The Bearsville Barn is a beautifully restored 1889 gem—featured in Vogue and “Woodstock Handmade Houses—located just 8 minutes from the heart of Woodstock. The one-of-a-kind property embraces the property’s original character with upgraded touches including a fully-fenced in-ground pool, 12-foot movie screen projector, chef’s kitchen, and outdoor pizza oven. The home includes two private bedrooms and two expansive lofted sleeping quarters. You will be situated at the foothills of the Catskills with limitless opportunities to explore the Hudson Valley!


You can rest easy knowing your stay is covered with $1,500 in “All-Risk” Damage Protection. Although rare, accidental damage from guests does happen. Traditionally, this was managed via a security deposit or vacation rental damage insurance purchased by the guest. Both are cumbersome and often have big limitations in protection.

With “all-risk” protection, all accidental damage from a guest is covered unless specifically excluded such as, but not limited to, normal wear and tear, infestation, or prior damage.
We hope you enjoy your vacation with peace of mind knowing that if an accident happens and damages occur, you are protected under Waivo.

Home Sweet Hudson is a proud member of VRMA, an international Vacation Rental Management Association. Our mission as a professional management company is to foster professionalism, collaboration, and growth for short-term rentals in our area. We hope you will help us support our mission by abiding by all of our house rules, supporting our local community, and being respectful of the home during your time in the beautiful Hudson Valley.

- Routinely scheduled maintenance by Home Sweet Hudson team members or lawn care/snow plowing may happen during your stay. This also includes garbage pick up, linen pickup, hot tub service, and pool cleanings.
- This is not a pet-friendly property.
- The pool is available from Memorial Day weekend to Labor Day weekend. It is not heated*
- Parking shall be allowed solely in the designated parking spaces
- Smoking is not permitted anywhere on the premises.
- Weapons are strictly prohibited
- Please adhere to safety instructions for fireplaces, firepits, etc.
- Due to the risk of fire, please do not charge your electric car on the property.
- We do not allow parties or extra guests outside the maximum occupancy allowed on the reservation. We also ask you to follow the good neighbor guidelines and abide by quiet hours after 9 pm.
- Please do not trespass on property boundaries
- Tents, yurts, and other camping equipment are prohibited
- This house does not have a backup generator

This property is managed by Home Sweet Hudson, a trusted & local management company. Our team is passionate about connecting with each guest and providing unique stay places for your Hudson Valley vacation! We’re here to help answer any questions and provide thoughtful support throughout your trip.

Home Sweet Hudson has partnered with local third-party vendors who offer amazing add-on features to your stay. The Hudson Valley is a beautiful area to relax and rejuvenate, and now you can do it from the comfort of your ‘home’!

Private Yoga Classes: Bring the studio vibes to you, and enjoy a tailored private yoga class.

In-Home Private Chef’s: Skip the shopping and experience fine dining with locally sourced ingredients, seasonal menus and delicious wine pairings.

Private Massage Session: Whether you’ve been hiking, skiing or just taking in the views, an in home massage is the perfect way to unwind on your vacation.

Interested in learning more? Be sure to message us with what services you’d like to explore so we can check availability and help coordinate your experience!


The property includes a variety of areas to enjoy and is generally split into two main sections: The Barn and The Cabin.

THE BARN:
Guests enter the home through The Barn and upon arriving you'll instantly be taken by the massive open space with a wall of windows looking out onto your own private back garden. The ceilings stretch 30 feet tall and feature original wood beams from 1889—from its former life as a sheep and hay barn.

This main space includes a full living room with sofas, chairs, a wood stove, and a piano as well as a Carrera and Zinc wet bar (with dishwasher) and a 12-foot wood dining table perfect for serving big dinners.

The Barn also features a private bedroom with a Queen bed, an open lofted bedroom (semi-private) with a sitting area including a dresser and a TV, and a full bathroom on the main floor.

THE CABIN:
As you pass through the barn, you’ll find a door leading to what was once a separate cabin which now contains the master bedroom, kitchen, a full bathroom, and another lofted bedroom (semi-private). Note: The loft over the kitchen is less private than the barn loft but it’s still a great place to wake up and take in nature through your own large picture window.

KITCHEN
The kitchen is truly built for a chef, with a 6-burner commercial gas stove & oven, a kitchen island, espresso machine (with bean grinder), drip-coffee maker, breakfast table and all of the pots and pans you'll need to make a great meal!

SLEEPING SPACE
Bedrooms include:
● Primary Bedroom: King bed
● Guest Room 1: Full/Double bed
● The Barn Loft: Full/Double bed
● The Cabin Loft: Full/Double bed
● 1 crib available

BATHROOMS
There are two full bathrooms each with a tub and one with a shower.
Toiletries are available in both bathrooms and a washer and dryer, as well as pool towels, are located on the main level for your convenience.

OUTDOOR LIVING SPACE
There is a newly restored pool with beautiful outdoor furniture, an outdoor shower, and pool toys for the kids. A large table is available for eating under the stars or in the sunshine—complete with an umbrella for some shade.
Around the back is the outdoor kitchen, lovingly built complete with a pizza oven, wood grill, and smoker. Perfect for summer entertainment!