Experience the best of the Catskills at Woodland Chalet—a spacious, beautifully renovated retreat with 2 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.
Woodland Chalet, Home Features:
• 2 Bedroom, 2 Bath – Available for up to 4 Guests!
• Expansive Deck With Grill & Outdoor Dining
• Fire Pit & Gazebo In Scenic Wooded Setting
• Beautiful Open Interior, Fireplace, Vaulted Ceilings & Modern Kitchen
• Cozy Loft Desk for Easy Remote Work
• Free WiFi & Smart TV
NOTE: Need more room? Our 3-bedroom chalet listing accommodates up to 6 guests for larger parties and is available with an additional nightly rate.
Nestled on six acres of tranquil Catskills forest, Woodland Chalet offers a peaceful retreat for relaxation and nature. The home’s striking A-frame architecture is set among towering trees, with large windows and an exterior deck that blend indoor and outdoor living. Enjoy 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 offer 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, so you can enjoy meals with a view. The kitchen is equipped with modern stainless-steel appliances, open shelving, and everything you need for cooking and entertaining. The main level also includes 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.
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.
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 Portoro Homes. Late check-outs must be confirmed with Portoro Homes prior to the date of departure.
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)
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.
- A 4WD vehicle is required to access the property during the winter months.
- 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. 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.
- 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 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.
- Animals/Pets -- Dogs Only, Guidelines and Fee*
Animals/pets must be disclosed prior to reservation arrival date, maximum of 2 per stay, dogs only. A $150.00 fee per animal/pet is required. Animals/pets are not permitted anywhere on the premises unless prior approval is obtained. Any unauthorized animals/pets at the property will result in a $150.00 per day / per animal/pet fee, and may result in your reservation being canceled, and you may be required to vacate from the Property.
License number: STR6-24