Luxury 3300 sqft Ski and Golf Chalet, 4 Bedrooms & 4 En-suite Bathrooms, 2 Fireplaces & 1 Outdoor Fire pit, 5 min from Windham Mountain Club and 20 min from Hunter Mountain
Black Bear Cabin, Windham
Black Bear Cabin
Windham, NY, United States
Luxury 3300 sf. Bike/Hike/Golf Chalet. 4 bedrooms + 4 ensuite bathrooms. HotTub + Sauna + 2Fireplaces + fire pit. 5 min from Windham Mountain Club. 20 min from Hunter Mountain. Heated Pool (mid May- November) Heated outdoor dining patio with BBQ + Pizza oven. Cozy & spacious with southern exposure. Large eat-in chef's kitchen. Large dining area with fireplace. Spacious living room with fireplace. Large rec room + TV/Dolby bar, games, SONOS, poker and pool table, gym, Peloton bike. Baby Crib
Good to know
Nestled in the enchanting landscape of the Catskills, this luxurious 3,300 sqft ski and golf chalet offers unparalleled comfort and elegance: Charming Interiors: Four bedrooms, each with its own en-suite bathroom with all amenities (shampoo, conditioner, bath gel, soap, QTips and body lotion), offering ultimate comfort and privacy. Cozy Atmosphere: Two fireplaces, large living areas, and soaring ceilings that enhance the spacious feel. A/C: The bedrooms and the livingroom have newly installed (August 2025) window A/C units and there is one additional portable unit available for your convenience. Family Friendly: Perfect for families, this property has 2 cribs, one high chair and plates and utensils for children. Entertainment Galore: A recreation room equipped with sports and games including a pool table and Peloton bike, as well as 3 smart TVs with a Dolby bar system and HDMI for game consoles. Modern Chef’s Kitchen: Fully equipped with all the essentials and a wine fridge, promoting ease for any wine and cooking enthusiast. Dining Experience: Enjoy meals in a large dining area beside a roaring fireplace or step outside to the propane BBQ and a firepit perfect for stargazing. Additional Amenities: SONOS Music System in multiple rooms for immersive sound. Wine Cellar for storing your select wines. Complimentary wood for the two indoor fireplaces and the outdoor firepit Fitness and Relaxation: Exercise area with available equipment, ideal for maintaining wellness during your stay. Outdoor Features Stunning Views: Situated with direct views of Windham Mountain and southern exposure for maximum daylight. Entertainment Spaces: Expansive deck with Adirondack chairs, a picnic table for alfresco meals, and a private setting deck. Swimming Pool- 34 x 18 salt water, heated swimming pool. Available through October, unless extreme weather conditions. Hot Tub- 7 person sophisticated salt water SPA Barrel Sauna Convenient Location Close Proximity: Near renowned ski resorts with plentiful shopping, dining, and entertainment options in nearby villages. All-Season Activities: Ski, hike, bike, golf, or explore the trails and outdoor festivities thriving in all seasons. Security: All outdoor spaces, including hot tub and swimming pool areas are equipped with security cameras for your safety. Pre-Arrival Details Start your vacation with ease, as we offer in-home massages, a private chef service, and baby equipment like cribs and high chairs upon request. Late check-out: The check-out time at Black Bear Cabin is 11 am, which allows guests to enjoy the morning. However, if possible we do offer the option for you to extend check out to as late as 8 pm. Once booked, you will receive the information on how to request late check-out. Early Check-in: The check-in time at Black Bear Cabin is 4 pm. However, if possible we do offer the option for you to request check-in as early as 10 am, which allows you to enjoy the property for a full day. Once booked, you will receive the information on how to request early check-in. Experience the perfect blend of rustic charm and modern amenities at Black Bear Cabin—a retreat enveloped in natural beauty and ideal for friends and family to gather year-round. Note: All guests must adhere to house rules including no smoking, parties, or unauthorized visitors. Contact us for early check-in or extended stay options. Your host is available to ensure you have a pleasant visit. For bookings that fall over Thanksgiving, Christmas, and the New Year's eve we kindly ask a minimum of 7 nights stay. We do offer a discount for week long stays in general. Feel free to send me an inquiry with any questions. Please enjoy your stay and leave with cherished memories from this beautiful Catskills destination!
Other Details to Note
RENTAL RULES: The Primary Renter certifies that they are at least 30 years of age and will provide a valid government-issued photo ID. The Primary Renter will be present with the group during the entire Rental Term. Should the Primary Renter misrepresent the purpose of their stay or the number of occupants, they will be evicted immediately without refund. No third-party rentals allowed. If you are below the age of 30, please send us an inquiry, describing the group size and travel purpose for pre-approval. The Primary Renter and Occupants shall comply with the following rules: A. Smoking or vaping is not allowed inside the property. B. Do not tamper with the smoke detectors, carbon monoxide detectors or alarm system. C. No Fireworks of any kind are permitted on the Property, this includes sparklers. D. The Propane / Gas BBQ Grill is intended for outdoor use and shall not be moved from its outdoor patio location. The Grill is not part of the cleaning service. Please clean grill after using. E. Comply with any and all rules or regulations covering the Property including but not limited to local ordinances, health or safety codes. F. Dispose of any and all waste properly in accordance with Homeowner instructions. G. Do not obstruct any structure intended for ingress, egress, passage or otherwise providing access to, from or through the Property. H. Refrain from all activities that will cause unreasonable loud noises or otherwise unduly disturb neighbors and/or other residents. No parties or events are allowed at the property. Please be courteous to the neighboring homes and keep noise levels down late at night and early in the morning. I. Keep the Property and furnishings in good order. J. Only use appliances for their intended uses. K. Parking: Parking is limited to our driveway. Parking on the road is not permitted. Any illegally parked cars are subject to towing; applicable fines/towing fees are the sole responsibility of the vehicle owner. L. Housekeeping: There is no daily housekeeping service during your stay. While linens and bath towels are included in the unit, daily maid service is not included in the rental rate. M. Fireplace: The fireplaces are wood burning. You are responsible for following the guidelines located near each fireplace for preparing a safe fire including building an appropriate size fire. No more than 3-4 logs are permitted to be concurrently burned in a single fireplace. N. Toilet Usage: Do not flush anything other than toilet paper. No feminine products should be flushed at any time. If it is found that foreign materials or feminine products have been flushed, you shall be found liable for damages to plumbing and septic systems. O. No hunting or firearms are allowed on the Property. This includes BB, Airsoft, Bow, Compound Bow or any other similar type weapon. P. No illegal activities permitted on the Property. Pool, Hot Tub, and Sauna Rules: P. Use of Pool, Hot Tub, and Sauna is at Guest’s Own Risk. No lifeguard is on duty. Children must be supervised by an adult at all times when using these facilities. Q. No Glass or Breakable Items are permitted in or around the pool, hot tub, or sauna areas. Please use only non-breakable drinkware outdoors. R. Shower Before Use. Please rinse off before entering the pool, hot tub, or sauna to help maintain cleanliness and proper water chemistry. S. Hours of Use: Pool, hot tub, and sauna may be used only between 8:00 AM and 8:00 PM to ensure safety and respect for neighbors. Use outside of these hours is not permitted. T. Noise: No loud music, shouting, or disruptive behavior is permitted in the pool, hot tub, or sauna areas at any time. Please be respectful of our neighbors and keep noise to a minimum, especially in the evening. U. No Diving or Rough Play. Running, diving, or horseplay in or around the pool and hot tub is strictly prohibited. V. Cover and Secure After Use: Please securely cover the hot tub and pool when not in use to preserve heat, ensure safety, and protect from debris. W. No Food or Beverages in the Hot Tub or Sauna. These areas are for relaxation and health purposes only. Bringing food or drinks into the hot tub or sauna is strictly prohibited. X. Health Considerations: Do not use the hot tub or sauna if you are pregnant, have high blood pressure, heart conditions, or other serious health concerns unless cleared by a physician. Y. Proper Swimwear is Required. Nudity is not permitted in any outdoor areas of the property. Z. Outdoor Towels and Slippers: We have provided designated outdoor towels and slippers for your convenience, located near the entrance to the hot tub from the basement. Please use only these towels for outdoor activities. Bath towels must remain indoors to avoid unnecessary damage and wear. Do not walk indoors with wet slippers — the stone flooring can become extremely slippery and may cause accidents. AA. Outdoor Cameras: For your safety and the security of the property, exterior surveillance cameras are in place covering outdoor areas including the pool, hot tub, and sauna entry. There are no cameras inside the home or in any private interior areas. AB. Report Any Issues Immediately. If you notice any malfunction, damage, or safety concern with the pool, hot tub, or sauna, please notify us right away so we can address it promptly.
What this place offers
Common
- Air conditioning
- Cleaning products
- Cooking basics Pots and pans, oil, salt and pepper
- Dishes and silverware
- Dryer In the building, free or for a fee
- Essentials Towels, bed sheets, soap, toilet paper, and pillows
- Hair dryer
- Heating Central heating or a heater in the listing
- Hot tub
- Kitchen Space where guests can cook their own meals
- Dedicated workspace
- Pool
- TV
- Washing Machine
- Wifi
Luxury Amenities
- Air hockey table
- Golf course access
- Outdoor fireplace
- Security system
Outdoors
- Alfresco dining
- BBQ
- Fire pit
- Garden or backyard
- Hammock
- Outdoor seating
- Patio
- Sun loungers
What this place offers
Common
- Air conditioning
- Cleaning products
- Cooking basics Pots and pans, oil, salt and pepper
- Dishes and silverware
- Dryer In the building, free or for a fee
- Essentials Towels, bed sheets, soap, toilet paper, and pillows
- Hair dryer
- Heating Central heating or a heater in the listing
- Hot tub
- Kitchen Space where guests can cook their own meals
- Dedicated workspace
- Pool
- TV
- Washing Machine
- Wifi
Luxury Amenities
- Air hockey table
- Golf course access
- Outdoor fireplace
- Security system
Outdoors
- Alfresco dining
- BBQ
- Fire pit
- Garden or backyard
- Hammock
- Outdoor seating
- Patio
- Sun loungers
Kitchen and dining
- Baking sheet
- Barbecue utensils
- Blender
- Bread maker
- Coffee
- Coffee maker
- Dining table
- Dishwasher
- Freezer
- Hot water kettle
- Microwave
- Mini Fridge
- Oven
- Refrigerator
- Rice maker
- Stove
- Toaster
- Wine glasses
Bathroom
- Bathtub
- Bidet
- Body soap
- Conditioner
- Hot Water
- Shampoo
- Shower
- Shower gel
Bedroom and laundry
- Bed linens
- Drying rack for clothing
- Extra pillows and blankets
- Hangers
- Iron
- Mosquito net
- Room-darkening shades
- Clothing storage
Family
- Board games
- Changing table
- Children's books and toys
- Children's tableware
- Crib
- High chair
- Travel crib
Entertainment
- Books
- Exercise equipment
- Ping Pong Table
- Pool table
- Sound system
Home safety
- Carbon monoxide detector
- Fire extinguisher
- First aid kit
- Smoke detector
Heating and cooling
- Ceiling fan
- Indoor fireplace
- Portable fans
Parking and facilities
- Free parking on premises
- Gym
- Private living room
- Sauna
- Free street parking
Location features
- Garden view
- Mountain view
- Private entrance Separate street or building entrance
- Street view
Services
- Luggage dropoff allowed For guests' convenience when they have early arrival or late departure
Accessibility and Availability
Neighborhood
Nestled in the heart of the Catskills, this luxury chalet is surrounded by breathtaking landscapes and offers easy access to year-round outdoor activities. Enjoy skiing in the winter, hiking in the summer, and charming nearby villages filled with shopping and dining options for a complete getaway experience. refer to our local guide for our favorite and not be missed list of restaurants, shops and activities.
Guest Access
You will have access to the entire house except the shed and the owner closets.
Find us
Windham, NY, United States
Conveniently located just five minutes from Windham Mountain and twenty minutes from Hunter Mountain, and minutes away from various golf courses, the chalet is easily accessible by car, with ample parking available on-site. Public transport options are limited, so a private vehicle is recommended for exploring the beauty of the Catskills. We highly recommend having snow tires in the ski season.
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Approximate location. Full address will be provided on booking.