Where you’ll sleep
Experience modern chalet living with mountain views, just minutes from Woodstock and a short drive from NYC.
- –Stylish chalet on 5 private acres with stunning mountain views, offering a tranquil Catskills escape.
- –Perfect blend of modern comfort and natural beauty, just 10 minutes from vibrant Woodstock.
- –Flexible sleeping arrangements and dedicated family spaces make it ideal for multi-generational getaways.
Welcome to Bear Hollow, a spacious and modern chalet-style home with mountain views and stylish interiors—just 10 minutes to Woodstock and 2. 5 hrs from NYC!
About this property
Welcome to Bear Hollow, a spacious and modern chalet-style home with mountain views and stylish interiors—just 10 minutes to Woodstock and 2.5 hrs from NYC!
Sitting on 5 serene acres, this 3 bed, 3 bath home perfectly accommodates 6 adults, (*and up to 10 including children*) Enjoy bright and airy interiors, a cozy wood-stove, elevated deck, family/TV room, guest bedrooms with deck access & an upper-level primary suite.
Nearby towns: Woodstock (10 mins), Phoenicia (16 mins)
Inside, the open-plan main floor boasts natural wood floors with high ceilings, large windows and glass sliding doors that flood the space with natural light. The living room invites you to unwind and relax on the large sectional sofa next to the cozy woodstove, and the glass doors lead out onto the elevated deck where outdoor dining and grilling is highlighted by the picturesque backdrop of scenic mountain vistas. The well-equipped kitchen includes a breakfast bar and is open to the living/dining area, creating an effortless flow for entertaining and enjoying meals together.
The two guest bedrooms on the main floor provide restful retreats, each offering queen beds and glass doors that open directly onto the deck—ideal for savoring your morning coffee or enjoying a breath of fresh air. The two guest bedrooms share a beautifully appointed bathroom with a shower and tub combo. Encompassing the entire upper level, the spacious primary suite offers additional privacy, featuring a king bed with warm wood accents, a skylight perfect for stargazing at night, a dedicated workspace, and an elegant ensuite bathroom.
Venture downstairs to discover a sprawling family room outfitted with plush sofas and a large TV, ideal for movie nights or relaxing after outdoor adventures. A sleeping area set up with 2 bunk beds is perfect for families with kids, and features another convenient workspace. On this level, a third full bathroom and laundry facilities are available for added convenience.
Outside, immerse yourself in the tranquil ambiance of the expansive property, where sweeping mountain views, inviting outdoor seating, a relaxing hammock, and lawn games create the perfect setting for relaxation and enjoyment.
Bear Hollow offers a beautiful and relaxing accommodation in a superb location, nestled amidst the natural beauty of the Hudson Valley and Catskills. Perfect for families and friends alike seeking a tranquil retreat with easy access to outdoor adventures and local attractions.
The area
Discover Mount Tremper, where summer unfolds with hiking trails through Wilson State Park's serene landscapes. Only 10 minutes from Woodstock Village and Boiceville, enjoy local dining, artisanal shops, and vibrant community events. Delight in farm-to-table cuisine and bustling farmers markets, or relax with tubing and fly fishing on Esopus Creek in nearby Phoenicia.
In winter, nearby ski resorts offer thrilling slopes and snowboarding. Embrace the season with cozy craft breweries and wineries amidst scenic vistas. Cultural festivals like the Festival of the Voice and Woodstock Film Festival add artistic charm to this picturesque Catskills destination. Experience seamless outdoor thrills and cultural richness in Mount Tremper, the perfect escape to the Hudson Valley/Catskills.
Bear Hollow is just 2.5 hours from New York City, and you'll definitely want a car to get there and around the area. In the winter, we recommend a car with four-wheel drive that can handle the snow and gravel roads.
Notes from your host
Cooling: There is one split unit that cools the main floor and a portable AC unit in the upstairs bedroom
full description, the area, host notes
Managed by Red Cottage
New York, NY
2,925 reviews
Red Cottage is a vacation rental management company offering curated Catskills, Hudson Valley, Berkshires and Northeast properties with guest services and multi-platform listings.








