Renovated Chalet with Hot Tub and Pond

Roscoe, NY
  • 2 Bedrooms
  • 1 Bathrooms
  • 4 Guests

The Home

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.
As you step through the front doors, you’ll be greeted by a wall of windows on your right, flooding the interior with natural light. The expansive open area seamlessly combines the living room and an inviting eat-in kitchen. The bathroom, adorned with beautiful tile work, is a sight to behold. Sunlight bathes the open floor plan throughout the day, creating an ideal environment for conversations while preparing a meal or enjoying a glass of rosé. Vaulted ceilings add to the spacious and airy ambiance, making this an inviting space...

Home Features


Enjoy the comforts of home and beyond with these distinctive features.

Air Conditioning

Heating

Bathtub

Patio/Balcony

Pets Allowed

Building Elevator

Free Parking

Concierge Services

Waterfront

Pool

Kids Amenities

Hot Tub

All stays include

We believe certain amenities should be standard. Every home comes outfitted with these best-in-class essentials for a worry-free stay.

24/7 Support
Professional Cleaning
High-Speed WiFi
Kitchen Essentials
Starter Kit of Bathroom Amenities
Premium Linens and Towels
Television

For digital free stays

We understand that sometimes you seek a truly unplugged experience. Our Tiny Home rentals may not include amenities like TV or Wi-Fi inside the home. Refer to the listing details for available features.

Home Details


Beds & Bath

Review bedroom arrangements to make sure each is right for you. Full and half bathrooms are shown as one total.

BEDROOM 1
1 King Bed
BEDROOM 2
1 Queen Bed
Bathrooms
1

Attributes

Waterfront


Amenities

Stove

Hair Dryer

Microwave

Fire Extinguisher

Heating

Carbon Monoxide Alarm

First Aid Kit

Hot Tub

Smoke Alarm

Oven

Air Conditioning: Central

Grill: Charcoal

Kids Amenities

Dishwasher


The Neighborhood

The Catskills and Hudson Valley are fantastic destinations for anyone looking to escape the city and experience a blend of natural beauty, vibrant culture, and small-town charm. This region is famous for its rolling mountains, lush forests, and scenic river views—perfect for hiking, biking, kayaking, or simply soaking up the outdoors. In autumn, the foliage is truly spectacular, painting the landscape in vibrant colors. Throughout the area, you’ll discover a unique mix of history and creativity, with beautifully preserved architecture, art galleries, boutique shops, and a thriving farm-to-table dining scene featuring fresh local produce and artisanal goods. Weekend markets, cozy cafés, and a welcoming community vibe are found in every corner. The region is rich in culture, with attractions like Olana, Clermont State Historic Site, and regular art shows, music events, and seasonal festivals. Whether you’re after adventure, relaxation, or a foodie experience, the Catskills and Hudson Valley deliver it all—making any of these charming towns a perfect home base for exploring this special corner of New York. Roscoe, affectionately known as “Trout Town, USA,” is a haven for anglers and outdoor lovers, where the legendary Beaverkill and Willowemoc rivers converge. The town’s unique claim to fame is its world-class fly fishing, drawing visitors from around the globe to its pristine waters and historic fishing lodges. Beyond the rivers, Roscoe offers a classic Catskills experience with rustic inns, local breweries, and a main street lined with gear shops and cozy cafés. The surrounding forests and hills provide endless opportunities for hiking, camping, and wildlife watching. Roscoe’s blend of sporting heritage, natural beauty, and small-town friendliness makes it a must-visit for anyone seeking both adventure and relaxation in the Catskills. Things to See & Do: • Things to Do: - Go fly fishing at Junction Pool or Willowemoc Creek. - Visit the Catskill Fly Fishing Center & Museum. - Enjoy craft beer at Roscoe Beer Company. - Explore the Roscoe O&W Railway Museum. - Picnic or play at Trout Town USA Park. - Attend the annual Trout Parade. - Shop at local outfitters for fishing gear. - Camp or hike in nearby state forests. • Things to See: - The confluence of Beaverkill and Willowemoc at Junction Pool - Catskill Fly Fishing Center & Museum’s riverside campus - Roscoe Diner’s classic neon sign - Willowemoc Creek’s trout-filled waters - Beaverkill Covered Bridge’s historic wooden span (nearby) - Trout Town USA Park’s riverfront setting - Roscoe O&W Railway Museum’s vintage railcars - Rolling hills and farmland surrounding the hamlet • Golf Courses: Roscoe Mountain Club, Villa Roma Resort Golf Course, Twin Village Golf Course • Museums: Catskill Fly Fishing Center & Museum, Roscoe O&W Railway Museum, Time and the Valleys Museum (Grahamsville, nearby) • Local Markets: Roscoe Farmers Market, Livingston Manor Farmers Market (nearby), Callicoon Farmers Market (nearby), Roscoe Beer Company Market • Local Restaurants & Shopping - Restaurants: Roscoe Diner, The Junction, Raimondo’s Restaurant & Pizzeria, Roscoe Beer Co., The Courtyard, Riverside Café, Northern Farmhouse Pasta - Shops: Beaverkill Angler, Roscoe Beer Co. Shop, Catskill Flies, Prohibition Distillery Shop, Junction Pool Gifts, Roscoe General Store, Northern Farmhouse Pasta Shop Annual Festivals & Events: • Roscoe Trout Parade • Roscoe Rockland Chamber of Commerce Fall Festival • Catskill Fly Fishing Center Summerfest • Livingston Manor Trout Parade (Livingston Manor, nearby) • Callicoon Country Fair (Callicoon, nearby) • Roscoe Beer Fest • Roscoe Catskills Pride Festival • Livingston Manor Ice Carnival (Livingston Manor, nearby) • Delaware County Fair (Walton, nearby) • Sullivan County Fair (Liberty, nearby)

Let’s try that again.

We’re having trouble connecting to Google Maps. Please try refreshing your browser or trying your search again.

Things To Know

Check-in4:00PM
Check-out11:00AM

  • Ground Floor

Payment & Cancellation - 30 Day Policy

Grace Period:

  • Guests may cancel for free provided that: (1) reservation is canceled within 48-hours of reservation confirmation, and (2) reservation was confirmed at least 11 days before scheduled arrival.

Payment Policy:

  • 30 days or less prior to arrival: Guests pay 100% at time of reservation.
  • More than 30 days before arrival: Guests pay 50% at time of reservation, the remaining 50% will be charged 30 days prior to arrival.
  • For guests paying with Points or Cash & Points: 100% of payment of both Cash & Points will be deducted at time of reservation, once booking is verified within 48 hours.

Cancellation Policy:

  • 30 days or less prior to arrival: No refund issued, unless ‘Grace Period’ applies.
  • More than 30 days before arrival: 100% refund.

House rules

  • SuitableForChildren,SuitableForInfants,Start: 22:00, End: 8:00
Property ID:D-40507691
    From
    132
    USD/night