Updated on Jul 20, 2026
|
Type
|
Cottage
|
|
Bedrooms
|
4
|
|
Bathrooms
|
2
|
|
House Rules
|
-
Pets allowed: dogs (limit 1 total);Please message me to get permission first
-
Children allowed: ages 0-17
-
Smoking is not permitted
-
No events allowed;No more than 8 people total including the guests
|
|
Max Occupancy
|
8
|
|
Host Language
|
English
|
|
Property Id
|
472316
|
The Bearsville Retreat is a secluded bucolic compound nestled in the trees of Bearsville, a quarter mile from the gourmet marketplace The Cub and the historic Bearsville Theater, and just two miles (5 min drive) to Woodstock's town center. The property consists of two charming cottages, freestanding office, heated saltwater pool (there is an additional fee to heat the pool), luxurious hot tub, fire pit, and a children's play structure. Pastoral and mountain views abound. Come relax, recharge, and enjoy the natural beauty of the Catskills.
Located in Bearsville, a hamlet of Woodstock, the serene two-acre property is tucked away from the road, with beautiful mountain views, providing a postcard-perfect backdrop to wake up to every morning, while also close to everything. Spend your afternoons swimming in the heated saltwater pool, relax in the hot tub, or lounge in a hammock in the apple orchard while the kids swing and play in the club house. Pass your evenings barbecuing and dining alfresco on the bluestone patio, playing charades in the game room, or roasting marshmallows in the fire pit. Located within the historic township of Woodstock, with it’s charming boutiques, farm-to-table restaurants, and rich history of music and art, The Bearsville Retreat is the perfect spot to enjoy all that the Catskills have to offer.
THE MAIN HOUSE has two bedrooms: The primary bedroom has a queen bed, and the second bedroom has two twin beds — both bedrooms are cozy and comfortable with designer furniture, premium bedding, and new skylights. The brand-new kitchen is fully stocked with microwave, coffee maker, and everything you need to cook for family or guests. The bathroom features both walk-in shower and deep soaking tub — a relaxing treat at the end of a long day of hiking or skiing. The stylishly-decorated living room has a wood burning fireplace and plenty of comfy seating, Apple TV, bluetooth stereo/record player, and wifi that extends across the property. The game room, which is stocked with board games, puzzles, art books and an antique chess/backgammon table, leads out to a sunny bluestone patio with a twelve-person al fresco dining table and barbecue. The wood-paneled dining room is a cozy space with the feel of an old fashioned captain's stateroom, an ideal spot for both quiet breakfasts and lively dinner parties.
THE GUEST HOUSE features open floor plan with a loft-like, sun-filled living room with a wall of windows facing onto the pool. There is wifi throughout the house, as well as a smart TV/Blue ray and record player. There is a mini library filled with books and DVDs which can be enjoyed on the sofa in front of the pot-bellied stove. The chef’s kitchen is fully equipped with new appliances, a marble-topped island, and plenty of counter space for preparing meals. The spacious dining area comfortably seats six. The bedroom has a luxurious king sized bed with upholstered headboard, and plenty of natural light from windows facing out to the pool. The bathroom features a deep soaking tub and skylight, perfect for relaxing and looking up at the stars. The sofa in the living room converts into a queen bed for extra sleeping space (please let us know ahead of time if you want this bed made up before you arrive).
THE GROUNDS' beautifully maintained sprawling lawns are picturesque. The 20' X 40' heated saltwater pool (additional heating fee), outdoor shower, and brand new hot tub are privately situated in the back yard, while the front yard features an apple orchard, pastural views of the historic neighboring farm, a fire pit, and a 'Brad's Barns Expedition' children's swing-set, with play structure, and club house.
THE OFFICE is a freestanding building located behind the main house. It is equipped with a desk, plush couch, and hardwired ethernet. It is private and comfortable, making work away from home a breeze.
See you soon!
Located in Bearsville, this cottage is in a rural area. Hunter Mountain and Kaaterskill Falls are worth checking out if an activity is on the agenda. Traveling with kids? Consider Empire State Railway Museum, or check out an event or a game at Dietz Stadium. Enjoy the area's slopes with cross-country skiing and snowboarding, and don't miss out on the sledding and snowmobiling.
Get the full listing »
1 Br Cottage Vacation Rental In Bearsville, New York - Vrbo Property # 2542085
This is a luxurious newly-renovated 1 BR, 1 bath, modern guest cottage privately sited away from the main house. It has concrete radiant floors throughout, 3-season room, dedicated WiFi, fire pit...
4 Br Lodge Vacation Rental In Ellenville, New York - Vrbo Property # 2738430
Your Catskills Escape: Rustic-Modern Comfort, Family-Friendly, Nature-InspiredStep into a serene retreat where every detail is designed for relaxation, wellness, and adventure. Perfect for a family...
3 Br Private Vacation Home Vacation Rental In Bearsville, New York - Vrbo Property # 990567
The Woodstock House is distinctive and gracious.The Woodstock house is ideally located within walking distance to the Bear Cafe, Little Bear restaurant, Cub Market, and the Bearsville Theater. It...
4 Br Private Vacation Home Vacation Rental In Elka Park, New York - Vrbo Property # 4667749
Relax and unwind in this light-filled 4-bedroom house, complete with wraparound deck and huge yard.The newly renovated main house features two rooms with king beds, one with an en-suite bathroom...
2 Br Cabin Vacation Rental In Boiceville, New York - Vrbo Property # 4190457
Winston's Place is a cozy cabin nestled into a wooded backdrop, in the Catskill Mountains. Quiet dead end road, large wrap around deck, walking distance to the Esopus Creek. The cabin, built in...
4 Br Private Vacation Home Vacation Rental In Bearsville, New York - Vrbo Property # 4545094
This home in the Shady hamlet of Woodstock, less than 10 minutes from Town, is the perfect Retreat. There are 4 bedrooms, 2 1/2 baths, a heated pool in summer, and a hot tub year-round. The common...
2 Br Private Vacation Home Vacation Rental In Chichester, New York - Vrbo Property # 2948909
Forget your worries in this tranquil cottage, located on Catskill Mountains. This furnished 2-bedroom home is the ideal place for those who have an appreciation of solitude and nature. The cottage...
2 Br Private Vacation Home Vacation Rental In Shady, New York - Vrbo Property # 132977
3 -30 day minimum depending on season. Discount with 7 days.+ Surrounded by the forests of Mt. Guardian at an altitude of 1500 feet. + Large summer porch overlooks a beautiful pond + AC +...
3 Br Private Vacation Home Vacation Rental In Accord, New York - Vrbo Property # 3044795
Relax in privacy and peace. Tucked in beautiful Accord with wonderful spots to enjoy just nearby: Arrowood Brewery & Distillery. Westwind Cidery. Inness Resort and Golf Course. Saunderskill Farms....
4 Br Cabin Vacation Rental In Bearsville, New York - Vrbo Property # 245959
Our well-equipped cabin sits at the end of a dead-end road on three secluded acres including rolling lawn, woodlands, and a pretty pond. You probably won't hear another car all weekend. Yet we are...