Chalet
Bear Hollow - 10 mins to Kingston! MONTHLY RATES!
Photo gallery for Bear Hollow - 10 mins to Kingston! MONTHLY RATES!





3 bedrooms3 bathroomsSleeps 6250.8 sq m
Popular amenities
Explore the area

Mount Tremper, New York
- Emerson Place Kaleidoscope13 min drive
- Catskill Mountains19 min drive
- Overlook Mountain Trailhead26 min drive
Rooms & beds
3 bedrooms (sleeps 6)
Bedroom 1
1 King Bed
Bedroom 2
1 Queen Bed
Bedroom 3
1 Queen Bed
Living Room 1
2 Single Bunk Beds
3 bathrooms
Bathroom 1
Bathtub · Toilet · Shower only
Bathroom 2
Toilet · Shower only
Bathroom 3
Toilet · Shower only
Spaces
Deck or patio
Kitchen
Office
Balcony
Garden
Dining area
About this property
Bear Hollow - 10 mins to Kingston! MONTHLY RATES!
Summary:
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)
The Space:
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.
Guest Access:
The bunk beds on the lower level are not in an enclosed room. The sleeping area is set up in the open floor family/TV room and is ideally suited for children. This sleeping area accommodates up to 4 children.
The maximum occupancy of this home is 6 adults, plus 4 children.
The Neighborhood:
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.
Getting Around:
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.
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)
The Space:
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.
Guest Access:
The bunk beds on the lower level are not in an enclosed room. The sleeping area is set up in the open floor family/TV room and is ideally suited for children. This sleeping area accommodates up to 4 children.
The maximum occupancy of this home is 6 adults, plus 4 children.
The Neighborhood:
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.
Getting Around:
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.
Property manager
Red Cottage
Add dates for prices
Amenities
Kitchen
Washer
Dryer
Pet-friendly
Air conditioning
Outdoor space
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House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
Pets allowed
Charge may apply
Smoking
Smoking is not permitted
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
About the area
Mount Tremper
Located in Mount Tremper, this chalet is in a rural area and in the mountains. Emerson Place Kaleidoscope and Overlook Mountain Trailhead are local landmarks, and the area's natural beauty can be seen at Catskill Mountains and Catskill State Park. Empire State Railway Museum and Woodstock Music Shop are also worth visiting. Spend some time exploring the area's activities, including snowboarding.

Mount Tremper, New York
What's nearby
- Mount Tremper Arts - 11 min drive - 7.3 km
- Emerson Place Kaleidoscope - 13 min drive - 9.5 km
- Catskill Mountains - 19 min drive - 11.8 km
- Overlook Mountain Trailhead - 26 min drive - 18.2 km
- Hunter Mountain - 39 min drive - 36.1 km
Getting around
Restaurants
- Olive's Country Store & Cafe - 19 min drive
- Phoenicia Diner - 15 min drive
- Colony - 19 min drive
- Bread Alone - 19 min drive
- Good Night - 19 min drive
Frequently asked questions
Reviews
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About the host
Hosted by Red Cottage

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