Home Vacation Home Rentals By Owner In Roscoe, NY

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Exceptional(27)

$749.19

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Private Vacation Home

Amber Acres Lodge; Spacious Log Cabin with Mountain Views and Lake Access

Roscoe, New York, United States

Large 4-bedroom log cabin that exudes coziness from the inside out. Set on a gorgeous, 15+ acre property and only 7 minutes from both downtown Livingston Manor and Roscoe. Stay home and enjoy the mountainous views, watch for wildlife, or head into the nearby towns for an amazing food, brewery or vintage shopping scene!brbrOur log home merges the essence of the Catskill mountains with the textures and minimalistic design of a Scandinavian cottage. Our aesthetic is warm, simple, and luxurious. We feature local art, vintage pieces, and a touch of boucle wherever possible.brbrWell-equipped, well-stocked kitchen with mountain views and 4 bar stools.brHandmade, wooden table that comfortably seats 6 or more.brOutdoor dining room with log table and 4 seats, plus bar stools for additional guests.brbrComfortable living room with 2 couches, a swivel loveseat, and additional nook seating. Wood burning fireplace for cuddling up, plus thermostats in every room for ease of use. And in the warmer months, fans throughout. Open layout indulges an entertainer's dream.brbrAnd when the weather is right, enjoy our deck and vast 15 acre property. We've got no shortage of Adirondack chairs, picnic tables and more.brbrLAYOUTbrbrFirst floor:br- Enter in accommodating mudroom or through the garagebr- Half bathroom in entryway hallwaybr- Open layout kitchen, dining room and living roombr- Play room with futonbr- Primary bedroom with full bathroombr- Furnished deck with grill; accessible from living room, master bedroom and via stairs from the outsidebrbrSecond floor:br- Open loft area with queen bed nooked into windowbr- Upstairs bedroom 1 with queen bed and futonbr- Upstairs bedroom 2 with queen bedbr- Upstairs full bathroombrbrBasement coming soon!
Bed 5

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Bath 3

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Sleep 8

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Exceptional(6)

$262.18

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Private Vacation Home

Hot Tub, Private Pond, Fire pit

Roscoe, New York, United States

Summary:brbrWelcome 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.brbrbrbrThe Space:brbrAs 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.brbrbrbrOutside, 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.brbrbrbrSleeping arrangements:brbrBedroom 1: 1 king bedbrbrBedroom 2: 1 queen bedbrbrbrbr- Set off the road on 7+ acres of remote Catskills land.brbr- Cozy living area with open floor plan for convenient entertaining.brbr- Fully-stocked kitchen with modern appliances and an island with a breakfast bar.brbr- Modern renovated bathroom featuring a walk in shower.brbr- 2 spacious bedrooms with luxury linens.brbr- Upgraded hot tub area for relaxing and taking in the viewsbrbr- Spacious backyard for gathering and entertaining including a fire pit, outdoor dining and grill set-upbrbr- 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.brbr- Convenient proximity to hiking trails, nature, and ski mountains for year-round outdoor activitiesbrbr- Short drive to the towns of Roscoe and Livingston Manorbrbrbrbr• 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.brbr• 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 Homes cannot be held responsible for weather-related access issues or provide assistance if a vehicle becomes stuck.brbrbrbrGuest Access:brbrPortoro Homes 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.brbrbrbr• Early check-ins or late check-outs: Standard check-in time is 4:00 p.m. and standard check-out time is 11:00 a.m. If the home is ready earlier on the day of arrival, an early check-in may be available when confirmed with our main office. Late check-outs must be requested and confirmed by our main office prior to departure.brbrbrbrThe Neighborhood:brbrThe 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.brbrbrbrRoscoe, 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.brbrbrbrThings to See & Do:brbr• Things to Do: brbr- Go fly fishing at Junction Pool or Willowemoc Creek.brbr- Visit the Catskill Fly Fishing Center & Museum.brbr- Enjoy craft beer at Roscoe Beer Company.brbr- Explore the Roscoe O&W Railway Museum.brbr- Picnic or play at Trout Town USA Park.brbr- Attend the annual Trout Parade.brbr- Shop at local outfitters for fishing gear.brbr- Camp or hike in nearby state forests.brbrbrbr• Things to See: brbr- The confluence of Beaverkill and Willowemoc at Junction Poolbrbr- Catskill Fly Fishing Center & Museum’s riverside campusbrbr- Roscoe Diner’s classic neon signbrbr- Willowemoc Creek’s trout-filled watersbrbr- Beaverkill Covered Bridge’s historic wooden span (nearby)brbr- Trout Town USA Park’s riverfront settingbrbr- Roscoe O&W Railway Museum’s vintage railcarsbrbr- Rolling hills and farmland surrounding the hamletbrbrbrbr• Golf Courses: Roscoe Mountain Club, Villa Roma Resort Golf Course, Twin Village Golf Coursebrbrbrbr• Museums: Catskill Fly Fishing Center & Museum, Roscoe O&W Railway Museum, Time and the Valleys Museum (Grahamsville, nearby)brbrbrbr• Local Markets: Roscoe Farmers Market, Livingston Manor Farmers Market (nearby), Callicoon Farmers Market (nearby), Roscoe Beer Company Marketbrbrbrbr• Local Restaurants & Shoppingbrbr- Restaurants: Roscoe Diner, The Junction, Raimondo’s Restaurant & Pizzeria, Roscoe Beer Co., The Courtyard, Riverside Café, Northern Farmhouse Pastabrbr- Shops: Beaverkill Angler, Roscoe Beer Co. Shop, Catskill Flies, Prohibition Distillery Shop, Junction Pool Gifts, Roscoe General Store, Northern Farmhouse Pasta ShopbrbrbrbrAnnual Festivals & Events:brbr• Roscoe Trout Paradebrbr• Roscoe Rockland Chamber of Commerce Fall Festivalbrbr• Catskill Fly Fishing Center Summerfestbrbr• Livingston Manor Trout Parade (Livingston Manor, nearby)brbr• Callicoon Country Fair (Callicoon, nearby)brbr• Roscoe Beer Festbrbr• Roscoe Catskills Pride Festivalbrbr• Livingston Manor Ice Carnival (Livingston Manor, nearby)brbr• Delaware County Fair (Walton, nearby)brbr• Sullivan County Fair (Liberty, nearby)brbrbrbrGetting Around:brbr- 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.brbrbrbrGetting 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.brbrbrbrRoute 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.brbrbrbrCell 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.brbrbrbrAirports:brbr• Stewart International Airport (SWF): 1 hour 40 minutesbrbr• Albany International Airport (ALB): 2 hoursbrbr• New York City Airports (JFK/LGA/EWR): 2.5–3 hoursbrbr• Wilkes-Barre/Scranton International Airport (AVP), PA: 1 hour 45 minutesbrbrbrbrPopular Landmarks:brbr• Roscoe Diner (classic eatery)brbr• Junction Pool (famous fly-fishing spot)brbr• Catskill Fly Fishing Center & Museum (nearby)brbr• Trout Town USA Park (recreation)brbr• Roscoe O&W Railway Museum (railroad history)brbr• Roscoe Beer Company (brewery)brbr• Beaverkill Covered Bridge (historic, nearby)brbr• Willowemoc Creek (fishing, nature)brbr• Roscoe Campsite Park (camping, events)brbr• Catskill Scenic Trail (biking/hiking, nearby)brbr• Trout Parade (annual event)
Bed 2

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Bath 1

Bath

Sleep 4

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Exceptional(2)

$308.62

/ Nightly
Private Vacation Home

2BR Chalet: Deck, Fireplace, Loft, Forest Views

Roscoe, New York, United States

Summary:brbrExperience 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.brbrbrbrPlease SEE: Other things to notebrbrFor Area Details, Please SEE: The neighborhood & Getting aroundbrbr*Pet Friendly, fee applies per pet.brbrbrbrThe Space:brbrWoodland Chalet, Home Features:brbr• 2 Bedroom, 2 Bath – Available for up to 4 Guests!brbr• Expansive Deck With Grill & Outdoor Diningbrbr• Fire Pit & Gazebo In Scenic Wooded Settingbrbr• Beautiful Open Interior, Fireplace, Vaulted Ceilings & Modern Kitchenbrbr• Cozy Loft Desk for Easy Remote Workbrbr• Free WiFi & Smart TVbrbrbrbrNOTE: Need more room Our 3-bedroom chalet listing accommodates up to 6 guests for larger parties and is available with an additional nightly rate.brbrbrbrNestled 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.brbrbrbrThis 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.brbrbrbrInside, 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.brbrbrbrBedroom 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.brbrbrbrWhether 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.brbrbrbrPlease Note: A 4WD vehicle is required to access the property during the winter months.brbrbrbr*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.brbrbrbrGuest Access:brbrWe 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.brbrbrbr• 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.brbrbrbrThe Neighborhood:brbrThe 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.brbrbrbrRoscoe, 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.brbrbrbrThings to See & Do:brbr• Things to Do: brbr- Go fly fishing at Junction Pool or Willowemoc Creek.brbr- Visit the Catskill Fly Fishing Center & Museum.brbr- Enjoy craft beer at Roscoe Beer Company.brbr- Explore the Roscoe O&W Railway Museum.brbr- Picnic or play at Trout Town USA Park.brbr- Attend the annual Trout Parade.brbr- Shop at local outfitters for fishing gear.brbr- Camp or hike in nearby state forests.brbrbrbr• Things to See: brbr- The confluence of Beaverkill and Willowemoc at Junction Poolbrbr- Catskill Fly Fishing Center & Museum’s riverside campusbrbr- Roscoe Diner’s classic neon signbrbr- Willowemoc Creek’s trout-filled watersbrbr- Beaverkill Covered Bridge’s historic wooden span (nearby)brbr- Trout Town USA Park’s riverfront settingbrbr- Roscoe O&W Railway Museum’s vintage railcarsbrbr- Rolling hills and farmland surrounding the hamletbrbrbrbr• Golf Courses: Roscoe Mountain Club, Villa Roma Resort Golf Course, Twin Village Golf Coursebrbrbrbr• Museums: Catskill Fly Fishing Center & Museum, Roscoe O&W Railway Museum, Time and the Valleys Museum (Grahamsville, nearby)brbrbrbr• Local Markets: Roscoe Farmers Market, Livingston Manor Farmers Market (nearby), Callicoon Farmers Market (nearby), Roscoe Beer Company Marketbrbrbrbr• Local Restaurants & Shoppingbrbr- Restaurants: Roscoe Diner, The Junction, Raimondo’s Restaurant & Pizzeria, Roscoe Beer Co., The Courtyard, Riverside Café, Northern Farmhouse Pastabrbr- Shops: Beaverkill Angler, Roscoe Beer Co. Shop, Catskill Flies, Prohibition Distillery Shop, Junction Pool Gifts, Roscoe General Store, Northern Farmhouse Pasta ShopbrbrbrbrAnnual Festivals & Events:brbr• Roscoe Trout Paradebrbr• Roscoe Rockland Chamber of Commerce Fall Festivalbrbr• Catskill Fly Fishing Center Summerfestbrbr• Livingston Manor Trout Parade (Livingston Manor, nearby)brbr• Callicoon Country Fair (Callicoon, nearby)brbr• Roscoe Beer Festbrbr• Roscoe Catskills Pride Festivalbrbr• Livingston Manor Ice Carnival (Livingston Manor, nearby)brbr• Delaware County Fair (Walton, nearby)brbr• Sullivan County Fair (Liberty, nearby)brbrbrbrGetting Around:brbr- 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.brbrbrbrGetting 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.brbrbrbrRoute 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.brbrbrbrCell 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.brbrbrbrAirports:brbr• Stewart International Airport (SWF): 1 hour 40 minutesbrbr• Albany International Airport (ALB): 2 hoursbrbr• New York City Airports (JFK/LGA/EWR): 2.5–3 hoursbrbr• Wilkes-Barre/Scranton International Airport (AVP), PA: 1 hour 45 minutesbrbrbrbrPopular Landmarks:brbr• Roscoe Diner (classic eatery)brbr• Junction Pool (famous fly-fishing spot)brbr• Catskill Fly Fishing Center & Museum (nearby)brbr• Trout Town USA Park (recreation)brbr• Roscoe O&W Railway Museum (railroad history)brbr• Roscoe Beer Company (brewery)brbr• Beaverkill Covered Bridge (historic, nearby)brbr• Willowemoc Creek (fishing, nature)brbr• Roscoe Campsite Park (camping, events)brbr• Catskill Scenic Trail (biking/hiking, nearby)brbr• Trout Parade (annual event)
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Bath 2

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Sleep 4

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Exceptional(3)

$372.94

/ Nightly
Private Vacation Home

Charming 4-bedroom Private Home on 5 Acres of Land with Open Mountain View’s

Roscoe, New York, United States

A fully renovated 1920’s homestead on 5 acres of gorgeous Catskills landscape. This light filled home offers four large bedrooms, a spacious living room with a fireplace; an open concept kitchen/dining area; and a screened in side porch. Outside is a large open lawn with expansive views, a natural spring, a treehouse for all ages, and an inviting fire pit. The location while rural is not remote, minutes from truly great restaurants and venues. Come enjoy this magical place!brbrThis renovated 1920's country home is just under 2000 square feet. The property maintains its original character while providing modern amenities. It is situated on 5 acres of private land including open views of the mountains and a pond. The property also includes a turn of the century barn and natural spring.brbrYou will have full access to the property, except the attic and basement storage areas. There is no access to laundry on site as the basement is not suitable for guests. There is a nice laundromat 10 minutes away in Livingston Manor.brbrWe are minutes from Roscoe, Livingston Manor, Callicoon, and Bethel Arts Center. Roscoe is situated in the Catskill Mountains where there are plenty of beautiful landscapes and outdoor activities to enjoy. The area has also recently undergone a renaissance and has a wonderfully active food, drinks, and arts scene. A few of our favorite spots to grab a drink or bite include: Upward Brewery, Seminary Hill, and the Callicoon Wine Merchant for tapas.
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Exceptional(2)

$643.05

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Private Vacation Home

Fall & Winter Comfort in Roscoe Mountain Home

Roscoe, New York, United States

Hi, I’m Anna. I’m so glad you’re here, and I’d love to welcome you to Stewart Brook Cottage! Here are a few things I think you’ll especially enjoy about the house. brbrHighlights: If a heated pool, chefs kitchen, private seasonal trout stream, and a warm, cozy home with great beds and luxury bathrooms are on your stay wish list, then this is absolutely the home for you! brbrIt’s hard to choose where to start with this property; inside is top notch, benefiting from a recent sensitive renovation. The outside is beautiful, with near vistas of hills and forests, and the location is perfect - just a few minutes to the boutique towns of Roscoe and Livingston Manor. brbrThe charming porch covered entry gives way to a large integrated living, dining and kitchen area, all anchored by probably one of the best and biggest entertaining islands in the county. It’s enormous, but super lovely to have for entertaining, perfect for large trays and platters games and jigsaws puzzles.brbrUpstairs are the three bedrooms, all spacious with lovely linens and the comfiest beds. Both bathrooms have large oversized showers, and the primary bathroom has a gorgeous oval tub, perfect for long soaks. brbrFor lunch or dinner, the quick 5 minute drive to Roscoe and 10 minutes to Livingston Manor will get you into the areas best restaurants and fun dining spots. Guests receive a copy of our personalized travel guide at time of booking, with all the insider details and owner recommendations. brbrGuests can also take advantage of the homes’ well stocked kitchen, where the professional grade appliances will no doubt contribute to the makings of many great meals. For true relaxation, we have a rota of private chefs who can come and cook something spectacular for you. The kitchen has its own great coffee bar and an adorable built in seating area to enjoy meals with views of the garden and stream.brbrIn designing the outside space the owners have thought of everything and spared nothing - pool, terrace, dining, sunbathing, and BBQ. There’s also plenty of lawn for playing and ball games.brbrLike all Upstate Place properties, this home has a pack n’ play, highchair, baby bath etc. available to make even the smallest guest’s stay welcoming and easy. brbrThe house would be ideal for a family or a group of friends vacationing together. It is also very well suited for a multi generational family. brbrFEATURES AND AMENITIES br• Gourmet chefs kitchenbr• Bright sunroom w/ office areabr• Wood-stove br• Dining area with seating for 6br• TV (living room) br• Record player and great vinyl collection br• Air conditioning (mini splits)br• Wi-Fi - very goodbrbrOUTDOOR FEATURES br• Heated pool (16’ x 40’) with sun bathing patio (May 5th-September 22nd)br• Dining with seating for 6br• Sun loungers br• Stream with seasonal trout br• Driveway parking for 4 vehicles brbrFAMILY FRIENDLY br• Pack n’ play crib and beddingbr• Highchairbr• Childrens plates, bowls, and cups br• Infant Baby Bath br• Child / baby gatesbrbrACCESSIBILITYbrWe are committed to making every stay accessible and comfortable for everyone. We offer a variety of accessibility accessories, including ramps, shower seats, chairs etc. available at no charge. Please contact us, and we’ll gladly provide a link to where you can request these items. brbrCOFFEE SET-UPbr• MoccaMaster pour over machinebr• Smeg kettlebr• Baratza grinderbr• Frother / aerator (hand held)brbrPET FRIENDLY brThis is a V.I.Pooch Pawperty and your furry friend can expect the following: br• Dog bedbr• Bowlsbr• Toysbr• Shampoobr• First aid kitbrbrLAYOUT brTwo Level HomebrMain / ground floor level has the living room, dining area, kitchen, sunroom with office area, powder room half bathroom, and a laundry room.brUpper level has the primary bedroom with en-suite bathroom, and two further secondary bedrooms, one with queen bed and one with two twin beds. There is also a second hallway bathroom with shower. brBasement level is locked and is not available to guests. brbrBEDROOMS & BATHROOMS brMain Levelbr• Bathroom 1 - Powder Room brUpper Levelbr• Bedroom 1 - Queen bedbr• Bathroom 2 - En-suite bathroombr• Bedroom 2 - Queen bed and deskbr• Bedroom 3 - 2 x Twin bedsbr• Bathroom 3 - Hallway with shower br• All bathrooms supplied with Public Goods products (shampoo, body wash, cotton balls, q-tips).brbrUpstate Place is a property management company that provides 24/7 support to guests. brbrSTAFF, SERVICES & ADDITIONAL FEESbrAvailable at an additional cost with advance notice:brPet fee (dogs only) $100 per pet per staybrCold plunge & wellness accessories $20-$200brFirewood pre-order $25 (12 logs)brMid-stay housekeeping $200brPantry and wine pre-stocking $65brGuaranteed early check-in 12pm $150 or late check-out 3pm $150, or combined $275brbrLOCATIONbrPoints of Interestbr• 3 miles to Roscoebr• 5 miles to Callicoon Hills Resort br• 7 miles to Livingston Manorbr• 8 miles to Buck Brook Alpacasbr• 18 miles to Bethel Woods Center for the Artsbr• 32 miles to Kartrite Resort and Water ParkbrbrSKI ACCESS br• 34 miles to Holiday Mountain Family Ski br• 40 miles to Big Bear at Masthope Mtn.br• 46 miles to Belleayre Mountainbr• 71 miles to Hunter Mountainbr• 72 miles to Windham ResortbrbrAIRPORTSbr• 72 miles to Stewart International (SWF)br• 107 miles to Teterboro (TEB)br• 118 miles to Westchester (HPN)br• 127 miles to Albany International (ALB)br• 128 miles to Newark Liberty (EWR)br• 131 miles to John F. Kennedy (JFK)brbrPLEASE NOTEbrAccess: The house has 2 available levels and there are 5 steps to enter the front door hence this might not be a suitable property for those who have difficulty with steps / stairs. brbrUtility Outages: As Upstate New York can see its’ fair share of inclement weather and is primarily a tree rich area with overhead power lines, please know we do not assume responsibility for utility outages during your stay. If electric, water or Wi-Fi service is impacted, we do not refund. We do keep emergency supplies at the house, and, of course, if an outage were to persist for longer than 8 hours we would allow a cancellation without penalty. brbrWeather: During the winter months there may be ice, snow, and hazardous conditions. We recommend driving a vehicle with AWD or 4WD. Please ask about the plowing schedule for the house. Most driveways are plowed at or before 3” of accumulation. Unfortunately, we have very little control over the timing of the plowing. It is weather and dependent on the vendor schedule. brbrFIRE-PIT: The outdoor fire-pit is available in spring, summer, and fall. In winter, there may be times when it is fully covered in snow. Unfortunately, because of safety rules and regulations, we need to position our fire-pits some distance from the house and it can be very hard to dig pathways to the fire-pit for safe access. We therefore do not guarantee that our fire pits will be available to guests during the snowy winter months.brbrAnimals and Pests: The house is in a rural environment and surrounded by countryside, farms and wildlife. Although it’s wonderful to observe the eagles, deer, bears, and adorable chipmunks, it can also mean you will hear coyotes and foxes at night, and encounter the less cute mice, flies, snakes, ants, bees and ticks. There is very little to be done about it, but by keeping doors closed or screened and food in its appropriate storage, unwelcome guests will stay outside where they belong.brbrCleaning Guarantee: We are very proud of our housekeeping team who go beyond both Airbnbs General Cleaning Guidelines and Airbnb’s Enhanced Cleaning Process recommendations. Because of their hard work and high professional standards, we are able to guarantee our cleaning to our guests. We take a time stamped video of the cleaned property and do not refund for any small issues found during a stay. Instead, should a guest feel that something is amiss or needs additional attention, we will gladly have a housekeeper attend the home to take care of it within 12 hours of an issue being reported.brbrPets: This property only allows dogs. brbrPlease know that we require all guests to sign a rental lease agreement.brbrAdditional Fees: Depending on their requirements, guests will be subject to the following additional fees brDog Fees - $100 per pet per staybrPool Heat - $75 per day or $450 per weekbrPlease respect all our house rules listed in the guidebook provided, as well as the privacy of this quiet community.
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Bath 2

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Sleep 6

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Exceptional(22)

$1239.95

/ Nightly
Private Vacation Home

Massive Roscoe Retreat: Great for Large Groups!

Roscoe, New York, United States

Arrange your next family reunion or gathering at this vacation rental in Roscoe! Escape the ordinary and indulge in the extraordinary with 12 bedrooms, 12 full bathrooms, 2 half baths, a stocked game room, a commercial-grade kitchen, a sauna, and so much more! Outside, you and your guests can enjoy a pool, hiking trails, and ample dining space for sunny BBQs. Plus, the home's prime location invites you to plan outings to Beaverkill River for trout fishing or Plattekill Mountain for epic skiing.brbr-- THE PROPERTY --brbr8,500 Sq Ft | Hammam Spa (Available October-May) | Commercial Kitchen | Stream/Pond On-Site | 6-Person SaunabrbrBedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Bedroom 4: Queen Bed | Bedroom 5: Queen Bed | Bedroom 6: 2 Twin Beds | Bedroom 7: Queen Bed | Bedroom 8: 2 Twin Beds | Bedroom 9: Full Bed | Bedroom 10: Queen Bed, Full Bed | Bedroom 11: 2 Twin Beds | Bedroom 12: 2 Queen Beds, Twin Daybed w/ Twin Trundle | Additional Sleeping: 2 Pack 'n PlaysbrbrOUTDOOR LIVING: Heated seasonal pool (Memorial Day-Labor Day), private yard w/ hiking trails, covered picnic area, gas grill, wood-burning fire pit (wood not provided), deck, Adirondack chairs, speakers, hammock, screened porch brINDOOR LIVING: 2 fireplaces (decorative only), multiple dining tables, in-house music system w/ independent volume controls, movie room w/ 80 Smart TV, coffee station w/ single-serve coffee maker + drink fridge, board games/books, wood-burning saunabrGAME ROOM: Pool table, ping-pong table, foosball table, chess/checkers, basketball game, 3 arcade games, Skee-Ball, poker tablebrMUSIC ROOM: Drums, 5 guitars, karaoke machine, piano, 65 Smart TVbrKITCHEN: 2 dishwashers, 2 refrigerators, freezer, pizza oven, 6-burner stovetop, convection oven & 36-inch grill w/ ventilation system, conveyor-belt toaster, blender, mixer, Bunn coffee system w/ complimentary coffee, espresso machine, baking pans, garbage compactor, ultra-filtered water, cooking basics, dishware + flatwarebrGENERAL: Free WiFi, linens/towels, hot water heating system, individual A/C + heating units (bedrooms + common areas), 2 high chairs, iron/board, hair dryer, trash bags + paper towelsbrFAQ: 4 exterior security cameras (facing out), optional nightly pool heat fee (paid pre-trip, applied to entire stay)brACCESSIBILITY: Multi-level home, 1 step to enter, 1 bedroom/1.5 bathrooms on 1st floor, ramp available upon request brPARKING: Driveway (10 vehicles), RV/trailer parking allowed on-sitebrbr-- THE LOCATION --brbrLOCAL ATTRACTIONS: Cooks Falls Bridge (5 miles), Roscoe Mountain Club (10 miles), Buck Brook Alpacas (12 miles), Welcome To Roscoe! (12 miles), Stone Arch Bridge Historical Park (25 miles), Bethel Woods Center for the Arts (29 miles), Monticello Raceway (36 miles)brWINTER FUN: Plattekill Mountain (50 miles), Ski Big Bear at Masthope Mountain (52 miles), Hideout Ski Slope (67 miles)brMUSEUMS: Roscoe O&W Railway Museum (9 miles), Liberty Museum & Arts Center (25 miles), Deposit Historical Museum (32 miles)brCRAFT BREWS: Roscoe Beer Co. (10 miles), Catskill Brewery (15 miles), Callicoon Brewing Company (26 miles)brAIRPORT: Wilkes-Barre Scranton International Airport (77 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smoking br- No pets allowed br- No events, parties, or large gatherings br- Additional fees and taxes may apply br- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- The seasonal private pool is only available from Memorial Day to Labor Daybr- There is an optional pool heat fee of $100/night (+ fees & taxes, paid pre-trip, applied to entire stay)br- There is no lifeguard on duty; please swim at your own riskbr- This multi-level home requires 1 step to enter. There is 1 bedroom and 1.5 bathrooms on the main level; however, stairs are required to access the remaining bedrooms/bathrooms on the lower and top levels. There is a separate entrance for the lower level located on the opposite side of the property. There is a temporary ramp available that may be placed at the 1 step required to access the front entrybr- Your safety matters. This property features 4 exterior security cameras. There is a camera located at each of the exterior corners of the home, facing out. They do not look into any interior spaces. The cameras actively record video and sound while guests are in residencebr- The Hammam Spa is available seasonally, from October to Maybr- Firewood is not provided; guests are responsible for bringing their ownbr- The 2 indoor fireplaces are decorative and not available for guest use
Bed 12

Bed

Bath 13

Bath

Sleep 30

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$380.73

/ Nightly
Private Vacation Home

3BR Chalet: Deck, Fire Pit, Gazebo, Forest Views

Roscoe, New York, United States

Summary:brbrExperience 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.brbrbrbrPlease SEE: Other things to notebrbrFor Area Details, Please SEE: The neighborhood & Getting aroundbrbr*Pet Friendly, fee applies per pet.brbrbrbrThe Space:brbrWoodland Chalet, Home Features:brbr• 3 Bedroom, 2 Bath – Available for up to 6 Guests!brbr• Expansive Deck With Grill & Outdoor Diningbrbr• Fire Pit & Gazebo In Scenic Wooded Settingbrbr• Beautiful Open Interior, Fireplace, Vaulted Ceilings & Modern Kitchenbrbr• 2 Separate Work From Home Spacesbrbr• 3rd Bedroom Offers Private Entry Foyer/Flex Space With Weight Setbrbr• Free WiFi & Smart TVbrbrbrbrNOTE: Hosting a smaller group Our 2-bedroom chalet listing is ideal for up to 4 guests and is offered at a lower rate.brbrbrbrNestled 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.brbrbrbrThis 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.brbrbrbrInside, 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.brbrbrbrBedroom 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.brbrbrbrWhether 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.brbrbrbrPlease Note: A 4WD vehicle is required to access the property during the winter months.brbrbrbr*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.brbrbrbrGuest Access:brbrWe 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.brbrbrbr• 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.brbrbrbrThe Neighborhood:brbrThe 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.brbrbrbrRoscoe, 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.brbrbrbrThings to See & Do:brbr• Things to Do: brbr- Go fly fishing at Junction Pool or Willowemoc Creek.brbr- Visit the Catskill Fly Fishing Center & Museum.brbr- Enjoy craft beer at Roscoe Beer Company.brbr- Explore the Roscoe O&W Railway Museum.brbr- Picnic or play at Trout Town USA Park.brbr- Attend the annual Trout Parade.brbr- Shop at local outfitters for fishing gear.brbr- Camp or hike in nearby state forests.brbrbrbr• Things to See: brbr- The confluence of Beaverkill and Willowemoc at Junction Poolbrbr- Catskill Fly Fishing Center & Museum’s riverside campusbrbr- Roscoe Diner’s classic neon signbrbr- Willowemoc Creek’s trout-filled watersbrbr- Beaverkill Covered Bridge’s historic wooden span (nearby)brbr- Trout Town USA Park’s riverfront settingbrbr- Roscoe O&W Railway Museum’s vintage railcarsbrbr- Rolling hills and farmland surrounding the hamletbrbrbrbr• Golf Courses: Roscoe Mountain Club, Villa Roma Resort Golf Course, Twin Village Golf Coursebrbrbrbr• Museums: Catskill Fly Fishing Center & Museum, Roscoe O&W Railway Museum, Time and the Valleys Museum (Grahamsville, nearby)brbrbrbr• Local Markets: Roscoe Farmers Market, Livingston Manor Farmers Market (nearby), Callicoon Farmers Market (nearby), Roscoe Beer Company Marketbrbrbrbr• Local Restaurants & Shoppingbrbr- Restaurants: Roscoe Diner, The Junction, Raimondo’s Restaurant & Pizzeria, Roscoe Beer Co., The Courtyard, Riverside Café, Northern Farmhouse Pastabrbr- Shops: Beaverkill Angler, Roscoe Beer Co. Shop, Catskill Flies, Prohibition Distillery Shop, Junction Pool Gifts, Roscoe General Store, Northern Farmhouse Pasta ShopbrbrbrbrAnnual Festivals & Events:brbr• Roscoe Trout Paradebrbr• Roscoe Rockland Chamber of Commerce Fall Festivalbrbr• Catskill Fly Fishing Center Summerfestbrbr• Livingston Manor Trout Parade (Livingston Manor, nearby)brbr• Callicoon Country Fair (Callicoon, nearby)brbr• Roscoe Beer Festbrbr• Roscoe Catskills Pride Festivalbrbr• Livingston Manor Ice Carnival (Livingston Manor, nearby)brbr• Delaware County Fair (Walton, nearby)brbr• Sullivan County Fair (Liberty, nearby)brbrbrbrInteraction with Guests:brbrOur 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.
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps

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Exceptional(2)

$365.03

/ Nightly
Private Vacation Home

The Ipê House: Chic Catskills Cabin, 60min to Belleayre Mountain Ski

Roscoe, New York, United States

Located in Roscoe, NY, just 2 hours north of New York City, The Ipê House has everything you need to enjoy The Catskills.brbrWhether you want to relax on the beautiful private Lake Muskoday, go hiking, eat and drink locally at farm-to-table restaurants, or just stay cozy by the fire, the house has everything you need. Come enjoy the outdoors, nature is calling.brbrIt is 1 hour from the Belleayre Mountain Ski Center, the best ski and recreation resort in New York, nestled in the gorgeous Catskill Mountains. Lots of trails, challenging slopes & snowboarding ramps, plus tubing.brbrIdeal for Short Stays | BBQ Grill | Private Yard | Spectacular Lake | Free WiFibrbrFollow us! @theipehousebrbrThe Ipê House is a two bed, two bath and a loft cabin located in Roscoe, NY in the heart of the Catskills - two hours north of New York City.brbrWe are minutes away from the shops and restaurants in Roscoe, Callicoon and Livingston Manner.brbrOozing with serenity, this home is the perfect getaway for families seeking to unplug, spend quality time together and connect with nature.brbrThe house is well appointed with everything you need for a comfortable stay, including a fully equipped kitchen, washer/dryer, a record player, board games, books, internet and a 100 projector screen.brbrPlease be respectful of our home and our belongings. A lot of time and effort has gone into making this space as comfortable as possible and we hope to share it for a long time.brbrEnjoy your stay!
Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps