4 Br Chalet Vacation Rental In Windham, New York

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 Connection
Welcome 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 Compromise
Four bedrooms, each with its own private ensuite bathroom
Expansive layout ideal for families, multi-family stays, and retreats
Thoughtfully designed to balance togetherness and personal space

Elevated Living
The 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 Hosting
Fully equipped chef’s kitchen with wine fridge
Large dining area with fireplace
Outdoor dining patio with BBQ and pizza oven

Perfect for long dinners, shared meals, and effortless entertaining.

Entertainment, Seamlessly Built In
Dedicated recreation room with pool table, poker, and games
Smart TVs with Dolby sound + SONOS throughout
Peloton and fitness area

Everything is designed so your group never needs to leave to enjoy the experience.

Wellness & Relaxation
Heated saltwater pool (mid-May through November, weather permitting)
7-person hot tub
Barrel sauna

A private, spa-like setting to unwind in every season.

Thoughtfully Family-Ready
Cribs, high chair, and children’s essentials
Spacious layout ideal for families traveling together
Safe, private outdoor environment

The 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 Living
Expansive deck with Adirondack seating
Fire pit for evenings under the stars
Southern exposure for natural light throughout the day
Unobstructed mountain views

Prime Location
5 minutes to Windham Mountain Club
20 minutes to Hunter Mountain
Close to hiking, golf, dining, and year-round outdoor activities

Optional Elevated Services
Enhance your stay with curated add-ons available upon request:

Private chef experiences
In-home massage
Private Yoga sessions
Ski and winter activity packages
Pre-arrival arrangements

The Experience
Black Bear Cabin is more than a place to stay—it’s a setting designed for connection, celebration, and time well spent.

Guest access
Guests 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 lock
No shared spaces
A small number of owner closets and the outdoor shed remain locked for maintenance purposes

Interaction with guests
Your 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 note

Property & Safety
Exterior security cameras are installed in outdoor areas (including driveway and pool/hot tub zones) for safety and property monitoring
There are no cameras inside the home

Check-In & Check-Out
Check-in: 4:00 PM
Check-out: 11:00 AM
Early check-in / late check-out may be available for an additional fee upon request after booking

House Standards
To maintain the quality and experience of the home:

No parties or events
No smoking or vaping anywhere on the property
Registered guests only; no unauthorized visitors
Quiet hours must be respected, especially in the evening

These standards are strictly enforced to ensure a peaceful environment for all guests and neighbors.

Booking Requirements
Primary renter must be 30+ years old
The booking guest must be present for the duration of the stay

Pool, Hot Tub & Sauna
Use is at your own risk; children must be supervised at all times
No glassware permitted in outdoor wellness areas
Usage hours apply to ensure safety and respect for neighbors

Housekeeping
Fresh linens and towels are provided at arrival
Daily housekeeping is not included

Guest Services
Optional services available upon request:

Private chef
In-home massage
Additional baby equipment

Holiday Bookings
A 7-night minimum applies for Thanksgiving, Christmas, and New Year’s stays
Discounts available for extended stays

Booking & House Guidelines
To 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.

Located in Windham, this chalet is in the city center and next to a golf course. Windham Mountain Resort and Hunter Mountain are worth checking out if an activity is on the agenda. Traveling with kids? Consider Zoom Flume and Mountain Top Arboretum. Take in the nearby slopes with cross-country skiing and snowboarding, or check out other outdoor activities such as sledding and snowmobiling.