Holiday rentals in Samsonville

Woodstock Historic Artist Estate - The Pond House

Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

Peaceful Cottage-in Private 5-acre field

Modern cottage with large outdoor living area in a beautifully secluded 5-acre field. A quiet and romantic getaway centrally located to Arrowood Farms, Westward Orchard, Inness Resort & Golf, Butterfields, Ollie's, as well as local hiking including Minnewaska State Park and the Mohonk Mountain House. Escape to a calm and relaxing environment with updated amenities yet pet-friendly. Enjoy lounging and dining on the deck while watching the wildlife or simply roasting s'mores in the fire pit.

The Lily Cottage Guesthouse

Tuck up in a thoughtfully renovated 1950s one bedroom cottage, perfect for a solo or a couples Catskill getaway! Situated in a quiet hamlet, nights in are lit by starlight and serenaded by peepers. Perfectly hemmed in by the Ashokan Reservoir, hiking, and the rail trail. The interior features a mix of vintage furnishings along with modern comforts. A 20 minute drive takes you to Rosendale, Kingston, or Woodstock for shops, breweries and excellent dining. Town of Olive Registration # STR-22-23

Studio in Private Forest; Peace and Solitude

Set in a hemlock forest on a quiet country road, this newly redone and separate guest studio is a perfect getaway. Set on 30 private wooded acres, the property is bisected by a Class A trout stream. Guests have access to the shared pool Mon-Fri, but not Sat-Sun. The second floor studio has a queen size bed and a queen size sofa bed along with a private bathroom. There is Wifi, a television (ROKU). There is no kitchen, however, we do provide a microwave, dorm fridge and Keurig coffee machine.

The Black Dymond A Private Streamside Cabin

A 2.5 hour drive from NYC to a serene, private, woodland, streamside home. This cabin sits on the very edge of the Catskill Mountains. It's cozy, modern, and minimalistic with a touch of rustic elegance. All new appliances with all the cooking necessities, a comfortable bed with large screen smart tv, excellent wifi service, a romantic gas-powered fireplace and the most private back deck away from the world to get lost for a weekend in the beauty of the woods.*Now offering mid-week price deals!

The Laurel Cabin

Tucked away in the serene Catskill mountains, this charming cabin has undergone a recent top-to-bottom renovation. Located just a short 5-min stroll from the vast expanse of the 30,000-acre Sundown Wild Forest, you'll discover endless trails, picturesque waterfalls, and abundant wildlife to explore. Additionally, within a mere 20-minute drive lies the stunning Minnewaska and Mohonk. We warmly welcome up to two well-behaved, non-aggressive dogs, although we regretfully cannot accommodate cats

Spring Special: Private Modern Farmhouse, 2hrs NYC

Super private, pet-friendly 13 acre solar powered*, modern farmhouse 2 hours from NYC in Catskills. ✔ Large backyard w/ firepit ✔ Dogs allowed** ✔ 229Mbps wifi ✔ Screen-in porch w/ outdoor dining ✔ 65” Smart TV with Apple TV in living room ✔ 50” Smart TV with Apple TV in guest bed ✔ Bluetooth sound system ✔ Memory foam mattresses ✔ Back deck w/ BBQ grill ✔ Indoor fireplace ✔ Onsite parking 10 mins → Vernooy Falls 20 mins → Minnewaska State Park, Mohonk Preserve & Ashokan Rail Trail

Modern Catskills Cabin with Hot Tub in Accord

Wake to forest views in a modern A-frame with 2 bedrooms, including a cozy loft. Hike nearby trails, soak in the cedar hot tub, or visit local breweries. In summer, barbecue or gather at the fire pit; in winter, warm up by the wood stove on the 2-acre Catskills property. Note: Guests must be 13 or older, and all teenagers must be listed on the reservation. Pets are welcome with prior approval, agreement to pet rules, and payment of the pet fee. Please contact the host before booking.

Fenced & Salt Water Pool | Cozy Catskills Cottage

The perfect spot to unwind with family, friends, and pups. Spend the day hiking, visiting farms, or trying local restaurants, then come home to the yard for kid-and-dog frolicking, “Squirrel TV” through long windows. Soak in the claw-foot tub or the jetted spa tub, then gather by the fire with wine and board games. Swim and make s’mores in summer, watch snow fall in winter, and enjoy peaceful views in every season, relax, play, laugh, repeat.

Willow Treehouse - secluded, unique, romantic

The Willow Treehouse is settled among the trees, overlooking a small, swimmable pond, on a wooded property 15min away from the town of Woodstock. It is cozy, yet has all you need to cook dinner, enjoy reading, sit on the couch and stare outside the window, or swim. No WiFi and no cell service = fully disconnecting from daily life and true relaxation. Perfect for couples and solo adventurers (2 adults max). STR operating permit #21H-109

Cozy Catskill Cabin on Acorn Hill

Enjoy a rustic respite from the city in this cozy cabin on 3.5 acres near the beautiful Ashokan reservoir and Catskill Park. Perfect for a relaxing weekend and as a hub for skiing and hiking. Cabin includes 1 bedroom and one bath, full kitchen, and living room with piano. This is a perfect get-away to relieve the stress of the city. Full amenity details are available in the listing. Town of Olive Registration # STR-22-19

ENTER HOME - Minimalistic style warm & inviting

ENTER our HOME with an inviting comfortable setting filled with natural light and clean lines inspired by Nordic Design. Full new kitchen with all Bosch appliances including washer and dryer. Our home is designed to embrace the beautiful nature around you and to bring peace and comfort to your stay. ENTER HOME is great for individuals, couples, or families with kids. AC in both bedrooms only