Home Vacation Home Rentals By Owner In Roscoe, NY

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$971.21

/ Nightly
Private Vacation Home

NEW: Multi-Generational Haven nr Roscoe

Roscoe, New York, United States

Hi, I’m Anna. I’m so glad you’re here, and I’d love to welcome you to The Lodge at Roscoe Peak! Here are a few things I think you’ll especially enjoy about the house. brHighlights: If your dream getaway includes airy, modern interiors, a cozy fireplace, foodie and brewery stops in charming Roscoe, kid-friendly adventures close by, and plenty of room to gather with friends or extended family—welcome to your perfect upstate escape.brbrJust a few minutes from downtown Roscoe, this spacious and beautifully designed lodge-style cabin offers the best of both comfort and convenience. Whether you`re planning a multi-generational family trip or a weekend retreat with friends, The Lodge at Roscoe Peak delivers space, style, and all the thoughtful touches that make for a seamless stay.brbrStep inside to soaring ceilings, big windows, and a bright, open-plan layout that’s perfect for relaxing together. The double-height living room features panoramic views of the backyard, comfy seating for gatherings or game time, and an easy-to-use wood-burning fireplace that adds warmth and charm.brbrThe heart of the home is a large, well-equipped chef’s kitchen with a peninsula island for casual seating and a dining area that comfortably seats 10—perfect for shared meals and conversation.brOn the main level, you`ll find two serene king bedrooms, one of which includes an en-suite bathroom with an oversized soaking tub—ideal for unwinding after a day of exploring. A nearby powder room adds convenience.brbrDownstairs is where the fun continues: a spacious TV and playroom area make it a hit with kids and teens, and two oversized bedrooms provide flexible sleeping arrangements. One has two bunk setups (with full-size beds on the bottom and twins on top), and the other features two queen beds plus a full-size crib. These rooms share a modern hallway bathroom.brbrOutside, enjoy a private backyard with a large lawn, perfect for games and running around, as well as a spacious deck with dining, lounging, and a fire pit with Adirondack chairs. Whether you’re grilling with friends or stargazing with family, the outdoor space is just right for all ages.brbrAnd the location Spot on. Buck Brook Alpacas is just a mile down the road and always a hit with children. Bethel Woods Center for the Arts, water parks, and some of the Catskills’ best small towns are just a short, scenic drive away.brbrAs with all Upstate Place properties, The Lodge at Roscoe Peak is stocked with family essentials, including a pack ’n play, highchair, crib, baby bath, and children’s dishware to ensure even the tiniest brguests feel right at home.brbrThis is a home that works beautifully for extended families, multiple families traveling together, or a group of friends looking to unwind in nature without sacrificing style or comfort.brbrFEATURES AND AMENITIES br• Full kitchenbr• Wood burning fireplace (wood provided)br• Dining area with seating for 10br• Washer / dryerbr• Lower level media / playroombr• Wi-Fi - excellentbrbrOUTDOOR FEATURES br• Hot-tubbr• Deck - partially coveredbr• BBQ (propane provided)br• Outdoor dining seating for 10 br• Firepit (wood provided)br• Driveway parking for 8 vehicles brbrBREAKFAST brEnjoy Good Morning, Upstate—a complimentary first-day breakfast stocked just for you! brbrCOFFEE SET-UPbr• Moccamaster pour over coffee makerbr• Electric kettlebr• Grinderbr• Frother / aerator (hand held)brbrFAMILY FRIENDLY br• Crib plus Pack n play 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. 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, 2 bedrooms, large full bathroom with shower and separate tub, powder room and laundry area / mud room.Lower level is a full walk-out and has a media room, play area, 2 bedrooms, and a shared hallway bathroom.brbrBEDROOMS & BATHROOMS brMain Levelbr• Bedroom 1 - King bed br• Bedroom 2 - King bed br• Bathroom 1 - large en-suite to primary bedroom with separate tub and showerbr• Bathroom 2 - powder room with WC and sinkbrLower Levelbr• Bedroom 3 - 2 x queen bedsbr• Bedroom 4 - 2 x bunk beds, both with lower full size mattresses and twin uppersbr• Bathroom 3 - hallway bathroom with tub / shower combobr• The bathrooms are 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 $235brPantry and wine pre-stocking $65brGuaranteed early check-in 12pm $150 or late check-out 3pm $150, or combined $275brbrLOCATIONbrPoints of Interestbr• 1 mile to Buck Brook Alpacasbr• 2 miles to Roscoe Mountain Clubbr• 5 miles to Main St Roscoebr• 12 miles to Livingston Manorbr• 16 miles to Bethel Woods Museumbr• 35 miles to Kartrite Indoor Water Park brbrSKI ACCESS br• 35 miles to Masthope / Big Bearbr• 37 miles to Holiday Mountainbr• 49 miles to Belleayre Mountainbr• 74 miles to Hunter Mountainbr• 75 miles to Windham ResortbrbrAIRPORTSbr• 70 miles to Scranton Wilkes Barre (AVP)br• 75 miles to Stewart International (SWF)br• 110 miles to Teterboro (TEB)br• 131 miles to Newark Liberty (EWR)br• 121 miles to Westchester (HPN)br• 122 miles to Albany International (ALB)br• 136 miles to John F. Kennedy (JFK)brbrPLEASE NOTE - brCancellation and Insurance: We encourage all our guests to purchase travel insurance, whether through the OTA when offered at the time of booking, or through a third party. We cannot make any exceptions to our cancellation policy.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. 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.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. All our properties benefit from scheduled pest control, but we are in a natural environment and we can not fortify the houses or gardens completely. 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 time stamped video and photos of the cleaned property and do not refund for any small issues found during a stay. Should a guest feel that something is amiss or needs additional attention, we will have a housekeeper attend the home to take care of it within 12 hours of an issue being reported. brbrRental Agreement: Please know that we require all guests to sign a rental lease agreement. brbrPets: This property only allows dogs. brbrThis house has two levels and may not be suitable for guests who don’t wish to use stairs. However, it does have 2 ground/ main level bedrooms and a bathroom. brbrAdditional Fees: Depending on their requirements, guests will be subject to the following additional fees brDog Fees - $100 per pet per staybrbrWe look forward to welcoming you to The Lodge at Roscoe Peak!brPlease respect all house rules listed in the guidebook provided, as well as the privacy of this quiet community.
Bed 4

Bed

Bath 2

Bath

Sleep 12

Sleeps

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$689.63

/ Nightly
Private Vacation Home

Modern House - 100 Acres w/ Waterfall & Hiking

Roscoe, New York, United States

Hi, I’m Anna. I’m so glad you’re here, and I’d love to welcome you to Howard’s Hill! Here are a few things I think you’ll especially enjoy about the house. brbrHighlights: Beautiful luxury home with chef`s kitchen on 100 acres. Exceptional privacy and seclusion, yet minutes to Roscoe. brbrWelcome to Howard`s Hill! If you want a contemporary country home with sleek interiors near a great town, this is it! brbrDesigned by Warren Freyer of Freyer Collaborative, the house was sited towards the hill`s peak to benefit from great light and cool breezes and, most importantly, provide an immersive experience with the birds and nature. Eagles are regular visitors! Located on 100 acres, guests can experience the ultimate Catskill living, with woods, a private waterfall, and stunning rugged terrain, before coming inside to enjoy many luxury features. brbrThe house is extraordinary, with voluminous spaces, polished concrete heated floors, and excellent sight lines. Shoji screens that disappear into the walls can come out to provide a cozier feeling and dilute the intense natural light. brbrThe layout is centered around two enormous square pavilion-type spaces. On entering, to the right, you see the cavernous living area with a 30 ft peaked ceiling. With walls of windows on all sides, a lovely fireplace, and a fabulous kitchen with Sub Zero and professional appliances, this great room will allow for a magical gathering. To the left, the hallway leads to the two sleeping areas. This property is technically a one-bedroom house, but its vastness and clever use of shoji screens provide privacy, and here on the main level, it creates two bedrooms (please see the floor plan in photos). Each area has a queen bed and views of the forest. Also on this floor is a shared hallway bathroom with a shower and a separate laundry room. Upstairs is the grand principal bedroom suite. Facing east and surrounded by windows, you will feel like you are sleeping in the clouds. This suite has a bathroom with a shower and a sitting area for a quiet moment. Or maybe not so quiet - the owner enjoys playing in the morning, and this is where they keep their beautiful piano. brbrBack downstairs, you have a good-sized deck set amongst the trees. Dining for 8, sofa seating, and the BBQ are all here. In addition, there is a lawn garden area at the front with a firepit and forest views. brbrTHE KITCHEN & MEALS brMeals and beverages are a breeze. The kitchen has one of the best-equipped coffee stations, with every type of machine (Nespresso, Expresso, Keurig, regular, French press, drip) and appliances for frothing and grinding. Cupboards hold an enormous array of equipment for any culinary endeavor. For the less adventurous, a great dinner can also be had by driving 10 minutes in either direction. For the best picnic spot in the county, the vast rock ledge next to the waterfall gets five stars!brbrFAMILY & FUN brLike all Upstate Place properties, this home has a crib, highchair, baby bath, etc., to make the smallest guest`s stay welcoming and easy. The house provides well for all activities: towels and picnic blankets for the waterfall, snowshoes for winter walks, snacks for nibbles, and propane and firewood for outdoor living. brbrIdeally, the house would suit a family, a small group, or couples vacationing together. brbrFEATURES AND AMENITIES br• Gourmet chefs kitchenbr• Main level bedrooms br• Dining area with seating for 6br• TVbr• Work/office areabr• Books & gamesbr• Wi-Fi - very goodbrbrFAMILY-FRIENDLY br• Crib and beddingbr• Highchairbr• Booster seat br• Children`s plates, bowls, and cupsbr• Toys and gamesbr• Baby Bathbr• 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. brbrLAYOUT brTwo Level HomebrThe main level has the entry, great room - living, kitchen, dining, two sleeping areas, bathroom, and separate laundry room. brThe upper level has a main bedroom, an en-suite bathroom, and a sitting area. brbrBEDROOMS & BATHROOMS br• Bedroom 1 - Main level, Queen bed br• Bedroom 2 - Main level, Queen bed br• Bathroom 1 - Hallway access w/ shower br• Bedroom 3 - Upstairs King bedroombr• Bathroom 2 - Upstairs, Shower, walk-in br• Bathrooms supplied with full products (Le Labo shampoo, conditioner, body wash, cotton balls, q-tips, etc.)brbrOUTDOOR FEATURES br• Private Garden and woodsbr• Stunning waterfallbr• Deckbr• Outdoor dining for 8br• Firepit - wood providedbr• Lawnbr• Outdoor seatingbr• Barbecue grill - propane providedbr• Driveway parking for five vehicles brbrPET FRIENDLY brThis is a V.I.Pooch Pawperty! There is a $100 pet fee per pet and your furry friend can expect the following:br• Dog bedbr• Bowlsbr• Toysbr• Poop bagsbr• Shampoobr• First aid kitbrbrUpstate 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 $175brPantry and wine pre-stocking $65brGuaranteed early check-in 12pm $100 or late check-out 3pm $100, or combined $175brbrLOCATIONbrPoints of Interestbr• 3 miles to The Catskill Hills Resortbr• 4 miles to Roscoebr• 7 miles to Buck Brook Alpacasbr• 7 miles to North Branchbr• 9 miles to Livingston Manorbr• 15 miles to Mud & Trout Pond Hikingbr• 16 miles to Bethel Woods Concertsbr• 18 miles to Mongaup Pond Birding Trailbr• 34 miles to Kartrite Indoor Water ParkbrbrSKI ACCESS br• 30 miles to Holiday Mountainbr• 37 miles to Big Bear at Masthope Mtnbr• 48 miles to Belleayre MountainbrbrAIRPORTSbr• 73 miles to Wilkes-Barr Scranton (AVP)br• 74 miles to Stewart International (SWF)br• 109 miles to Teterboro (TEB)br• 120 miles to Westchester (HPN)br• 121 miles to Albany International (ALB)br• 129 miles to Newark Liberty (EWR)br• 136 miles to John F. Kennedy (JFK)brbrPLEASE NOTE - brCancellation and Insurance: We encourage all our guests to purchase travel insurance, whether through the OTA when offered at the time of booking, or through a third party. We cannot make any exceptions to our cancellation policy.brbrRental Agreement: Please know that we require all guests to sign a rental lease agreement. 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” or more accumulation but we cannot guarantee an exact time for the plowing as the crews are often unreachable and out of cell service areas for much of the day. brbrThis house has a steep / and or long driveway and extra caution is warranted. Please allow extra time when departing. Upstate Place does supply snow shovels and pet-friendly salt at each of our properties for extra safety. 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. All our properties benefit from scheduled pest control, but we are in a natural environment and we can not fortify the houses completely. 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.brbrThis home may have weekly lawn and trash services as well as monthly pest control service. Service providers may access the exterior front yard and back yard during your stay to ensure the home is properly maintained.brbrAdditional Fees: Depending on their requirements, guests will be subject to the following additional fees brDog Fees - $100 per pet per staybrPlease respect all our house rules listed in the guidebook provided, as well as the privacy of this quiet community.
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps

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Exceptional(2)

$429.93

/ Nightly
Private Vacation Home

Hot Tub, Fire Pit, 5 Acres | Cabin + Tiny House

Roscoe, New York, United States

Summary:brbrTwo homes set on five wooded acres in the Catskills, a short drive from Roscoe and Callicoon. The renovated main house features a spacious deck for grilling and dining, while the modern guesthouse offers a private retreat with a sleeping loft, kitchen, bathroom, large sundeck, and its own driveway—perfect for reconnecting with nature and loved ones.brbrbrbrPlease SEE: Other Things to NotebrbrFor Area Details, Please SEE: The Neighborhood & Getting Aroundbrbr*Pet Friendly, fee applies per pet.brbrbrbrThe Space:brbrRustic Chic Cabin + Tiny House, Home Features:brbr• 3 Bedrooms, 2 Baths - Available for up to 8 Guests!brbr• Secluded wooded setting with two separate homesbrbr• Main cabin: Hot tub, fire pit, screened-in porch, grill + outdoor diningbrbr• Tiny house includes its own wraparound deck + grillbrbr• Free WiFi by Satellite Internet & Smart TVbrbrbrbrSleeping Arrangements: brbr• Bedroom 1 - King Bed (Main House)brbr• Bedroom 2 - Full Bed (Main House)brbr• Bedroom 3 - Queen Bed (Main House)brbr• Guesthouse Studio Loft: 1 King Bed (ladder access)brbrbrbrRent 2 Properties!brbrRustic Chic Cabin + Tiny House is a secluded, two-home retreat tucked into the trees—perfect for groups who want to reconnect, spread out, and actually feel “away.” Enjoy the convenience of two separate spaces on one lot, ideal for families, friends, or multi-generational stays. brbrbrbrRustic Chic Cabin (Main House)brbrThe main cabin blends rustic character with modern comfort, featuring an open-concept layout with warm wood finishes and plenty of natural light. The kitchen is a standout with matte black cabinetry, a crisp white tile backsplash, stainless steel appliances, a modern vent hood, and a farmhouse-style sink under a bright window. Gather around the oversized butcher-block island for pancake breakfasts, charcuterie nights, and après-adventure snacks. The living area is bright and airy thanks to big windows and a skylight, with a large sectional for movie nights and a cozy wood stove for classic cabin vibes. Downstairs, a second living space is perfect for games and relaxing. The cabin includes three bright bedrooms with comfortable linens and a renovated full bath that’s clean and refreshed. The main house features multiple outdoor entertainment areas including a screened-in porch, a deck with an outdoor grill and dining, a fire pit, and a hot tub. brbrbrbrTiny House (Detached Guesthouse Studio)brbrJust steps away, the tiny house adds extra flexibility with its own open living-dining space, full kitchen, bath, washer/dryer, and a lofted king bed accessed by ladder. Inside, warm wood walls and a vaulted, double-height ceiling make the space feel open and airy, while tall windows and a large picture window bring in beautiful natural light and forest views. The cozy living area includes a wall-mounted TV and a mini wood stove for chilly evenings, plus efficient heating/cooling via a ductless mini-split for year-round comfort. Sliding doors open to the wraparound deck for easy indoor/outdoor living—perfect for morning coffee, grilling, and winding down under the trees. brbrbrbrbrbr• Winter Access Notice: 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.brbr• Satellite Internet: Internet is provided by ViaSat a satellite internet company. This can cause the internet to fluctuate and possibly not allow consistent connection.brbrbrbr- This is a two home lot, while you have privacy and separation from the other house, each home is still visible from either home. There are two separate driveways for each house. brbrNeed less space for your group You can rent each of the properties individually—just message us for more information.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)brbrbrbrInteraction with Guests:brbrOur goal is to make sure your stay exceeds expectations from start to finish. Portoro Homes communicates by email and phone, and once your booking is confirmed, we’ll email your rental agreement for e-signature. Check-in instructions are sent by email and text message prior to arrival, and we offer convenient self check-in. During your stay, we’ll typically check in by text once or twice to ensure a 5-star experience, and we’re available 24/7 if any questions come up. After checkout, we’ll follow up—we’re excited to hear about your stay and welcome any feedback.
Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps

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Exceptional(5)

$222.59

/ Nightly
Private Vacation Home

Hot Tub, Fire Pit, 5 Acre View | Rustic Chic Cabin

Roscoe, New York, United States

Summary:brbrExperience this stunning, chic cabin on a two-home lot nestled among five acres of Catskills forest. Enjoy a generous deck for grilling and outdoor dining, plus WiFi, Smart TV, and thoughtful amenities for a true retreat from the city. Just a short drive from Roscoe and Callicoon, it’s a cozy, renovated home base for Catskills relaxation and exploration.brbrbrbrPlease SEE: Other Things to NotebrbrFor Area Details, Please SEE: The Neighborhood & Getting Aroundbrbr*Pet Friendly, fee applies per pet.brbrbrbrThe Space:brbrRustic Chic Cabin, Home Features:brbr• 3 Bedrooms, 1 Bath - Available for up to 6 Guests!brbr• Secluded wooded settingbrbr• Cozy wood stove + bright open living spacebrbr• Screened-in porch, hot tub, fire pit, deck w/ grill + outdoor diningbrbr• Free WiFi by Satellite Internet & Smart TVbrbrbrbrSleeping Arrangements: brbr• Bedroom 1 - King Bedbrbr• Bedroom 2 - Full Bedbrbr• Bedroom 3 - Queen BedbrbrbrbrWelcome to Rustic Chic Cabin Retreat, your quiet reset in the woods. Tucked into a peaceful, tree-filled setting, this cabin is made for slow mornings, fresh air, and cozy nights in. Inside, the open-concept layout keeps everyone connected, with warm finishes, great natural light, and a wood stove that brings classic cabin comfort when the temperature drops. The renovated kitchen is a true highlight—matte black cabinetry, a crisp white tile backsplash, stainless steel appliances, a modern vent hood, and a farmhouse sink set under a bright window. The oversized butcher-block island is the heart of the home, perfect for pancake breakfasts, prepping trail snacks, or setting out a spread while everyone gathers and chats. Just off the kitchen, the living room feels bright and inviting, with plenty of space to stretch out after a day outside, and a relaxed, rustic-chic style that feels updated without losing the cabin vibe. Downstairs, a second living space gives you extra room for games, movie nights, or a separate hangout zone. Three comfortable bedrooms and a refreshed full bath make it easy to settle in and unwind.brbrbrbrOutside is where this cabin really shines. Start your day with coffee on the screened-in porch, then fire up the grill for an easy lunch or dinner on the deck—there’s outdoor dining space so meals can be enjoyed in the fresh air. As the sun goes down, gather around the fire pit for s’mores, stories, and that classic crackling-fire ambiance under the trees. When you’re ready to fully relax, slip into the hot tub and soak while you take in the quiet, wooded surroundings—perfect for stargazing and ending the night on a high note. This is the kind of place that makes it easy to unplug, slow down, and actually feel like you got away.brbrbrbrbrbr• Winter Access Notice: 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.brbr• Satellite Internet: Internet is provided by ViaSat a satellite internet company. This can cause the internet to fluctuate and possibly not allow consistent connection.brbrbrbr- This is a two home lot, while you have privacy and separation from the other house, it is still visible from this home. There are two separate driveways for each house. brbr(Need more space for your group You can actually rent both of the properties together if you would like! Just message us for more information!)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:brbrGetting around Roscoe is part of the charm—quiet country roads trace trout streams and roll through wooded hills, so even a quick errand feels like a scenic drive. A car is essential for exploring the area comfortably, whether you’re heading to legendary fly-fishing access points, a local brewery, or nearby Catskills towns. Traffic is typically light, parking is easy and generally free, and the relaxed pace makes it simple to explore without stress.brbrbrbrRoute 17 (Quickway) makes it easy to hop to other Catskills destinations, while smaller backroads around 29 Lexie Ln lead you deeper into the landscape that earned Roscoe its “Trout Town, USA” nickname. You’ll find plenty of pull-offs and peaceful spots to pause—by the river, near a trailhead, or at a local market—especially when the light hits the hills just right.brbrbrbrWildlife sightings are common, especially at dawn and dusk, so take it slow on the winding roads. Cell service is usually reliable in town but can get spotty in more remote pockets, so downloading maps ahead of time is a smart move. With your own car, every drive around Roscoe becomes part of the getaway—unhurried, scenic, and full of small discoveries.brbrbrbrAirports:brbr• Stewart International Airport (SWF): ~1 hour 40 minutes (route/traffic dependent)brbr• Albany International Airport (ALB): ~2 hoursbrbr• New York City Airports (JFK/LGA/EWR): ~2.5–3 hours (route/traffic dependent)brbr• Wilkes-Barre/Scranton International Airport (AVP), PA: ~1 hour 45 minutesbrbrbrbrPopular Landmarks:brbr• Junction Pool (iconic fly-fishing access)brbr• Beaverkill Covered Bridge (historic, nearby)brbr• Willowemoc Creek (fishing, nature)brbr• Catskill Fly Fishing Center & Museum (nearby)brbr• Roscoe Beer Company (brewery)brbr• Roscoe Diner (classic local eatery)brbr• Trout Town USA Park (recreation)brbr• Roscoe O&W Railway Museum (local history)brbr• Roscoe Campsite Park (camping, events)brbr• Catskill Scenic Trail (biking/hiking, nearby)brbr• Trout Parade (annual event)
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$186.3

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Private Vacation Home

Catskills, 5 Acres, Large Deck + BBQ | Tiny House

Roscoe, New York, United States

Summary:brbrEnjoy this tiny home nestled among five acres of Catskills forest on a two-home lot, a short drive from Roscoe and Callicoon. Newly built and modern, the studio includes a sleeping loft (ladder access), full kitchen, bathroom, cozy wood stove, WiFi, Smart TV, and a large sundeck. A separate driveway from the second home helps maximize your privacy.brbrbrbrPlease SEE: Other Things to NotebrbrFor Area Details, Please SEE: The Neighborhood & Getting Aroundbrbr*Pet Friendly, fee applies per pet.brbrbrbrThe Space:brbrTiny House, Home Features:brbr• Studio Loft, 1 Bath - Available for up to 2 Guests!brbr• Secluded wooded setting with wraparound deckbrbr• Lofted king bed (ladder access) + mini wood stovebrbr• Full kitchen + washer/dryerbrbr• Free WiFi by Satellite Internet & Smart TVbrbrbrbrSleeping Arrangements: brbr• Studio Loft: 1 King Bed (ladder access)brbrbrbrWelcome to Chic Tiny House, a bright, modern tiny-home escape tucked into the woods—perfect for couples or solo travelers who want privacy and a true “away from it all” setting without sacrificing comfort. Inside, warm wood walls and soaring, double-height ceilings make the space feel surprisingly spacious, while tall vertical windows and a large picture window flood the home with sunshine and bring the forest views right indoors. The living area is cozy and thoughtfully styled, with a comfortable spot to unwind, a wall-mounted TV for easy movie nights, and a mini wood stove that turns chilly evenings into the coziest part of your stay.brbrbrbrThe kitchen is fully equipped for real meals, not just reheating leftovers. You’ll have a gas range/oven, stainless vent hood, open shelving, tile backsplash, and a full-size fridge—plus a dining table for two that’s perfect for slow breakfasts, a work session with a view, or a simple dinner in. For longer stays, the in-unit washer/dryer is a game changer, and efficient heating/cooling helps keep things comfortable year-round.brbrbrbrWhen it’s time to sleep, climb the ladder to the lofted king bed and enjoy that tucked-away, cabin-chic feel—especially with the loft’s windows and skylights that make the space feel elevated in every sense. And the best part Indoor/outdoor living is effortless here. Sliding doors open to the wraparound deck, so you can start your morning with coffee in the fresh air, grill dinner as the sun dips, and end the night listening to the woods in total peace.brbrbrbrbrbr• Winter Access Notice: 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.brbr• Satellite Internet: Internet is provided by ViaSat a satellite internet company. This can cause the internet to fluctuate and possibly not allow consistent connection.brbr• Amenities: The hot tub and fireplace nearby are specified use with rental of the main 3-bedroom cabin, or rental of both properties.brbrbrbr- This is a two home lot, while you have privacy and separation from the other house, it is still visible from this home. There are two separate driveways for each house. brbr(Need more space for your group You can actually rent both of the properties together if you would like! Just message us for more information!)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 are a favorite escape for anyone looking to trade city noise for fresh mountain air, forest views, and small-town charm. The region is known for scenic hikes, fly-fishing rivers, swimming holes, and winding drives with big views—especially in fall, when the foliage turns the landscape into a patchwork of color. Between outdoor adventures, you’ll find cozy cafés, local breweries, farm stands, and a laid-back, creative culture that makes it easy to slow down and settle in.brbrbrbrThis home is tucked near Roscoe, NY, a small Catskills hamlet affectionately known as “Trout Town, USA.” Roscoe is beloved for its world-class fly fishing, where the legendary Beaverkill and Willowemoc waters draw anglers from around the globe, but you don’t have to fish to fall in love with the area. Expect quiet roads, deep woods, and a peaceful pace—plus easy access to nearby towns like Livingston Manor and Callicoon for dining, shopping, and day trips. Whether you’re here to cast a line, hike and explore, chase waterfalls, or simply unplug and breathe, Roscoe delivers a nature-first Catskills experience with just the right amount of small-town charm.brbrbrbrThings to See & Do:brbr-- Explore:brbr• Stroll Roscoe’s small-town center for outfitters, cafés, and classic Catskills vibes.brbr• Take a scenic drive along the Beaverkill and Willowemoc for river views and pull-offs.brbr• Day trip to Livingston Manor for shops, coffee, and a lively little main street.brbr• Head to Callicoon for river-town charm, boutiques, and seasonal events.brbr• Stop at local farm stands and markets for fresh produce and Catskills-made goods.brbr-- Outdoor Adventures:brbr• Fly fish at Junction Pool, the Beaverkill, or Willowemoc Creek (iconic access points).brbr• Hike and explore nearby state forests and Catskills trail systems.brbr• Pack a picnic and find a quiet riverside spot to read, relax, or wade.brbr• Go birdwatching and wildlife spotting—especially early morning and near dusk.brbr• Explore seasonal swimming holes and waterways (conditions vary by season).brbr-- Local Farms & Markets:brbr• Browse the Roscoe Farmers Market (seasonal).brbr• Visit Livingston Manor Farmers Market (nearby, seasonal).brbr• Make a trip to Callicoon Farmers Market (nearby, seasonal).brbr-- Arts, Culture & Entertainment:brbr• Visit the Catskill Fly Fishing Center & Museum (nearby) for history, exhibits, and riverside grounds.brbr• Explore the Roscoe O&W Railway Museum for local railroad history.brbr• Catch seasonal festivals and community events throughout Sullivan County.brbr-- Dining & Shopping:brbr• Grab a classic bite at Roscoe Diner.brbr• Enjoy a pint at Roscoe Beer Company.brbr• Shop local outfitters like Beaverkill Angler for gear and local knowledge.brbr• Explore nearby dining in Livingston Manor and Callicoon for more options and nightlife.brbr-- Golf Courses:brbr• Roscoe Mountain Clubbrbr• Villa Roma Resort Golf Coursebrbr• Twin Village Golf Coursebrbr-- Annual Festivals & Events:brbr• Roscoe Trout Paradebrbr• Catskill Fly Fishing Center Summerfestbrbr• Roscoe Beer Festbrbr• Sullivan County Fair (Liberty, nearby)brbr• Callicoon Country Fair (Callicoon, nearby)brbrbrbrGetting Around:brbrGetting around Roscoe is part of the charm—quiet country roads trace trout streams and roll through wooded hills, so even a quick errand feels like a scenic drive. A car is essential for exploring the area comfortably, whether you’re heading to legendary fly-fishing access points, a local brewery, or nearby Catskills towns. Traffic is typically light, parking is easy and generally free, and the relaxed pace makes it simple to explore without stress.brbrbrbrRoute 17 (Quickway) makes it easy to hop to other Catskills destinations, while smaller backroads around 29 Lexie Ln lead you deeper into the landscape that earned Roscoe its “Trout Town, USA” nickname. You’ll find plenty of pull-offs and peaceful spots to pause—by the river, near a trailhead, or at a local market—especially when the light hits the hills just right.brbrbrbrWildlife sightings are common, especially at dawn and dusk, so take it slow on the winding roads. Cell service is usually reliable in town but can get spotty in more remote pockets, so downloading maps ahead of time is a smart move. With your own car, every drive around Roscoe becomes part of the getaway—unhurried, scenic, and full of small discoveries.brbrbrbrAirports:brbr• Stewart International Airport (SWF): ~1 hour 40 minutes (route/traffic dependent)brbr• Albany International Airport (ALB): ~2 hoursbrbr• New York City Airports (JFK/LGA/EWR): ~2.5–3 hours (route/traffic dependent)brbr• Wilkes-Barre/Scranton International Airport (AVP), PA: ~1 hour 45 minutesbrbrbrbrPopular Landmarks:brbr• Junction Pool (iconic fly-fishing access)brbr• Beaverkill Covered Bridge (historic, nearby)brbr• Willowemoc Creek (fishing, nature)brbr• Catskill Fly Fishing Center & Museum (nearby)brbr• Roscoe Beer Company (brewery)brbr• Roscoe Diner (classic local eatery)brbr• Trout Town USA Park (recreation)brbr• Roscoe O&W Railway Museum (local history)brbr• Roscoe Campsite Park (camping, events)brbr• Catskill Scenic Trail (biking/hiking, nearby)brbr• Trout Parade (annual event)brbrbrbrInteraction with Guests:brbrOur goal is to make sure your stay exceeds expectations from start to finish. Portoro Homes communicates by email and phone, and once your booking is confirmed, we’ll email your rental agreement for e-signature. Check-in instructions are sent by email and text message prior to arrival, and we offer convenient self check-in. During your stay, we’ll typically check in by text once or twice to ensure a 5-star experience, and we’re available 24/7 if any questions come up. After checkout, we’ll follow up—we’re excited to hear about your stay and welcome any feedback.
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$151.65

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Private Vacation Home

The Raven's Nest

Roscoe, New York, United States

Step into The Raven’s Nest, a one-of-a-kind glamping escape! Originally a repurposed 1960s truck body, this cozy cabin has been transformed into a stylish and comfortable retreat, blending retro Art Deco charm with modern comforts.brThe Ravens Nest is the perfect spot for a romantic getaway or a small group adventure. Unwind in a space that’s both nostalgic and updated, surrounded by the natural beauty of The Hidden Chalet Campgrounds, Roscoe, NY. Whether you're relaxing indoors or exploring the great outdoors, The Raven’s Nest offers a truly unforgettable stay.brSite Features: 2 Queen sized futons (refer to pricing for more than 2 occupants), a Mini Fridge, Sink with running cold water, Cooktop, Microwave TV. Fan/Space Heater are available upon request.brThe Ravens Nest is stocked with a Pot, Pan, Spatula, cups, forks, knives, plates, Firepit, Table & Chairs, on deck seating, Picnic tablebrOn the grounds you will find The Confessional-Our water flushing outhouse offers toilet, sink, bath/shower (hot/cold running water). The Loo is our cold-water outhouse (with sink). There is a small Commissary, on site, to accommodate those last-minute needs. Firewood is always available for purchase.brTHINGS TO KNOW:br• Meet with Host upon arrivalbr (all supplies will be transported to site location by Host)br• Wi-Fi is availablebr• Potable water available/Spring water on tapbr• Pets are allowed (depending on occupancy)br• 2WD accessible; 1 maximum vehiclebr• Short walk/no wheelchair accessbr• 1-night minimum stay br• Check-in: After 2:00 PMbr• Check-out: Before 12:00 PMbr• Items to remember to bring: Sheets/blankets/towels/toiletriesbr• GENTLE REMINDER: Garbage~what you bring in, you must take out
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