Entire home
Chic two Cottage compound with pool and hot tub in a pastoral Woodstock setting.
Photo gallery for Chic two Cottage compound with pool and hot tub in a pastoral Woodstock setting.





Reviews
10 out of 10
Exceptional
4 bedrooms 2 bathrooms Sleeps 4 185.8 sq m
Popular amenities
Explore the area

Bearsville, NY
- Woodstock Music Shop5 min drive
- Overlook Mountain Trailhead11 min drive
- Karma Triyana Dharmachakra Monastery11 min drive
- Hudson, NY (HCC-Columbia County)60 min drive
Rooms & beds
4 bedrooms (sleeps 4)
Bedroom Guest House
1 King Bed
Guest bedroom main house
2 Single Beds
Living room guest house
1 Double Sofa Bed
Main Bedroom main house
1 Queen Bed
2 bathrooms
Bathroom guest house
Soap · Towels provided · Bathtub or shower · Toilet · Shampoo
Bathroom main house
Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shower only · Shampoo · Hair dryer
Spaces
Deck or patio
Porch or lanai
Kitchen
Separate dining area
Outdoor play area
Garden
Dining area
About this property
Chic two Cottage compound with pool and hot tub in a pastoral Woodstock setting.
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, 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!
Add dates for prices
Amenities
Pool
Hot tub
Kitchen
Washing machine
Dryer
Pet-friendly
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House Rules
Check in after 3:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
No more than 8 people total including the guests
Pets
Pets allowed: dogs (limit 1 total)
Please message me to get permission first
Smoking
Smoking is not permitted
Check-out instructions
The host requires you to complete the following before checking out:
Load and start the dishwasher
Strip any used beds
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights and lock the doors
Please remember to cover any outdoor furniture
Please turn the AC/mini splits off in the summer and set the heat to 60 degrees in the winter
Failure to complete these may result in a negative review from the host.
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
Note from host: no more than 8 people total including the guests
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 and a first aid kit
Property Registration Number 23H-068
We should mention
A car is recommended for transport to and from this property
About the area
Bearsville
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, while those wishing to experience the area's natural beauty can explore Catskill Mountains. Travelling with kids? Consider Empire State Railway Museum, or check out an event or a game at Dietz Stadium. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

Bearsville, NY
What's nearby
- Woodstock Music Shop - 5 min drive - 4.4 km
- Byrdcliffe Barn - 5 min drive - 4.6 km
- Woodstock Golf Club - 6 min drive - 5.1 km
- Overlook Mountain Trailhead - 11 min drive - 7.5 km
- Karma Triyana Dharmachakra Monastery - 11 min drive - 7.5 km
Getting around
Restaurants
- Good Night - 4 min drive
- Colony - 4 min drive
- Caffe Woodstock - 5 min drive
- Bread Alone Bakery - 4 min drive
- Cumberland Farms - 5 min drive
Frequently asked questions
About the host
Hosted by Erica O'Neill

A painter who has long loved the Woodstock area.
Why they chose this property
Charm Charm Charm, Built by the neighboring farmer's family in 1930 for an emigre family from Germany. It has a woodsy feel with charming little details. When we first saw it it was the setting that grabbed us, it's not grand but super relaxed and now a little lux with the new bathrooms and kitchens and the addition of the new hot tub and heated saline pool. The Hamlet of Bearsville has green hills and dark starry nights.
Come and rejuvenate yourself in the relaxing compound, set in landscaped grounds surrounded by flowering apple and magnolia trees.
Come and rejuvenate yourself in the relaxing compound, set in landscaped grounds surrounded by flowering apple and magnolia trees.
What makes this property unique
You are in the country with all delicious benefits, from the farm next door where you can walk over in the morning and buy your happy eggs, to outdoorsy activities like swimming holes, hiking, tubing & trout fishing, yet close to everything you would need to have a relaxing time, with art galleries, Zagat rated restaurants, a cute little village for a stroll and some shopping and the relaxed atmosphere of a cosmopolitan environment in this historic arts community walkable to cocktails at the Bearsville Cafe compound.
Languages:
English
Premier Host
They consistently provide great experiences for their guests
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