3 Br Private Vacation Home Vacation Rental In Roscoe, New York

Summary:

Experience the best of the Catskills at Woodland Chalet—a spacious, beautifully renovated retreat with 3 bedrooms and multiple outdoor entertainment areas including a fire pit, gazebo, and expansive deck. Perfect for families or groups, you’ll enjoy privacy, comfort, and quick access to Roscoe and Livingston Manor’s top breweries, shops, and fishing.
Please SEE: Other things to note

For Area Details, Please SEE: The neighborhood & Getting around

*Pet Friendly, fee applies per pet.
The Space:

Woodland Chalet, Home Features:

• 3 Bedroom, 2 Bath – Available for up to 6 Guests!

• Expansive Deck With Grill & Outdoor Dining

• Fire Pit & Gazebo In Scenic Wooded Setting

• Beautiful Open Interior, Fireplace, Vaulted Ceilings & Modern Kitchen

• 2 Separate Work From Home Spaces

• 3rd Bedroom Offers Private Entry Foyer/Flex Space With Weight Set

• Free WiFi & Smart TV
NOTE: Hosting a smaller group? Our 2-bedroom chalet listing is ideal for up to 4 guests and is offered at a lower rate.
Nestled on six acres of tranquil Catskills forest, Woodland Chalet is designed for relaxation and connection with nature. The striking A-frame architecture is surrounded by trees, with large windows and an exterior deck that blend indoor and outdoor living. Step outside to a grassy lawn with bright red Adirondack chairs, a short path to a charming gazebo, and a spacious upper deck at the back of the home—elevated above the grounds and perfect for outdoor dining, grilling, and gathering under the stars. The upper deck is accessed directly from inside, while a lower deck and a dedicated fire pit area with modern seating provide even more places to unwind.
This tranquil, renovated abode is only a short distance from two of the hottest towns in the Catskills—Roscoe and Livingston Manor—where you’ll find local breweries, distilleries, shops, art galleries, and some of the best fishing! Enjoy high-speed WiFi, luxury furnishings, thoughtful amenities, and Smart TV in this quiet, picturesque retreat from the city.
Inside, the open-concept great room features vaulted ceilings, a fireplace, and a comfy sectional sofa. The dining area is surrounded by windows and opens to the deck, making it easy to enjoy meals with a view. The kitchen is equipped with modern stainless-steel appliances, open shelving, and all the essentials for cooking and entertaining. On the main level, you’ll also find a full bathroom and a laundry room for convenience.
Bedroom 1 is located on the main level and features a queen bed with a stylish green accent wall. Upstairs, Bedroom 2 is the primary suite with a king bed, ensuite bath, and peaceful woodland views. Both beds are fitted with quality Casper mattresses for cool, comfortable sleep. Just outside the primary bedroom, a loft workspace with a desk and chair is perfect for remote work or creative projects. In the full chalet, the finished basement offers an additional queen bedroom with quality bedding—a flexible space with a weight set and bench area, perfect for morning workouts is offered at the base of the stairs outside of the bedroom.
Whether you’re savoring your morning coffee on the deck, strolling the wooded grounds, or gathering friends and family for a meal outdoors, Woodland Chalet is all about making the most of the Catskills setting. Multiple outdoor entertainment areas invite you to relax and connect: enjoy an expansive deck with an outdoor grill and dining space overlooking the trees, or spend your evenings around the fire pit under the stars. The gazebo is a peaceful spot to pause and take in the woodland views*. Here, every day brings new ways to enjoy the fresh mountain air and the beauty of nature, making this chalet the ideal home base for your Catskills adventure.
Please Note: A 4WD vehicle is required to access the property during the winter months.
*The gazebo does typically offer outdoor seating, which is currently in storage and the gazebo will be furnished after the homeowner has had it re-stained Spring '26.
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.
• We cannot guarantee early check-ins or late check-outs, as both are subject to availability. Please contact us 24 hours prior to check-in to submit your request.
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)
Interaction with Guests:

Our goal is that your vacation exceed your expectations. Portoro Homes communicates via email and phone. After a booking is confirmed, rental agreement will be emailed to the guest for e-signature. Check-in instructions are sent by email and text message 14 days (or less) prior to arrival date. We offer convenient keyless entry for self-check in. We do typically check in with guests by text 1-2 times during their stays to ensure a 5-star experience and remain available for any questions. We are available to guests 24/7 for any inquiries.
• We cannot guarantee early check-ins or late check-outs, as both are subject to availability. Please contact us 24 hours prior to check-in to submit your request.

Located in Roscoe, this vacation home is in a rural area and in the mountains. Villa Roma Driving Range and Sullivan County Golf and Country Club are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Catskill State Park and Willowemoc Wild Forest. Fishing offers a great chance to get out on the surrounding water, or you can seek out an adventure with cycling nearby.