Vacation rentals in Callicoon Center, NY with free parking

Escape to this breathtaking 4-bed, 4 bath retreat in Livingston Manor. On a serene 5-acre lot, this modern home offers contemporary living spaces and outstanding outdoor amenities. Enjoy a cedar hot tub, a deck with grill and a backyard oasis with outdoor dining, firepit, hammocks & lawn games. Inside, a cozy fireplace, chef’s kitchen, study & basement with a second TV/games room. Nearby towns Livingston Manor (10 min), Roscoe (10 min) & Callicoon (25 min) Welcome to this stunning 4-bedroom, 4-bathroom home nestled in picturesque Livingston Manor, NY. With its expansive 5-acre lot, this property offers a serene and luxurious retreat for up to 10 guests. As you step into this bright and modern home, you’ll be captivated by the abundance of natural light streaming through large windows, illuminating the sleek finishes and exquisite design elements throughout. Every detail has been carefully considered to provide outstanding amenities and create a space that is both visually stunning and inviting. The inviting covered porch, adorned with rocking chairs, beckons you to relax and soak in the tranquility of the surroundings. Enter through the sweeping front foyer, and you’ll find a sitting room boasting an impressive fireplace, perfect for cozy evenings with loved ones. The heart of this remarkable home is the Chef’s kitchen, a culinary enthusiast’s dream. The clean white tile backsplash creates a pristine backdrop for the sleek black cabinetry, exuding modern sophistication. Equipped with state-of-the-art appliances, including a tortilla press, food processor, blender, Sodastream, paella pan, wok, and pasta machine. Bask in the glow of natural light as you move effortlessly through the kitchen, enjoying picturesque views through the large sliding doors that seamlessly connect indoor and outdoor living. For your entertainment, the adjacent TV room offers a cozy retreat with large windows and a comfortable sectional sofa, perfect for enjoying your favorite shows. In the basement, you’ll discover a second TV/games room where excitement awaits. Engage in friendly competition with the Buck Hunter arcade game and shuffleboard table, or set the mood with the vinyl player and Bluetooth speaker. Unleash your inner rockstar with the karaoke microphones and speaker, creating unforgettable moments of musical fun. Dive into classic board games like Jenga and chess, ensuring endless entertainment for everyone. Venture outside to the wooden deck, where an enchanting outdoor dining area awaits. Gather around the large table and chairs to savor meals al fresco while taking in the beautiful surroundings. Lounge on the sun loungers, soaking up the sun’s rays, or fire up the BBQ grill for outdoor cooking. Descend from the deck to discover a delightful patio adorned with a firepit, creating the perfect ambiance for cozy evenings under the starlit sky. The sleeping accommodations are equally impressive. The large master bedroom on the first level features a queen bed and a luxurious en-suite bathroom with a freestanding bathtub and double vanity, providing a private sanctuary for relaxation. On the second floor, the two guest bedrooms offer a queen bed or two full beds with a shared full bathroom on the same level. The basement level offers a fourth bedroom with a full over full bunk bed and another full bathroom. Additionally, two of the bedrooms are equipped with convenient workstations, should any work needs arise during your stay. AC units exist in the master bedroom and main living space, all other bedrooms have fans. The property shines with outdoor entertaining options, most notably the stunning cedar hot tub. Unwind in the hammocks on the lush lawn, engage in a friendly game of bocce or cornhole, or explore the surrounding area with the provided wiffle ball equipment. Discover the perfect blend of privacy, contemporary design, and limitless entertainment options in this remarkable Livingston Manor retreat. Book your stay now and create unforgettable memories in this idyllic haven. Clancy House is less about 2 hours from New York City, and while you’ll definitely want a car to get there and around the area, there is also a Short Line bus to the city from Monticello, about 25 minutes away. In the winter, we recommend a car with four-wheel drive that can handle the snow and gravel roads. A/C: There is a split unit A/C in the living room and master bedroom. Both upstairs bedrooms are equipped with ceiling fans, and the basement stays naturally cool throughout the year. License number: 10470723

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 Bedrooms, 2 Baths, 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. This home uses door code entry for self-check-in; your door code is sent by email and text within two weeks of arrival. Early check-in and late check-out are available upon request (subject to availability). Please contact us at least 24 hours in advance. • Winter Access Notice: A 4WD or AWD vehicle is strongly recommended to access the home during the snowy season. Guests without the appropriate vehicle may be unable to reach the property. Portoro cannot be held responsible for access issues or assist if a vehicle becomes stuck. 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 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 to 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 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

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. Woodland Chalet, Home Features: • 3 Bedrooms, 2 Baths, 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. This home uses door code entry for self-check-in; your door code is sent by email and text within two weeks of arrival. Early check-in and late check-out are available upon request (subject to availability). Please contact us at least 24 hours in advance. • Winter Access Notice: A 4WD or AWD vehicle is strongly recommended to access the home during the snowy season. Guests without the appropriate vehicle may be unable to reach the property. Portoro cannot be held responsible for access issues or assist if a vehicle becomes stuck. 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 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 to 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 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

Brookside Manor is an elegant country escape in the heart of the Catskills, located 2 hours from NYC. Set on 8 acres with open meadows and babbling brooks, this home has 4 bedrooms and 2 full baths. Amenities include a heated swimming pool, fireplace, firepit, outdoor dining, and access to the best hiking and dining in the region. Livingston Manor and Jeffersonville are both under 10 minutes away. With Brookside Manor’s light-filled rooms, and almost 8 acres of prime, stream-front land, there’s plenty of room to relax and explore. As easy as it is to get lost in the allure of the bucolic setting — an expansive lush, green lawn, with spots of thick moss, a lovely bluestone patio for outdoor dining, a beautiful salt-water pool with a sundeck, a charming campfire circle surrounded by Adirondack chairs, a rolling brook through the entire length of the backyard, ripe apples and pears from mature fruit trees — the house itself really is the main attraction. A semi-circular paved driveway leads behind the house, and passes under a covered portico along the side. The newly renovated kitchen features a custom Sub-Zero refrigerator, a stunning Bertazzoni oven, substantial workspace and beautiful black soapstone counters. Just off the kitchen, through an arched doorway, is a little breakfast nook with windows through which you’ll find yourself birdwatching over coffee, while there’s a large dining room just around the corner featuring a century-old farm table from Spain. Enjoy the views from the calming but cheerful sunroom, a wonderful hang-out spot. A generous stone fireplace anchors the far end of the living room. Original old-growth heart pine woodwork, and aged oak floors have been lovingly cared for over the years, and provide a warm counterpoint to the white stucco walls throughout the house. Along the back hallway you’ll find a large, full bathroom with a bathtub and walk-in shower, as well as a cozy den with an Apple TV and full sized futon available for additional sleeping accommodations. Upstairs is the master bedroom, a queen, next to which is a shared bathroom. A glass shower occupies the center of the bathroom, around which is a luxurious soaking tub and a dressing area. Further down the hall are three more bedrooms: two are full-sized, and the smaller room has a twin bed. All of the house’s closets are lined in cedar. Throughout, the house has a serene feeling, a relaxing but modern tone, punctuated by carefully selected art and furniture pieces. On the property, you will find 10 massive spruce trees and an abundance of apple and pear trees and blackberry bushes. Stone trails throughout the property lead to the brook for easy access. The brook itself is enchanting, and the main reason the owners purchased the property, with large swaths of natural rock formations for sunbathing, wading and simply enjoying the sound of the water, which can be heard throughout the property. Perfectly situated, this property is ideal for exploring nearby country towns, including Livingston Manor, Jeffersonville, Narrowsburg, and Callicoon. Whether you enjoy antiquing, restaurants, hiking or other outdoor activities, there is plenty to do. The delightful farmhouse was built by the Menges family in 1930, when they housed a few guests and ran a small farm to supply fresh vegetables, fruit and dairy to the resort they owned at the top of the hill in Shandelee. Brookside Manor is less than two hours from New York City, and while you’ll definitely want a car to get there and around the area, there is also a Short Line bus to the city from Monticello, about 20 minutes away. In the winter, we recommend a car with four-wheel drive that can handle the snow and gravel roads. Note: This home is not equipped with air conditioning. Fans are provided in each bedroom for your comfort. *Please note the pool opens from mid-to-late May until mid-to-late September. Please inquire regarding specific opening and closing dates. License number: 07180919

Welcome to Winterberry Pond, our completely converted barn 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. Spend your evenings soaking under the stars, then gather around the fire pit for s’mores and stories. 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, perfect for easy conversation while preparing a meal or enjoying a glass of rosé. Vaulted ceilings add to the spacious, airy feel, and sunlight pours into the open floor plan throughout the day. The bathroom features beautiful tile work and a walk-in shower. This home comfortably accommodates 4 guests with 2 spacious bedrooms featuring luxury linens. Outside, the home is thoughtfully set back from the road, offering a sense of seclusion and privacy on over 7 acres of Catskills land dotted with mature trees just waiting to be explored. The generously sized yard invites outdoor fun and laid-back evenings, with an upgraded hot tub area that’s ideal for soaking under the sky after a day of hiking or skiing. Gather around the fire pit for s’mores and stories, then wind down with the quiet of the woods all around you. Spend summer afternoons row boating on the private pond and keep an eye out for local wildlife. Please note: while you’re welcome to enjoy the pond, we would not recommend swimming in it. The pond is intended for canoeing and fishing only. 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. • Upgraded hot tub area for relaxing and taking in the views. • 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: while you’re welcome to enjoy the pond, we would not recommend swimming in it. The pond is intended for canoeing and fishing only. • Convenient proximity to hiking trails, nature, and ski mountains for year-round outdoor activities. • Short drive to the towns of Roscoe and Livingston Manor. • The internet at this property is provided by Starlink. While speeds are typically strong, service can occasionally fluctuate due to weather and other factors and may not always allow a perfectly consistent connection. • Winter Access Notice: The driveway and parking area is plowed in winter. During snowy conditions, a 4WD or AWD vehicle is strongly recommended for reaching the home. If you’re traveling without one, access may be difficult or not possible at times. Portoro cannot be held responsible for weather-related access issues or provide assistance if a vehicle becomes stuck. Portoro offers convenient self check-in. Check-in instructions will be sent by email and text prior to arrival with everything you need to access the home easily and on your schedule. You’ll also receive a digital Guest Guide for the home, packed with helpful tips, house info, and local recommendations to make the most of your stay. • 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. • Winter Access Notice: A 4WD or AWD vehicle is strongly recommended to access the home during the snowy season. Guests without the appropriate vehicle may be unable to reach the property. Portoro cannot be held responsible for access issues or assist if a vehicle becomes stuck. 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) House Rules & Important Information By booking with Portoro, guests agree to the guidelines below to help ensure a safe, respectful, and enjoyable stay. • Portoro Rental Agreement + Identity Registration, All guests staying at a Portoro property are required to complete identity registration and sign a rental agreement via e-signature. • Age Requirement, The reservation holder must be 25+. • Arrival Support + House Manual + 24/7 Support, Upon arrival, Portoro aims to ensure your safety, proper access to the home, and understanding of guest features. All guests are required to read the house manual upon arrival. If you have any questions, please reach out to Portoro; our team is available 24/7. • Directions + Check-In Details, Before check-in, Portoro will send all check-in details, detailed directions, and a digital guest guide for the home by email and text to help ensure a seamless arrival. • Check-In / Check-Out (Early/Late Requests), Check-in is 4:00pm and check-out is 11:00am. We can’t guarantee early check-ins or late check-outs, and a fee typically applies. When approved, fees apply for times outside a one-hour window of standard check-in/check-out. If you need significant flexibility, the best option is to book an additional night. • Local Taxes (Including Extended Stays), In New York State and Greene County, hotel/vacation rental hosts are required to collect hotel tax, which Portoro collects within the booking transaction. For stays over 29 days, please inquire with Portoro regarding terms and conditions and any applicable tax exemptions. • Animals/Pets, No Pets: This is a no pets property. A $150/day fee will apply for violations, and you may be asked to vacate the premises with no refund (at the discretion of Portoro). Portoro follows ADA guidelines, and any additional community or HOA rules may apply. • No Smoking, This is a no smoking property. Penalty fees apply for violations, and you may be asked to vacate the premises with no refund at the discretion of Portoro. • No Parties or Events, Parties and events are not permitted. • Quiet Hours, 10:00pm–8:00am. These hours reflect local residential and regional expectations; please keep noise low and be mindful of neighbors. • Report Damages, Any known damages incurred during your stay must be reported to the property manager immediately. • Security, Some Portoro properties have exterior-only cameras for monitoring. • Local or Property Water Features, Some Portoro properties may have pools, hot tubs, or other nearby water features. There is no guard around water features; use at your own risk. • Wildlife + Pests, You will likely see wildlife during your stay (deer, turkeys, groundhogs, foxes, etc.). Please note: We are in bear country, so it’s very important to discard all garbage in the secure bear-proof bin (warmer months) or garbage can (winter). For homes that include/offer BBQs, all food items should be brought inside and BBQs scraped clean after use to avoid attracting wildlife. The home is regularly treated for pests, but because we’re in the country, it’s not unusual for an occasional insect or mouse to make an appearance. • Private pond on the property for row boating and various activities. Please note: while you’re welcome to enjoy the pond, we would not recommend swimming in it. The pond is intended for canoeing and fishing only. • 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. License number: STR48-23

Escape to Hemlock Hill Barn, a beautifully constructed barn with 3-bedrooms and 1.5 bathroom - just 2.5 hours from NYC! Within this stunning barn, discover a tranquil countryside oasis with upscale rustic charm and outdoor enjoyment. Inside, find perfectly curated, cozy spaces and a warm wood stove. Outside, enjoy a hot tub, outdoor dining with BBQ, a firepit & pond. Nearby towns like Callicoon (8 mins), (Jeffersonville (15 mins) and Narrowsburg (25 mins) offer dining and shopping delights. Located on a tranquil back road in the Beechwoods, above Callicoon, Hemlock Hill Barn is a beautifully constructed barn on a sprawling 14.45-acre lot offering a unique blend of authentic country charm and rustic allure in a secluded setting. Stepping onto the property, you’re immediately embraced by its tranquility and stunning views of the rolling western hills. Outdoor lovers will find plenty to enjoy with amenities including a peaceful pond and a cozy firepit ideal for gathering under the stars. Step inside to discover a haven of warmth and character. The ground floor welcomes you with a slate entry leading to the first bedroom with a king bed, large TV, and French doors opening onto a picturesque bluestone patio with the hot tub and built-in barbecue. Enjoy summer dining and entertaining while overlooking the serene pond just beyond. A second downstairs bedroom offers a queen bed and doors that open directly onto the deck. Ascend to the open first floor where the great room awaits with plush couches and a warm woodstove, perfect for cozy evenings inside. A dining area and kitchen beckon with their blend of rustic elegance and modern convenience, featuring double farm sinks, bluestone and butcher-block counters, a commercial propane stove, and top-of-the-line appliances. Every window frames breathtaking views of the rolling hills and lush greenery. Venture up to the lofted second floor where another king bed awaits, offering a peaceful retreat at the end of the day. Escape the hustle and bustle of everyday life and immerse yourself in the genuine charm of country living at Hemlock Hill Barn. This idyllic property offers the perfect blend of rustic charm and modern comforts for your next getaway! Please note: There are NO blinds/curtains in the bedrooms. Hemlock Hill Barn is just about 2.5 hrs hours from New York City and guests can travel around by car as it is a rural area with limited public transportation. In the winter, we recommend a car with four-wheel drive that can handle the snow and gravel roads. ** NOTE: The house does not have air conditioning. Fans are available for the bedrooms.

<b>Redesigned and renovated in May 2025, The Gables</b> is a charming 8-bedroom, 2.5-bath farmhouse in the heart of Callicoon, a scenic riverfront town in the Catskills just 2.5 hours from NYC. Set on a half acre and within walking distance to restaurants and shops, the home features cozy amenities like a wood-burning stove, outdoor dining, and easy access to the area’s best hiking and dining. Perfect for groups, The Gables offers charm, comfort, and convenience in a central location. Set on a pretty property on the edges of the popular river hamlet of Callicoon, The Gables is a rare gem among large in-town homes, boasting light-filled spaces and designer finishes. Its backyard oasis leads down to a year-round stream, and it is a great option for guests looking for a relaxing country house while not being in an isolated location. This dramatic three-story getaway has an open, airy vibe, with white walls and wood floors enhanced by vibrant pops of color. The first floor features an open-plan living and dining area, where a roaring fire can be enjoyed in the living room’s wood stove. Chefs won’t miss a moment of the conversation thanks to the kitchen’s bluestone-countered passthrough, which keeps everyone connected. The spacious kitchen, outfitted with butcher block counters, leads out to a newly installed multi-level wood deck, stained black for a striking finish. Just beyond, a path of bluestone steps winds down to a substantial wooden meditation/yoga platform, thoughtfully positioned to soak in the soothing sounds of the nearby stream. Back inside, the main floor includes a comfortable queen bedroom with easy access to the living areas and a shared half bath just across the hall. The playroom at the front of the hallway is ideal for a movie night and/or space for the little ones to spread out. The second floor mirrors the open, airy layout of the first. Rooms on either side of the stairwell have been reimagined to create two expansive bedroom suites, each with its own lounge area. The primary suite is accessed through a private sitting room and flows into what was once a spacious dressing room—now transformed into a cozy lounge with a daybed. Across the hall, a second large suite features a queen bed and generous space to relax. At the end of the hall, you’ll find a shared bathroom with a tub/shower combo and a separate water closet. A third bedroom on this floor offers a single bed, perfect for a child or solo guest. The original layout was left intact on the third floor in the form of four medium-sized bedrooms. The first guest room has an L-shaped layout with a King bed on one end and a full bed in the alcove around the corner. There are three other guest rooms off the hallway, along with a shared bathroom with a clawfoot tub with hand-held shower. The Gables is just a few minutes’ walk down to the main streets of Callicoon, with its restaurants, movie theater and local brewery, as well as easy access to the Delaware River with arguably some of the best fly fishing in the region. There are also very good cycling and hiking opportunities along the Delaware River. The Gables is just over two hours from New York City, and you’ll definitely want a car to get there and to explore around the area. A/C: Window units are available during summer months for 5 out of the 7 bedrooms License number: 06400318

On a quiet road in peaceful Callicoon, this three-story farmhouse is a welcoming retreat. Picture windows offer bucolic views with cozy seating. The dining room seats 6 and has easy access to the kitchen or patio. A full bath rounds out the 1-Fl. Two bedrooms on the 2-Fl, both queen-sized beds share a bathroom with a walk-in shower. The 3-Fl has two twin rooms and a queen and shares a bath with a clawfoot tub. Enjoy sweeping lawns, a bluestone patio with a gas grill, dining, and cafe lights. Your escape begins down a quiet, dead end road as you approach the picturesque solitude of Five Acres Farm. Nestled in the sleepy Beechwoods area of Callicoon, this expansive three-story farmhouse is a welcoming retreat. Spacious is an understatement at Five Acres Farm. Picture windows throughout the living room both illuminate the space and offer up bucolic view from the comfortable seating. Tucked into an alcove, there is also a cozy sectional to cuddle up on while watching your favorite movie. Across the entryway you’ll find the dining room with seating for six and easy access to the kitchen or patio. This open layout makes indoor or outdoor dining a breeze. A full bathroom between living and dining areas rounds out the first floor. Upstairs the two bedrooms on the second floor, both with queen-sized beds, are suites. French doors open up to a small home office in one of these primary suites while the other provides a chaise lounge and vanity seating. They share a bathroom with walk-in shower. Continuing up to the third floor are two twin rooms and one queen. The third floor bathroom has a skylight above its deep clawfoot tub and appealing views out to the surrounding woodlands. Lose yourself out on the sweeping lawns. The bluestone patio is equipped with a gas grill and dining arrangement, and cafe lights strung overhead create a magical atmosphere for gathering together at the end of the day. Take your night cap out to the fire pit in the middle of an open field while basking in uninterrupted views of the night sky. The moments created at Five Acres Farm are sure to last longer than your stay. Hop in the car and enjoy driving the scenic, quiet roads of Callicoon. Parking is along the long driveway leading up to the house, please don’t park on the grass. ** NOTE: The house does not have air conditioning. Fans are available for the bedrooms. License number: 09190522