Weatherhead Hollow Farmstead – Two historic homes on a private Vermont property

Weatherhead Hollow is a private Vermont farmstead with two historic homes — the 1792 Farmhouse and the Carriage Barn — reserved together as one thoughtfully designed property. Surrounded by rolling fields, ancient apple trees, and mountain views of the hollow, the farmstead invites a slower rhythm, with space to gather, rest, and enjoy time together. This listing is ideal for extended families, close friends, or small reunions seeking comfort, privacy, and a sense of place — all within easy access of Brattleboro and southern Vermont.

The farmstead sleeps up to 12 overnight guests across two separate buildings. The 1792 Farmhouse comfortably hosts up to 8 guests with three bedrooms, three full bathrooms, multiple gathering spaces, and a fenced yard. The Carriage Barn hosts up to 4 guests in a cozy two-bedroom layout with an open-concept living space and private side yard. Together, the property offers space to be together while still allowing room to spread out.

THE 1792 FARMHOUSE
The Farmhouse is a two-story historic home, thoughtfully renovated to include modern comforts while preserving the character of the original 1792 structure. Inside, the house unfolds into several inviting sitting rooms, allowing guests to gather together or enjoy quiet moments apart. With exposed beams, hardwood floors, colorful wallpaper and art, and bespoke furnishings throughout, the Farmhouse is equally well-suited to a relaxed group stay or a slower, restorative retreat.

The Farmhouse includes three private bedrooms and three full bathrooms, including two clawfoot soaking tubs.

The Primary Bedroom Suite (upstairs) features a king-size bed with a luxury firm Saatva mattress, a large walk-through closet, and an ensuite bathroom with a clawfoot tub and separate walk-in shower — perfect for long soaks. The walk-through closet also serves as the Farmhouse laundry room, with a high-efficiency washer and dryer, steamer, iron, and extra linens.

The Upstairs Queen Bedroom includes a queen-size luxury firm Saatva mattress, dresser, closet, and charming “witches stairs” leading to a small loft. The loft is not recommended for sleeping. A nearby full bathroom features a red-tiled shower and soapstone sink.

The Finished Basement Bedroom is located in a finished portion of the basement, accessed by a staircase with a handrail. This bright and colorful space includes a queen-size bed with a Green Tea memory foam mattress and a sitting area with a full-size fold-out sofa bed. A HEPA air purifier helps keep airflow fresh. This room also includes a TV set up for DVDs and VHS.

Downstairs living spaces include:
– A large farmhouse kitchen with gas stove and dishwasher
– A breakfast nook and entertainment lounge with a Vizio V-Series 50" 4K Smart TV and record player, plus a record collection
– Dining room seating for 10
– A living room and sun room
– A full bathroom with clawfoot tub

WiFi is strong throughout the house and on the front porch. Verizon cell service is limited.

The Farmhouse outdoor space includes a fully fenced backyard with an outdoor dining table, fire pit, charcoal grill, and views of the surrounding fields and mountains — ideal for lingering evenings and relaxed mornings.

THE CARRIAGE BARN
The Carriage Barn is a historic two-story cottage, fully renovated to balance original character with colorful, comfortable design. With exposed beams, dormer windows, and knotty pine floors, it offers a cozy counterpoint to the larger Farmhouse and works best as a peaceful sleeping space for part of the group.

The Carriage Barn includes two bedrooms and one full bathroom.

The Queen Bedroom features a plush Saatva mattress, writing desk, rocking chair, and closets.

The Guest Bedroom includes two full-size antique beds with luxury firm mattresses, a large dresser, and original barn board wall details.

The bathroom features a charming clawfoot tub and shower tucked into a dormer window.

Upstairs, the Carriage Barn includes an open-concept living space with:
– A petite but well-equipped kitchen (best suited for one or two people cooking at a time)
– Comfortable dining and lounge area with a Vizio V-Series 43" 4K Smart TV and DVD set up
– Washer and dryer are located on the lower level near the entry
– Bedrooms are located on opposite ends of the barn with shared living spaces in between

Carriage Barn guests enjoy a private side yard with a bistro table beneath two maple trees — a quiet place to read, relax, or enjoy a morning coffee.

ADDITIONAL NOTES
– The Farmhouse and Carriage Barn share a loop gravel driveway but have separate entrances and outdoor spaces. Most groups naturally gather in the Farmhouse and its fenced backyard.
– Both buildings have their own washer and dryer.
– WiFi is strong throughout both homes; Verizon cell service is limited.
– This is a historic property and is not child-proofed – you won’t find outlet plugs, corner guards, or similar safety modifications. In the Carriage Barn, a gate is available at the top of the stairs. In the Farmhouse, doors from each room open onto stairways and can be closed. Children are welcome with active parental supervision.
– Dogs are welcome by prior inclusion on the reservation (maximum two). The fenced backyard enclosure is approximately 3.5 feet high; dogs prone to jumping should be supervised.
– The owners work out of the large barn on the far side of the farmstead – you will have complete privacy and may check in without us present, but we are nearby and available if needed during your stay. Our gentle and well-socialized dog Bartleby spends time outdoors within a wireless boundary system and may occasionally greet guests in shared outdoor areas such as the parking area. If you or your dog are uncomfortable around dogs, the farmstead may not be the best fit for your stay.
– The farmstead includes one first-floor bathroom. There are no first-floor bedrooms, and both houses require at least one interior step and the use of a staircase with railings to access sleeping areas.
– The property is supplied by filtered country well water that is safe to drink. As is common in rural Vermont, guests may occasionally notice a mild natural mineral scent at certain times of year due to seasonal groundwater fluctuations.
– This listing is for lodging only and is not suitable for events, parties, wedding preparations, photography sessions, or transportation staging without prior written approval.

LOCATION
Weatherhead Hollow is located just 10 minutes from Brattleboro, Vermont, with easy access via paved roads year-round. The property is approximately 45 minutes from Mount Snow and about an hour from several other southern Vermont ski areas. Weatherhead Hollow Road is a quiet, scenic country road popular for walking, biking, and running, and the Guilford Country Store is a short drive away.

Weatherhead Hollow is owned and cared for by experienced hosts who restore and steward historic properties with a focus on thoughtful design, careful upkeep, and attentive hosting. The Farmhouse and Carriage Barn interiors have been featured in AtHome New England Magazine and in the book Create the Style You Crave: The Sweet Spot Guide to Home Decor for their elegant, playful design.

When not hosting guests, Weatherhead Hollow supports Vermont’s creative economy through fully funded artist residencies. Original artwork and handmade pieces are woven throughout the Farmhouse and Carriage Barn — many created during these residencies, and all sourced from working artists rather than mass-market décor. It’s one of the ways the property remains authentic and deeply connected to the creative community.