Guest house holiday rentals in Sullivan County

Magical Catskills Guesthouse. Pool & private lake!

One-of-a-kind magic in the Catskills at “Casa del Monte” — a secluded, luxuriously appointed living space on 10 manicured acres of private land and water. Lake swimming, kayaking, paddleboarding and fishing on property! 5-minute walk from Loch Sheldrake lake and 15-25 minutes’ drive from the area's finest hiking, F&B, and entertainment — including Livingston Manor, Mountaindale, Callicoon, Roscoe, Beaverkill River, Willowemoc, Napanoch, White Lake, and Bethel Woods. 45 minutes from Woodstock.

Value · Family · Nearby

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.

Location · Value · Grill

Charming Brook Side Retreat by The Forest Reserve

Kick back and relax in this spacious, renovated XL studio in Smallwood, NY. Located by the tranquil bubbling Brook and surrounded by the Smallwood Forest Reserve, this guesthouse blends modern, vintage, and rustic decor, featuring a comfortable King-size bed. Just 93 miles from NYC, it’s minutes from Bethel Woods Center for the Arts, scenic lakeside dining, lake beaches, and hiking trails. As a Superhost, I’m thrilled to welcome you to my cozy retreat for a peaceful and memorable getaway!

Location · Outdoor spaces · View

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.

Family · Location · Heating

Beautiful Mtn Cozy Cabin-183 acres-Amazing Views

Bethel Woods & Callicoon Hills so near. Truly beautiful mountain cabin. Artistic, eclectic, luxurious—hi-speed internet—private patio & picnic table—comfy beds, bathrooms with 2 person Jacuzzi tubs—house-wide stereo—induction cooking–air-fryer/oven—dishwasher— linens–snacks-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!

Value · Location · Wifi

Pangri-La

Looking to connect with nature in a calm, quiet, and stylish loft? Look no further than the Pangri-La! You'll have privacy, mountain views, and more. You will enter through a private entrance, go up a flight of stairs, and you'll find our airy open-concept loft. It's equipped with a king-sized bed as a well as a queen-size pull-out sofa bed. We are dog friendly, situated close to Minnewaska State Park for hiking and swimming, and only a 5 min drive to access amenities in Ellenville.

Location · Family · View

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.

Location · Family · Decor

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.

Value · Location · View

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.

Family · Location · Hospitality

Garden Cottage | Hot Tub, Firepit, Outdoor Shower

A serene escape for couples or solo creatives — slow mornings, forest views, and evenings in the hand-built cedar soaking tub. • Fire pit & forest patio • Queen bedroom w/ sliding doors to woods • Kitchen (induction stove-top, air fryer, coffee & tea) • Outdoor shower & Hot Tub • 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.

Location · Bathroom · Decor

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 separate bedroom. Just 1.5 hours 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 work for someone needing to finish a project or anyone wanting a peaceful respite.

Value · Family · Kitchen

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!

Location · Quiet · Pets