Roscoe, New York
Renovated Chalet with Hot Tub and Pond
4.9 • 49 reviews
House
2 bedrooms
2 beds
1 bath
4 guests
Summary
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.
Space
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 for all your gatherings. This home comfortably accommodates 4 guests with 2 spacious bedrooms featuring luxury linens.
Outside, the home is thoughtfully situated away from the road, offering a sense of seclusion and privacy. The property boasts over 7 acres of land, adorned with mature trees that are just waiting to be explored. The generously sized yard provides ample space for outdoor activities, with the additional the included hot tub to relax & soak up the suds & views! Many a summer afternoon can be enjoyed row boating on the private pond, where the abundant wildlife promises to excite and entertain. Please note that while you are welcome to enjoy the pond, we advise using it with extreme caution as it is swim at your own risk.
Sleeping arrangements:
Bedroom 1: 1 king bed
Bedroom 2: 1 queen bed
- Set off the road on 7+ acres of remote Catskills land.
- Cozy living area with open floor plan for convenient entertaining.
- Fully-stocked kitchen with modern appliances and an island with a breakfast bar.
- Modern renovated bathroom featuring a walk in shower.
- 2 spacious bedrooms with luxury linens.
- Spacious backyard for gathering and entertaining including a fire pit, outdoor dining and grill set-up.
- Private pond on the property for row boating and various activities. Please note that while you are welcome to enjoy the pond, we advise using it with extreme caution as it is swim at your own risk,.
- Convenient proximity to hiking trails, nature, and ski mountains for year-round outdoor activities
- Short drive to the towns of Roscoe and Livingston Manor
- INTERNET: The internet at this property is provided by ViaSat a satellite internet company. This can cause the internet to fluctuate and possibly not allow consistent connection.
Guest Access
We offer convenient door codes for self-check-in. Portoro Homes uses convenient keyless entry for self check-in, details provided 2 weeks (or less) prior to arrival by email and text message.
• Early check-ins or late check-outs: If the property happens to be ready earlier than the standard 4 pm check-in time on the day of your arrival, in most cases an early arrival option may be available when confirmed with the main office. Late check-outs must be confirmed with main office staff prior to the date of departure.
The driveway and parking area is plowed in winter, but a four-wheel drive is recommended to explore the area. There is a pond at the property but to please note that while you are welcome to enjoy the pond, we advise using it with extreme caution as it is swim at your own risk.
Getting Around
Getting around Roscoe is part of the adventure—quiet roads follow trout streams and wind through wooded hills, making each drive peaceful and picturesque. With a car, you can easily reach fishing spots, breweries, and neighboring towns, with minimal traffic and plenty of places to stop.
Route 17 provides quick access to other Catskills destinations, while local byways lead to scenic overlooks and the heart of “Trout Town, USA.” Every drive offers a chance to spot wildlife, cross a covered bridge, or discover a new picnic spot by the river.
Cell service is generally reliable in town, but can fade in remote areas, so download maps ahead of time. Parking is easy and free, and the relaxed pace means you can truly enjoy the journey as much as the destination.
Airports:
• Stewart International Airport (SWF): 1 hour 40 minutes
• Albany International Airport (ALB): 2 hours
• New York City Airports (JFK/LGA/EWR): 2.5–3 hours
• Wilkes-Barre/Scranton International Airport (AVP), PA: 1 hour 45 minutes
Popular Landmarks:
• Roscoe Diner (classic eatery)
• Junction Pool (famous fly-fishing spot)
• Catskill Fly Fishing Center & Museum (nearby)
• Trout Town USA Park (recreation)
• Roscoe O&W Railway Museum (railroad history)
• Roscoe Beer Company (brewery)
• Beaverkill Covered Bridge (historic, nearby)
• Willowemoc Creek (fishing, nature)
• Roscoe Campsite Park (camping, events)
• Catskill Scenic Trail (biking/hiking, nearby)
• Trout Parade (annual event)
Other Things to Note
Please pay close attention to following the house rules. Non compliance could result in sizable fines.
- All guests staying at a Portoro Homes are required to sign (esignature) a rental agreement and complete identity registration.
- Age restrictions apply. Reservation holder must be 25 years of age.
- No Parties or Events. - Quiet Hours observed, 10:00pm - 8:00am.
- Upon arrival, we aim to ensure your safety, proper access to the home, and guest features. Should you have any questions, please don't hesitate to reach out to Portoro Homes directly.
- Known damages incurred during your stay must be reported to the property manager immediately.
- Before check in, we will send you detailed directions to ensure a seamless arrival.
- Check-in time is 4:00 p.m. Check-out time is 11:00 a.m.
- We cannot guarantee early check ins or late checkouts, fee typically applies. When it is possible to check in early or check out late, there will be a fee for anything outside of a one hour window within our standard times. If your need for an early check in or late check out is great, your best option is to book an additional night.
- Some homes have cameras for external monitoring only.
- Some homes have pools and hot tubs. There is no guard around the water features. - Use at your own risk.
- The house is regularly treated for pests but being that we are in the country, it would not be unusual to have an insect or mouse make an appearance inside.
- In the State of New York, and in Sullivan County, all hotel and vacation rental hosts are required to collect hotel tax. We collect these taxes within the booking transaction.
- This is a No Pets property. A daily rate fee of $150.00 will apply for violations and you may be asked to vacate the premises with no refund at the discretion of the Host.
- This is a No Smoking property. Penalty fees for violations will apply and you may be asked to vacate the premises with no refund at the discretion of the Host.
- Private pond on the property for row boating and various activities. Please note that while you are welcome to enjoy the pond, we advise using it with extreme caution as it is swim at your own risk,.
- INTERNET: The internet at this property is provided by ViaSat a satellite internet company. This can cause the internet to fluctuate and possibly not allow consistent connection.
Amenities
Air conditioning
BBQ grill
Garden or backyard
Hot tub
Water View
Waterfront
Hair dryer
Hot water
Towels provided
Bed linens
Essentials
27 more
Accommodation
Bedroom 1
1 king bed
Bedroom 2
1 queen bed
Terms & Rules
Quiet hours required between 10:00 PM and 8:00 AM
Pets are not allowed
Suitable for Children
Suitable for Infants
Availability
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Check-in: After 4pm • Check-out: Before 11am
Reviews
4.9 • 49 reviews
C
Chris
May 2025
The house and property were so nice. The views sitting at the pond are amazing. The value is great for a quick getaway.
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B
Brenna
May 2025
The unit was as advertised. Peaceful, clean, private. Easy to check in and out.
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F
Fred
April 2025
Easy to check in, great communication, well appointed with supplies, cookware and amenities.
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A
Anthony
April 2025
Quiet, wonderful property
Great stay, was clean, as advertised. Communication with property owner was easy. Very modern, cozy place to stay.
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Location
Roscoe, New York. Exact location is provided after booking is confirmed.
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)
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