Guesthouse vacation 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.

Location · Value · Pool

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.

Value · Location · Kitchen

Garden Cottage | Hot Tub, Firepit, Outdoor Shower

A serene escape for couples or solo creatives—think slow mornings and evenings relaxing in our hand-built cedar soaking tub. • Fire pit, gas grill, & private forest patio • Well-equipped kitchen (induction stovetop, air fryer, coffee & tea) • Outdoor shower & Cedar Hot Tub • Shared property w/ main house; the cottage & back patio are your private spaces • Minutes to Narrowsburg shops, hikes & the Delaware River Perfect for quiet inspiration or a romantic weekend. IG: @HomesteadGardenCottage

Location · Hiking · Hot tub

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 · Getting around

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!

Family · Value · Kitchen

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.

Family · Location · Accuracy

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.

Family · Location · Quiet

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 · Heating

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 · Family · Sleep quality

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 · Bathroom

Charming Brook Side Retreat by The Forest Reserve

Escape to this romantic, renovated, spacious 550-sq-ft studio where a babbling brook lulls you to sleep, surrounded by the quiet of Smallwood Forest Reserve. Unwind by the fire pit any season, or explore hiking trails, lake beaches, and Resorts World Catskills casino, water park, and restaurants , just 10 minutes away. Under two hours (93 miles) from NYC, minutes from Bethel Woods Center for the Arts and scenic lakeside dining. Superhost welcome.

Location · Value · Comfort

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.

Location · Family · Hiking