Home Vacation Home Rentals By Owner In Roscoe, NY

Showing 73 Of 73 Vacation Rentals
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Exceptional(1)

$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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Exceptional(4)

$138.93

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Apart-hotel

Reynolds House Inn - Motel Strip - Room 10

Roscoe, New York, United States

Built in 1902 as a tourist home the Newly Renovated Reynolds House Main Building has 7 decorated guest rooms all with private bathrooms. The Reynolds House Motel strip has 8 Rooms all with 2 Double beds and private bathrooms, In addition we have 2 New Private Suites available. Halls filled with history, comfortable guest rooms, and the surrounding beauty of the Catskills Forest Preserve, the Reynolds House welcomes you!brbrReynolds House Motel Strip has 8 rooms all with two double beds, Full Bathroom, television, air conditioning, Microwave and refrigerator. Situated in the hamlet of Roscoe, guests of the Reynolds House Inn & Motel are within walking distance of gift and antique shops, sporting stores, and several restaurants. Rooms Are newly Renovated!
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$145.77

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Motel

Reynolds House Inn - Motel Strip - Room 9

Roscoe, New York, United States

Built in 1902 as a tourist home the Newly Renovated Reynolds House Main Building has 7 decorated guest rooms all with private bathrooms. The Reynolds House Motel strip has 8 Rooms all with 2 Double beds and private bathrooms, In addition we have 2 New Private Suites available. Halls filled with history, comfortable guest rooms, and the surrounding beauty of the Catskills Forest Preserve, the Reynolds House welcomes you!brbrReynolds House Motel Strip has 8 rooms all with two double beds, Full Bathroom, television, air conditioning, Microwave and refrigerator. Situated in the hamlet of Roscoe, guests of the Reynolds House Inn & Motel are within walking distance of gift and antique shops, sporting stores, and several restaurants. Rooms Are newly Renovated!
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Exceptional(3)

$167.37

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Motel

Reynolds House Inn - Motel Strip - Room 7

Roscoe, New York, United States

Built in 1902 as a tourist home the Newly Renovated Reynolds House Main Building has 7 decorated guest rooms all with private bathrooms. The Reynolds House Motel strip has 8 Rooms all with 2 Double beds and private bathrooms, In addition we have 2 New Private Suites available. Halls filled with history, comfortable guest rooms, and the surrounding beauty of the Catskills Forest Preserve, the Reynolds House welcomes you!brbrReynolds House Motel Strip has 8 rooms all with two double beds, Full Bathroom, television, air conditioning, Microwave and refrigerator. Situated in the hamlet of Roscoe, guests of the Reynolds House Inn & Motel are within walking distance of gift and antique shops, sporting stores, and several restaurants. Rooms Are newly Renovated!
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Exceptional(5)

$167.37

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Motel

Reynolds House Inn - Motel Strip - 8

Roscoe, New York, United States

Built in 1902 as a tourist home the Newly Renovated Reynolds House Main Building has 7 decorated guest rooms all with private bathrooms. The Reynolds House Motel strip has 8 Rooms all with 2 Double beds and private bathrooms, In addition we have 2 New Private Suites available. Halls filled with history, comfortable guest rooms, and the surrounding beauty of the Catskills Forest Preserve, the Reynolds House welcomes you!!brbrbrReynolds House Motel Strip has 8 rooms all with two double beds, Full Bathroom, television, air conditioning, Microwave and refrigerator. Suite # 3 has an additional upstairs room with 2 twin beds! Great for a family! Situated in the hamlet of Roscoe, guests of the Reynolds House Inn & Motel are within walking distance of gift and antique shops, sporting stores, and several restaurants. Great for longer stays! Rooms Are newly Renovated!
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Exceptional(8)

$145.77

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Private Vacation Home

Reynolds House Inn - Motel Strip - 6

Roscoe, New York, United States

Built in 1902 as a tourist home the Newly Renovated Reynolds House Main Building has 7 decorated guest rooms all with private bathrooms. The Reynolds House Motel strip has 8 Rooms all with 2 Double beds and private bathrooms, In addition we have 2 New Private Suites available. Halls filled with history, comfortable guest rooms, and the surrounding beauty of the Catskills Forest Preserve, the Reynolds House welcomes you!!brbrbrReynolds House Motel Strip has 8 rooms all with two double beds, Full Bathroom, television, air conditioning, Microwave and refrigerator. Suite # 3 has an additional upstairs room with 2 twin beds! Great for a family! Situated in the hamlet of Roscoe, guests of the Reynolds House Inn & Motel are within walking distance of gift and antique shops, sporting stores, and several restaurants. Great for longer stays! Rooms Are newly Renovated!
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Exceptional(7)

$212.57

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Apart-hotel

Reynolds House Inn - Motel Strip - 3

Roscoe, New York, United States

Built in 1902 as a tourist home the Newly Renovated Reynolds House Main Building has 7 decorated guest rooms all with private bathrooms. The Reynolds House Motel strip has 8 Rooms all with 2 Double beds and private bathrooms, In addition we have 2 New Private Suites available. Halls filled with history, comfortable guest rooms, and the surrounding beauty of the Catskills Forest Preserve, the Reynolds House welcomes you!!brbrbrReynolds House Motel Strip has 8 rooms all with two double beds, Full Bathroom, television, air conditioning, Microwave and refrigerator. Suite # 3 has an additional upstairs room with 2 twin beds! Great for a family! Situated in the hamlet of Roscoe, guests of the Reynolds House Inn & Motel are within walking distance of gift and antique shops, sporting stores, and several restaurants. Great for longer stays! Rooms Are newly Renovated!
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Exceptional(13)

$167.37

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Motel

Reynolds House Inn - Motel Strip - Room 5

Roscoe, New York, United States

brBuilt in 1902 as a tourist home the Newly Renovated Reynolds House Main Building has 7 decorated guest rooms all with private bathrooms. The Reynolds House Motel strip has 8 Rooms all with 2 Double beds and private bathrooms, In addition we have 2 New Private Suites available. Halls filled with history, comfortable guest rooms, and the surrounding beauty of the Catskills Forest Preserve, the Reynolds House welcomes you!brbrReynolds House Motel Strip has 8 rooms all with two double beds, Full Bathroom, television, air conditioning, Microwave and refrigerator. Situated in the hamlet of Roscoe, guests of the Reynolds House Inn & Motel are within walking distance of gift and antique shops, sporting stores, and several restaurants. Rooms Are newly Renovated!
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$476.66

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Chalet

Lofted farmhouse in charming Roscoe non the Beaverkill river

Roscoe, New York, United States

Set on 7 acres overlooking the Beaverkill river, this delightful chalet style farmhouse features a central fireplace open on all sides to the open concept main floor. 3 bedrooms with a mix of queen, full, and twin beds are lofted above the main floor, with hatched windows to look below. The MBR has an en suite shower bathroom and it's own porch for a morning coffee or meal in a private loft area. Blackout curtains will let you sleep as long as you like. brbrOn the other loft there are a full bedroom and a bedroom with 2 twin beds that can be joined to form a king size bed. Another full bathroom is on the main floor with stone floors and waterfall tile in the bathtub. All bedrooms have closets and drawer space. There are multiple seating areas including a breakfast bar, a TV nook, a large DR, a scenic LR, multiple desk areas, a beautiful porch with BBQ on the main floor, 2 additional sofas in the multi use mud room/fitness area and an outdoor firepit. The property also includes a washer/dryer and WiFi. There is a badminton set and croquet set in the garage. We offer one 5 gallon water in the water cooler in addition to the well water on tap. There is hot water baseboard heat on the main floor and additionally electric radiators in the MBR. In the summer, we avoid A/C as much as possible to be light on the footprint. Even in the summer the home is cool. Please inquire if this is a must for you and we can add some units for an additional fee.brbrNestled in a peaceful setting, this rustic home is the perfect retreat for a relaxing getaway. The open seating plan on the main floor also includes a wall of windows leading on to the porch. You will be surrounded by forest sounds, light and the sounds of water gurgling from the nearby stream and river. brbrRoscoe is a hip town with lovely stores and eateries, a brewery and distillery and nearby hiking trails. Feel free to reach out to us during your stay - we're happy to suggest local spots to check out.
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Exceptional(17)

$167.37

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Apart-hotel

Reynolds House Inn - Motel Strip - Room 4

Roscoe, New York, United States

Built in 1902 as a tourist home the Newly Renovated Reynolds House Main Building has 7 decorated guest rooms all with private bathrooms. The Reynolds House Motel strip has 8 Rooms all with 2 Double beds and private bathrooms, In addition we have 2 New Private Suites available. Halls filled with history, comfortable guest rooms, and the surrounding beauty of the Catskills Forest Preserve, the Reynolds House welcomes you!!brbrReynolds House Motel Strip has 8 rooms all with two double beds, Full Bathroom, television, air conditioning, Microwave and refrigerator. Situated in the hamlet of Roscoe, guests of the Reynolds House Inn & Motel are within walking distance of gift and antique shops, sporting stores, and several restaurants. Rooms Are newly Renovated!
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$76.32

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Caravan Park/Campsite

Hole in the Wall-Bring Own Tent

Roscoe, New York, United States

The perfect escape to your own private camping nook, nestled beside a centuries-old stone wall and natural spring. This peaceful hideaway offers a rustic, off-grid experience (no electricity on this site), perfect to unplug and immerse yourself in nature. Whether you're a seasoned camper or a first-time adventurer, this hidden gem provides the perfect backdrop for a relaxing, nature-filled escape. Come pitch your tent and enjoy the serenity of the great outdoors-no charge for the stars!!
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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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$141.75

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Mobile Home

The Cupola

Roscoe, New York, United States

The Cupola is a restored 1965 Scotty Camper featuring cozy Tommy Bahama décor, mahogany finishes, and animal accents. Its private deck offers stunning pond and stream views. Sleeping two guests, a tent can be added for extra campers (see pricing). Amenities include a full bed, mini fridge, sink, propane cooktop, TV, firepit, and seating. On-site, enjoy a bath/shower, cold-water outhouse, and a commissary for last-minute needs. Firewood is available for purchase.
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View 22 Private vacation home

Home Most popular vacation rentals in Roscoe

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$222.59

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Private vacation home

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

Roscoe, New York, United States

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Sleep 6

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$324.68

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Cabin

Cozy Roscoe Lakefront Cabin

Roscoe, New York, United States

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Sleep 5

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$320.35

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Cabin

Secluded Mountain top

Roscoe, New York, United States

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Sleep 6

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$308.62

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Private vacation home

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

Roscoe, New York, United States

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Sleep 4

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$269.50

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Apartment

Cozy 2-bedroom apartment with Private River Access

Roscoe, New York, United States

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Sleep 6

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$265.84

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Cabin

Cozy Catskill Getaway with Airstream on a brook with fire pit. Pet friendly!

Roscoe, New York, United States

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$163.00

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Cabin

Woods I GO 2 Lose my Mind Roscoe

Roscoe, New York, United States

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$134.47

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Cabin

Property of Big Foot Roscoe, NY

Roscoe, New York, United States

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$140.06

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Cabin

Roscoe Coop Clucking Crazy Hut

Roscoe, New York, United States

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$1258.72

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Cabin

Stonewater Pines: Riverfront Property on 60 Acres

Roscoe, New York, United States

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