Escape to a private luxury retreat in the Catskills—designed for families and groups seeking space, privacy, and meaningful time together.This 3,300 sq. ft. chalet features 4 ensuite bedrooms, a heated pool (May–Nov), hot tub, sauna, and sweeping mountain views. Just 5 minutes from Windham Mountain, it offers the perfect balance of nature, comfort, and elevated design.Whether you're planning a weekend escape, ski trip, or special gathering, Black Bear Cabin is where lasting memories are made.A Private Retreat Designed for ConnectionWelcome to Black Bear Cabin—a refined mountain escape where architecture, nature, and comfort come together effortlessly.Set against direct views of Windham Mountain, this 3,300 sq. ft. chalet was designed for those who value privacy, space, and a seamless group experience.From the moment you arrive, every detail invites you to slow down, reconnect, and fully enjoy your time together.Space & Privacy Without CompromiseFour bedrooms, each with its own private ensuite bathroomExpansive layout ideal for families, multi-family stays, and retreatsThoughtfully designed to balance togetherness and personal spaceElevated LivingThe main living space features vaulted wood-paneled ceilings, a grand stone fireplace, and a dramatic arched window framing the mountain.It’s a place to gather after a day outdoors—whether for conversation, quiet moments, or simply enjoying the view.Designed for Gathering and HostingFully equipped chef’s kitchen with wine fridgeLarge dining area with fireplaceOutdoor dining patio with BBQ and pizza ovenPerfect for long dinners, shared meals, and effortless entertaining.Entertainment, Seamlessly Built InDedicated recreation room with pool table, poker, and gamesSmart TVs with Dolby sound + SONOS throughoutPeloton and fitness areaEverything is designed so your group never needs to leave to enjoy the experience.Wellness & RelaxationHeated saltwater pool (mid-May through November, weather permitting)7-person hot tubBarrel saunaA private, spa-like setting to unwind in every season.Thoughtfully Family-ReadyCribs, high chair, and children’s essentialsSpacious layout ideal for families traveling togetherSafe, private outdoor environmentThe property is professionally treated to help minimize tick exposure and maintained with preventative measures; however, as with any natural setting, we cannot guarantee a tick-free environment and encourage appropriate precautions during your stay.Outdoor LivingExpansive deck with Adirondack seatingFire pit for evenings under the starsSouthern exposure for natural light throughout the dayUnobstructed mountain viewsPrime Location5 minutes to Windham Mountain Club20 minutes to Hunter MountainClose to hiking, golf, dining, and year-round outdoor activitiesOptional Elevated ServicesEnhance your stay with curated add-ons available upon request:Private chef experiencesIn-home massagePrivate Yoga sessionsSki and winter activity packagesPre-arrival arrangements The ExperienceBlack Bear Cabin is more than a place to stay—it’s a setting designed for connection, celebration, and time well spent.Guest accessGuests enjoy full private access to the entire 3,300 sq. ft. property, including all indoor and outdoor spaces—pool, hot tub, sauna, decks, and recreation areas.Self check-in via secure smart lockNo shared spacesA small number of owner closets and the outdoor shed remain locked for maintenance purposesInteraction with guestsYour stay is designed to feel effortless and private.We offer seamless self check-in and will not be present at the property during your stay. However, we are always available and responsive via the app or phone for anything you may need—from recommendations to assistance—ensuring a smooth and enjoyable experience from start to finish.Other details to noteProperty & SafetyExterior security cameras are installed in outdoor areas (including driveway and pool/hot tub zones) for safety and property monitoringThere are no cameras inside the homeCheck-In & Check-OutCheck-in: 4:00 PMCheck-out: 11:00 AMEarly check-in / late check-out may be available for an additional fee upon request after bookingHouse StandardsTo maintain the quality and experience of the home:No parties or eventsNo smoking or vaping anywhere on the propertyRegistered guests only; no unauthorized visitorsQuiet hours must be respected, especially in the eveningThese standards are strictly enforced to ensure a peaceful environment for all guests and neighbors.Booking RequirementsPrimary renter must be 30+ years oldThe booking guest must be present for the duration of the stayPool, Hot Tub & SaunaUse is at your own risk; children must be supervised at all timesNo glassware permitted in outdoor wellness areasUsage hours apply to ensure safety and respect for neighborsHousekeepingFresh linens and towels are provided at arrivalDaily housekeeping is not includedGuest ServicesOptional services available upon request:Private chefIn-home massageAdditional baby equipmentHoliday BookingsA 7-night minimum applies for Thanksgiving, Christmas, and New Year’s staysDiscounts available for extended staysBooking & House GuidelinesTo ensure a smooth and high-quality experience for all guests, we follow a simple pre-arrival process.After booking, guests will receive a brief summary of house guidelines and be asked to complete a standard rental agreement and provide a valid photo ID for verification.This is a quick and secure step, typical for professionally managed homes, and helps us maintain the quality, safety, and privacy of the experience for everyone.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:In order for the booking to not be cancelled, guests must sign the lease agreement sent to them upon booking on VRBO, within 24 hours of receiving it..The primary renter must be at least 30 years old and provide a copy of government issued ID with the signed lease.,If you are below the age of 30, please send us an inquiry describing your group and the purpose of travel for pre-approval..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 30.About events:No events allowed.