Guest house holiday rentals in Sullivan County

Historic Winery Farmhouse by Lake

For an unforgettable escape, stay at the Hammer House at Three Hammers Winery, a beautifully restored 1820 historic farmhouse blending classic charm with modern comforts. This inviting retreat features a fully equipped kitchen, spacious living areas, and cozy bedrooms, all complemented by a covered porch overlooking a scenic pond and vineyard, plus a patio with a fire table for relaxing evenings. Its prime location offers easy access to the Pocono Mountains. Relax, Fine Wines, Beautiful scenery!

Woodland Cottage Escape | Cedar Hot Tub | Firepit

A serene escape for couples or solo creatives — slow mornings, forest views, and evenings in the hand-built cedar soaking tub. • Cedar tub under the stars • Fire pit & forest patio • Queen bedroom w/ sliding doors to woods • Kitchen (induction stove-top, air fryer, coffee & tea) • Outdoor shower (seasonal) • Shared property w/ main house; the cottage & patio are your private spaces • Minutes to Narrowsburg shops, hikes & Delaware River Perfect for quiet inspiration or a romantic weekend away.

Willow House Cottage

Sunny guesthouse with plenty of privacy in Mountaindale, Sullivan County, 2-hour drive from NYC. 3 bedrooms, open plan living room/kitchen and dining room, barbeque area, etc. Wooded setting, spacious yards behind Main House; stone walls and gardens, fish pond and surrounding forests, variety of wildlife. Magically quiet. Vegetable, herb + berry gardens. 10-minute walk to lake and canoe. 1 mile from village. Only living room/kitchen has AC. Other rooms have fans. Avail. April - early Nov.

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.

Wonderful getaway place in the Catskills!

Enjoy this nice getaway cozy place with your friends and family with a private deck on a beautiful property hosted by a mother-daughter team! Just under 2 hours from New York City! This two-bedroom apartment includes a new kitchen, and living/dining room with a sofabed and accordion doors so it can be turned into a third bedroom for a night. There is also a comfy sitting area with a smart TV. This place is a part of a bigger house. Dogs are ok. We have cats in our part of the house.

Mondrian Manor

Welcome to the Mondrian Manor in the lower Catskill mountains. This stylish, quiet getaway is a freestanding cottage that includes a private deck and a separate bedroom. Just one hour and forty-five minutes from New York City it has access to many hiking trails, Sam's Point/Ice Caves, Blue Cliff Monastery, unique eateries, and concert venues including Bethel Woods. With a comfortable workspace it will be great for someone needing to finish a project or anyone wanting a peaceful respite.

Indigo Bunting Farms MilkHouse/Sauna & Cold Plunge

We invite you to enjoy our renovated guesthouse, once the milk house on a productive dairy farm in the mid-twentieth century. Our secluded property is on a peaceful country road, yet central (~15 minute drive) to the main streets of Callicoon, Livingston Manor, Roscoe, and Jeffersonville, all worthy of exploration. The kitchen is fully stocked and capable and, once on the property, you are welcome to roam its 12 acres, enjoy the fire pit, wood-fired sauna and cold plunge.

Private River Access, Beaverkill

Escape to our riverside retreat in the Catskills! This private, detached home offers 2 bdrms, 3 twin beds, 1 queen and a full futon. Enjoy exclusive access to Beaver Kill River and a stocked pond with kid-friendly fishing. WiFi, TV, full kitchen, and board games provide comfort and entertainment. Relax on the new deck overlooking the river or gather around the firepit with beautiful chairs. Just 15min from downtown Roscoe's dining, bars, and breweries. Unplug and unwind.

Woodland Loft + Outdoor Kitchen in the Catskills

🍎 Welcome to Wild Apple Woods 🦌 An enchanting wooden loft with one queen and one double bed in a cozy, open layout. Tucked away on 20 private acres, the space features a covered outdoor kitchen, hot shower, compost toilet, hammock, picnic table, and fire pit. Sleeps 4 adults comfortably, with additional seating on a loveseat and sofa. Great for wildlife watching, stargazing, and unwinding near swimming holes, hiking trails, and some of the best dining in the Catskills.

Beautiful Mtn Cozy Cabin-183 acres-Amazing Views

Truly beautiful mountain cabin. Artistic, eclectic, luxurious—super hi-speed internet—private patio & picnic table—comfy beds, bathrooms with 2 person deep Jacuzzi tubs—house-wide stereo—induction cooking–air-fryer/oven—dishwasher— linens–snacks and drinks included. Geothermal heat/hot water, solar electric — EV charging. Private chef and masseuse available. Farm-to-table restaurants, skiing, hiking, bike rentals, tons of trails, fishing and 183 acres to explore!

Map Maker's Cabin

All season private, cozy cabin in a peaceful woodsy oasis, 15 min from Delaware River; off a main road and close to many peaceful walks. Fast wifi for working remotely, writer's retreat, romantic getaway, meditation, yoga, or time in nature. **We have an (inflatable) hot tub which we fill for guests (unless temps are way too low). NOTE: all-wheel/four wheel drive is highly recommended during winter months. We are looking forward to hosting you!

Hiker’s Haven, a Cozy Cabin above Bashakill Refuge

Just 90 minutes from NYC, Wurtsboro is a charming and tranquil Catskills retreat. Hiker’s Haven is a cozy, detached Loft on the same property as our log cabin home, set above the Bashakill Wildlife Refuge. While trees block direct water views, you’ll hear birdsong and may spot bald eagles or red-tailed hawks. In fall, glimpses of the Bashakill emerge through colorful foliage. Enjoy hiking, fishing, glider rides, and local shops and galleries.