quiet country retreat. An opportunity to enjoy a hike in nature, read a book, relax by the wood stove, or watch the cranes on the pond. If you’re looking for a peaceful country setting within 30 minutes of some of the best Hudson valley has to offer, you’ve found it!

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.

Sleep Above the Alpacas Scenic Farm Getaway

Slumber comfortably atop our 100+ alpacas, Angora rabbits, chickens and potbelly pig named Daisy. BuckBrook Alpacas offers a 3-bedroom loft apartment rental above our barn. You will sleep surrounded by the mountains and the animals on one of the highest peaks of the county. Wake up for a complimentary farm tour and enjoy a 10% off shopping pass in our farm store on our entire selection of alpaca gifts for the whole family.

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.

The Zen Farmhouse

A LITTLE BIT OF HEAVEN - this charming Historic 1878 farm in the CATSKILLS MOUNTAINS sits on 8 acres overlooking fields and woods with two beautiful barns and large organic garden. Come & enjoy the beauty of nature & all the Catskills has to offer.