Vacation Rentals By Owner In Roscoe, NY

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.

Fall & Winter Comfort in Roscoe Mountain Home

Roscoe, New York, United States

Bed

Bath

Sleeps

$1239.95

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

Massive Roscoe Retreat: Great for Large Groups!

Roscoe, New York, United States

Bed

Bath

Sleeps

$449.27

Peaceful Catskill mountains 2 hours from NYC , private fishing river, completely renovated, brand new beds, furniture and kitchen. Sonos music speakers, NEST thermostat, upgraded everything! This home is a family dream and hunting/ fishing gem, close to restaurants, breweries and shopping. River view to die for !

Roscoe Christmas Cabin on the Beaverkill River with private river access !

Roscoe, New York, United States

Bed

Bath

Sleeps

$295.35

Cozy Lake House in Charming Roscoe: Your 3-Bedroom GetawaybrbrFind your home away from home in our welcoming 3-bedroom lake house in beautiful Roscoe. Relax in the spacious living area, prepare delicious meals in the fully equipped kitchen, unwind in the TV room, and enjoy the convenience of a modern bathroom. The highlights A large deck with a BBQ grill, perfect for outdoor dining and enjoying stunning lake and woodland views. As well as this you have lake access for swimming and kayaking. brbrEnjoy easy access to lake activities like swimming and kayaking, and explore the charming town of Roscoe, featuring the celebrated Roscoe Brewery and delightful local restaurants. Nearby hiking trails and quaint towns offer endless opportunities for adventure. Stay connected with reliable WiFi throughout your stay, ensuring a seamless blend of relaxation and convenience.brbrOther local attractions include, Buck Brook Alpacas, Bridal Hill Farms for horseback riding, hiking, Bethel Woods, local towns with shops and restaurants.

Cozy Lake House in Charming Roscoe: Your 3-Bedroom Getaway

Roscoe, New York, United States

Bed

Bath

Sleeps

$140.06

Escape to Nature’s Comfort in Roscoe NY. Discover the perfect blend of nature & luxury with or premium glamping adventure in Trout Town USA.. our Tiny Huts offer the ideal retreat for unwinding and reconnect with the great out doors. Located just 30 minutes from Bethel Woods concert venue, our Tiny Huts are perfect for weekend getaway or a concert adventure.brbrThe Tiny Hut features:br*Electric fireplace 4 cozy evenings br* Sofa that pulls out into a full size bedbr* WiFi to keep you connected and streaming br* Light/fan combo 4 your comfortbr* Coffee station to kickstart your adventure br* Black out roller shades 4 privacy and deep sleepbrbrOutside your Hut, enjoy:br*BBQ/fire pit 4 cooking and sitting under the starsbr* Punic table 4 outdoor diningbr* Firewood available 4 purchase on-site br* bring your stocked cooler, charcoal & lighter fluidbr* Bath house with a shower/ Toilet well stocked brbrDiscover the unique charm of our themed tiny houses at Roscoe Tiny Homes:brbrProperty of Bigfoot: Unwind in a cozy retreat that pays homage to the elusive legend. brbrCluckin’ Crazy Chicken Coop: Enjoy a whimsical stay in our delightful chicken-themed tiny house.brLoose My Mind in the Woods: Lose yourself in nature with all the comforts you need.brbrEach tiny house is ready to be booked and offers a picnic table, barbecue, and fire pit. Come check us out and enjoy a great stay!brbrBook your stay and experience glamping @ its finest in Roscoe, NY seasonal available April-November brFishing season though hunting season perfect location 4 adventure

Roscoe Coop Clucking Crazy Hut

Roscoe, New York, United States

Bed

Bath

2

Sleeps

$224.89

Nestled in the Catskills, this serene cottage has beautiful lake and mountain views and plenty of wild life. There is no shared space here--guests have access to the whole house (1,500 s.f.), as well as outdoor patio space, front and back yards, and the lake front lot across the quiet street. Guests also have access to kayaks, paddles and life jackets.brbrInside the cottage you will find a cozy living room with a fire place, a fully equipped kitchen with a washer/dryer, 1.5 baths, and three large bedrooms. Recent renovations include new flooring in the living room and most bedrooms, quartz countertops and brand new furniture and furnishings. brbrEach of the two bedrooms on the main floor feature custom built, solid wood queen beds with memory foam mattresses. One bedroom is equipped with a solid wooden desk with a chair for working from home, and the other bedroom has a weight/sit up bench and resistance bands for home exercise. The cottage has WiFi and a reliable back up generator to ensure that you're still able to work during power outages. The large upstairs bedroom is suitable for kids and adults alike, and has two double beds and a half bath. brbrIn the living room you will find a recliner sofa, a custom built wooden coffee table in front of the fireplace with a wood burning stove insert, and a custom built, bar height, dining table with four, fabulous green metal stools. Take in the gorgeous parkland and wildlife views and from the large bay window in front of the dining table as you sip your morning coffee. The cottage also has a covered front porch at the front of the house with panoramic views, and just outside, guests have access to a large stone patio with a fire pit, and an outdoor fireplace, and Adirondack chairs for relaxing around the fire. Private lake access through the empty lot across the quiet street, and kayaks, paddles and life jackets are available, weather permitting. brbrThe wood shed has firewood for guests to use.

Cottage

Rustic Catskills Cottage with Lake Access

Roscoe, New York, United States

3

Bed

Bath

6

Sleeps

$429.78

Our mountain home is a newly built house secluded in the woods and perfectly set up for families, couples, or friends to enjoy time away from the city brbrThe home has an open layout with sliding doors leading to mountain views. The stone patio faces an opening between the pines where the sunset can be watched each evening. Spend your days fishing, kayaking, hiking and then gather by the fire pit beneath a sky full of stars. brbrThe house is set at the end of a quiet road. You will feel secluded and private with a feeling of being nestled in nature. The home has modern finishes and cozy spaces make it warm and welcoming. The decor is a blend of cabin aesthetics with wood clad walls and modern conveniences. There is airconditioning, bedroom fans, wifi etc. brbrThe home is outfitted fully equipped kitchen with high-end appliances, speaker, pool table, electric fireplace, coffee maker, plush linens, board games, books, and a smart TV with Netflix/Amazon Prime.brbrGuests enjoy full access to the entire home, including: a large deck with outside dining, bedroom balconies on the stone patio, gas grill, fire pit, and high-speed WiFi (perfect for working remotely… with a view!).brbrMaximum 6 adults. Bunk beds are for children only and not designed for adults. brbrBottom floor: two bedrooms, each with sliding glass doors leading to the stone deck overlooking the mountain / sunset, one king and one queen bed with plush mattresses, premium linens, and custom new full bathroom. One bedroom with bunkbeds for the kids :) brbrTop floor: modern yet cozy top floor boasts house-wide views of the mountain, dining room, fully appointed modern kitchen, full bathroom and one queen bedroom.brbrNEARBY:brThe house is 10 minute drive to Roscoe, 20 to Livingston Manor and 30 to Calicoon. brbrFISHING!!! Access to the Beaverkill 3 mins away at bottom of baker hill road! The Beaverkill is world renowned and widely known as the birthplace of American fly fishing. There are endless lakes and you will be very close to the Beaverkill, Delaware river and Pepacton Reservoir. CBS calls Roscoe “the best trout fishing in America”.brbrIn nearby Roscoe, you’ll find incredible local restaurants, breweries, distilleries, golf courses, wineries, and even an alpaca farm. Livingston Manor and Calicoon are closeby and have incredible restaurants and cute upstate stores. brbrSKIING!! Belleayre and Plattekill mountains are just under an hour drive from the house and can be enjoyed all through the winter season. brbrNOTES:brbrNo pets allowedbrbrTravel crib available.brbrPlease know we will make ourselves available if you have any concerns or if anything is needed - just call / text us.brbrOur home is a quiet, close-knit community, so if you're planning to party, please book elsewhere :) brbrThe only thing we ask is that our guests are respectful of our home, belongings and neighbors. A lot of time, effort and resources have gone into making our home as special and as comfortable as possible. brbrOur home is nestled on a beautiful Catskill mountainside, offering stunning views and a true nature escape. With this setting comes natural slopes, stairs and some hilly terrain, so those with accessibility concerns should keep this in mind.

Roscoe Mountain Cabin

Roscoe, New York, United States

Bed

Bath

Sleeps

$163

Discover the perfect blend of nature and luxury w/ our premium glamping experience in the heart of Roscoe, NY Trout Town USA. brOur Tiny Huts offer the ideal retreat for those looking to unwind & reconnect with the great outdoors, without sacrificing the comforts of home.brbrThe Tiny Hut Features:brbr•Electric fireplace for cozy eveningsbr• WiFi to keep you connectedbr• Light/fan combo 4 your comfortbr• Coffee station 2kickstart your morningsbr• Sofa that pulls into a full-size bed with clean bedding provided.br• Cast Iron pan for use of the Charcoal grillbr• bbq combo fire pitbr• Picnic tablebr• Wine glass and openerbr• Plates, bowls, cupsbr• Electric Candles for ambiance br• Private blackout Roller Shadesbr• We provide Coffee, Tea, Sugar, flour, Salt & Pepper br • Please bring Cooler with all your food, drinks and ice. br• Please bring Charcoal lighter Fluid if you plan on bbqing br Discover the unique charm of our themed tiny houses at Roscoe Tiny Homes:brbrProperty of Bigfoot: Unwind in a cozy retreat that pays homage to the elusive legend. brbrCluckin’ Crazy Chicken Coop: Enjoy a whimsical stay in our delightful chicken-themed tiny house.brWho’s My Mind in the Woods: Lose yourself in nature with all the comforts you need.brbrEach tiny house is ready to be booked and offers a picnic table, barbecue, and fire pit. Come check us out and enjoy a great stay!

Woods I GO 2 Lose my Mind Roscoe

Roscoe, New York, United States

Bed

2

Sleeps

Exceptional(7)

$700.06

Escape to our secluded A-frame tucked away in the Catskills on 25 private acres in Roscoe, NY. Perfect for couples seeking a romantic getaway with a touch of adventure, this hidden gem offers a unique experience right from the start. Guests park at the base of the property and use a provided UTV to journey up a scenic private trail through the woods to reach the cabin — a fun and unforgettable way to begin your stay.brbrInside, you’ll find a warm, thoughtfully designed space with a king-size bed, Wi-Fi powered by Starlink, and a fully stocked kitchen ready for home-cooked meals. Curl up with a book, stream your favorite shows, or break out a board game for a cozy night in. Step outside and soak in the private hot tub under a sky full of stars, surrounded by nothing but nature and quiet — no neighbors in sight.brbrWhether you’re here to unplug and recharge, explore local hiking, or simply relax with your partner in peace, this is the spot. The A-frame is ideal for anniversaries, proposals, or just escaping the city for a while. It’s privacy, comfort, and a little bit of wild wrapped into one unforgettable stay.brbrBook your adventure today and discover your new favorite hideaway in the Catskills.

25-Acre Private Retreat w/ UTV, Hot Tub, Fire Pit, Trails & Stunning Views

Roscoe, New York, United States

2

Bed

Bath

4

Sleeps

$380.73

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.

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

Roscoe, New York, United States

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$176.44

The Cabin sits on six acres with views of the pretty Catskill forest on all sides. Excellent Hiking, Fly Fishing, Canoeing as well as some good restaurants are close-by. Our cabin is perfect for one or two couples looking to escape the city, relax and retreat in nature.brbrWhile there are many things to do, sitting on the Deck with a cup of coffee or a glass of wine, and a good book or some good company are by far the best things that happen here.brbrThe cabin sits high in the mountains surrounded by trees on all sides so you will truly feel 'away from it all'. And so, while there is good cell coverage with ATT (and somewhat less so with Verizon), there is no WiFi here. Bring your friends, your dogs, take along a book or watch a movie, build a fire, cook something great on the grill, eat outside under the stars, dance, play music... talk to each other!brbr**There are open railings around the deck as you can see in the photos. This may be an issue for small children, please contact me with questions**

Cosy, secluded cabin in the Catskill Mountains.

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$507.79

Tucked away up a wooded hillside, is our beautiful home less than a mile from Roscoe's main street, Stewart Ave. Enjoy the convenience of being downtown while feeling secluded in the privacy of 6 forested acres.brbrExplore Trout Town USA and the great outdoors with tons of fishing, waterfalls, and nature hikes nearby. Experience great shopping, food andbrdrinks along our main street and neighboring towns, or just snuggle up with a good book on the couch.brbrRoscoe offers great food and drink options and shopping but is centrally located to neighboring towns like Livingston Manor and Callicoon for even more choices! Always confirm open hours and days online.brbrPlenty of hiking trails for all levels and distances. Hunt for waterfalls, tube down a lazy river, or swim in a lake!brOf course, if you love fishing then Roscoe is the place to be. We’re not called Trout Town USA for nothing!brbrOur nearest Ski mountain is Belleayre Mountain Ski Center about 40 min away. Or Holiday Mountain (much smaller) about 30 minutes away.brbrDon’t forget to check out Bethel Woods Center For The Arts for any concerts that may be happening during your stay.brbrStart making memories!brbr(LGBTQ+ owned)brbrCheck us out on the gram for more photos!br@RoscoeHillHouse

Spacious House on a Hill in the Heart of Roscoe NY

Roscoe, New York, United States

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$329.93

Welcome to Hearthwood Hollow, a charming, rustic 3 bed/2 bath cottage in the Catskills with lots of character, nooks, and crannies. Just 2 hours from NYC, our home offers the best of both worlds: peaceful nature and close-to-town convenience. Nestled in Roscoe (aka Trout Town USA with some of the best fishing in the country), it’s a perfect weekend escape. Spend your days outdoors or exploring local towns, and unwind at night in front of the fireplace or the fire pit under the stars. Feel free to reach out to us during your stay – we’re happy to suggest local spots to check out.

Cottage

Charming 3-bedroom cottage in Roscoe for a relaxing Catskills stay

Roscoe, New York, United States

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$324.68

Quiet and cozy 3 BR Lakehouse on beautiful mountain in Roscoe NY. Enjoy golf, fishing , biking, hiking, kayaking, wildlife and campfires! Great restaurants and entertainment in town. Fully stocked kitchen, linens and bedding. Just bring your own food!!

Cozy Roscoe Lakefront Cabin

Roscoe, New York, United States

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$480.7

Enjoy the mountain and the river all seasons throughout the year and relax with the whole family at this peaceful place to stay. Overlooking historic Beaverkill Covered Bridge where can enjoy fishing, swimming, hiking and outdoors.

Beaverkill Bridge Moutain House

Roscoe, New York, United States

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$320.35

Located in Trout Town USA ! Secluded, 1600 sq ft log home, 3 bedrooms, 2.5 baths on 5 private acres. Magnificent year round Catskill Mountain views. Beaver kill River is 5 minutes away!brbrStunning indoor fireplace, relaxing front porch and large back deck with gas BBQ. Internet and satellite T.V. in bedrooms, with Netflix and HBO. Spacious outdoor, w/ gazebo, hammock , picnic table & hot tub!brbrLess than 2hrs from 2hrs from the GWB this is a great year round getaway!brbrWe usually do not meet guestsbrEsp with keyless entrybrWe are always just a call or text awaybrbrPeaceful and quitebrThere are some homes on the mountainbrbut most homes are vacation homesbrbrMost things are just 20 min away restaurants, markets, attractions, etc...brbrThe cabin is keyless brUse the keypad on the front door on the porchbruse your code to code to come and go as you pleasebrThe door automatically locks when closedbrbr1600sq ft home on 5 acresbrEverything in the cabin is for guests usebrRobes, slippers, ketchup, etc..brbrFree Keurig Varity K-cupsbrFree Expresso Varity K-cupsbrFree pot coffee we some or Bring you favorite brandbrbrWood is $15 per bundlebrWine is $20 per bottlebrbrbrbrA car is neededbrNo public transportationbrTaxi service is availablebrbr20 minutes away from most things ..markets, attractions, restaurants..etc..br#Getbacktonature

Secluded Mountain top

Roscoe, New York, United States

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$268.63

Escape to Our Rustic Farmhouse Cottage in Roscoe, NYbrbrWelcome to our newly renovated 800 sq ft Rustic Farmhouse Cottage, a perfect getaway in Roscoe, New York—known as Trout Town USA. Our peaceful retreat is just 14 miles from Bethel Woods Concert Venue, offering a beautiful, traffic-free drive through the mountains.brbrSpecial Offer:brbr • Book early for concert season and holidays. Enjoy a complimentary bottle of wine as our thank you for choosing Roscoecabinpetfriendly!brbrProperty Highlights:brbr • Located on 6 acres of scenic land with trails and a pond full of fish and frogsbr • Close proximity to Tenannah Lake and Lake Muskoday, both within walking distancebr • 3.5 miles to Crystal Lake Forest with a public lake, beach, and extensive hiking trailsbrbrOutdoor Activities:brbr • Local trout fishing, hunting, hiking, bird watching, canoeing, kayaking, and tubing down the Delaware Riverbr • Visit nearby waterfalls and Mud Pondbr • Alpaca farm tours (10 minutes away, book in advance)br • After a day of adventure, relax under the stars with a bonfire at the fire pit (wood provided at no charge)brbrLocal Attractions:brbr • Explore the town of Roscoe, just 4 miles down the mountain, featuring great restaurants, shops, and the Roscoe Brewery with live music on weekendsbr • Visit The Courtyard, a bar and restaurant with live music in the summer, overlooking the mountains and golf coursebrbrCottage Amenities:brbr • Fully stocked with board games, corn hole, extra clean towels, toiletries, and kitchen essentialsbr • Large deck overlooking the pond, perfect for remote work with strong WiFibr • Kitchen includes spices, coffee, tea, sugar, a cold case of water, charcoal for BBQ, and morebr • Open concept living room, dining room, and kitchenbr • 2 bedrooms: master with a queen-size bed, second bedroom with two full-size bunk beds (sleeps up to 4 children or 2 couples)br • Handicap accessible with ramp and wide doorsbrbrPet-Friendly:brbr • No pet fee (2 dog maximum)br • Dogs must be well-trained, off-leash, multi-dog, and human friendly (no full breed Pit Bulls, German Shepherds, or Dobermans due to insurance restrictions)brbrGuest Experience:brbr • Hosts Mike & I live on the property with our friendly boxer mixes, ensuring privacy and assistance as neededbr • Social distancing practices are in place for your safetybr • Personalized recommendations for local attractions and dining in Roscoe, Callicoon, and Livingston Manorbr • Assistance with bonfires and any special requestsbrbrAdditional Accommodations:brbr • Also available on the property: a cabin and a luxury RV, each with private fire pits, decks, and BBQ areasbrbrAddress:br68 Trout Brook Road, Roscoe, NY 12776brbrBook Your Mountain Getaway Today!brEnjoy a serene escape with plenty of activities, privacy, and comfort. We look forward to hosting you and your furry friends soon at Roscoecabinpetfriendly!

Cottage

Roscoe Cottage Pet Friendly

Roscoe, New York, United States

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$181.5

This Roscoe camper boasts 1 inviting bedroom with a king bed. Guests can relax in the charming living room, which features a comfortable sofa bed for extra sleeping space. The kitchen is fully equipped set with a dining table. The bathroom includes a refreshing shower and a handy hair dryer. Whether you’re warming up with the heating or cooling down with the AC, this brilliant space ensures an enjoyable stay. Cozy and well-equipped, it’s the perfect spot to unwind after a day of adventure. We look forward to hosting you at our place.

Cozy Camper at Roscoe Wildlife Retreat

Roscoe, New York, United States

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4

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$141.38

Discover this 1 bedroom apartment in Roscoe. The space offers a soothing atmosphere where guests can relax after a day of exploring. With heating and AC, comfort is always within reach. A superb fitness room is available for those who like to stay active. The bathroom is clean and functional, perfect for refreshing yourself. Whether you’re unwinding or getting ready for the day, this serene retreat provides everything you need. A great place to call homebase while you’re away, we hope you enjoy your stay.brThis rental is attached to another property that is occupied. It is not a shared apartment. The property the rental is on is shared with the manager.

Apartment

Charming 1 bedroom apartment with AC in quaint Roscoe

Roscoe, New York, United States

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