venue and property details

Couples often tell us that the weekend – not just the day – was the part they’ll always remember. Built in 1792, Weatherhead Hollow is a thoughtfully restored Vermont farmstead offering a balance of historic character and modern comfort, located just 10 minutes from the town of Brattleboro, Vermont.

The property sleeps up to twelve guests across the 1792 Farmhouse and Carriage Barn. The Farmhouse includes three bedrooms, three full bathrooms (two with clawfoot tubs), a formal dining room, colorful kitchen, a large patio with fire pit, and multiple lounge spaces designed for gathering and connection. The Carriage Barn features two bedrooms, one full bathroom with soaking tub, and a well appointed kitchen. Both accommodations have earned 5-star reviews from more than 250 Airbnb guests, which you can explore on our country getaway page.

For events, couples celebrate in our restored Bank Barn – a rare Vermont design built into the hillside – featuring a central event hall with adjoining corn crib bar overlooking the barnyard. The barn comfortably accommodates up to 150 guests for a seated dinner, with space for a dance floor, live band or DJ, and buffet setup. Outdoor ceremonies are popular, with options beneath a 200-year-old maple tree or within the barnyard. The barn is ADA accessible.

Weatherhead Hollow is conveniently located 10 minutes from Brattleboro, Vermont, approximately two hours from Albany, New York, two and a half hours from Boston, and three and a half hours from New York City. Bradley International Airport in Connecticut is about a 1 hour and 15 minute drive.

Wedding Weekend Package

Ideal for couples seeking a full wedding weekend celebration with a guest list of up to 150 guests. This package is designed to give you time, space, and flexibility to host multiple moments with your guests over several days.

The Wedding Weekend Package includes:

• Historic Barn + Farmstead

  • Ceremony beneath an ancient maple tree or within the barn

  • Barn reception with chandeliers, lanterns, and twinkling lights

  • Rehearsal dinner and farewell brunch

  • Full access to the barn event spaces and farmstead grounds

    • Celebrations planned to wrap by 10:00 PM, with a midnight celebration extension available by request.

• Three nights of on-site accommodation for up to 12 guests

  • The Farmhouse

  • The Carriage Barn

• Property management support, including vendor guidance and table layout coordination

• Convenient on-site guest parking

• Use of select authentic farmstead décor items

Couples have the freedom to shape their weekend in a way that feels right to them — from simple and DIY to fully curated — and select their vendor team accordingly, from catering and bar service to rentals and florals, using our trusted vendor list or their own preferred professionals.

Optional add-ons include:

• Midnight Celebration & Late Check-Out (limited availability)

• Additional nights in the Farmhouse and Carriage Barn

• Early check-in or late check-out (based on availability; late check-out included with midnight celebration extension)

• Setup and clean-up service

• Nearby accommodations within walking distance, booked separately through our neighbors, include:

  • The Blacksmith Shop (hosts 4 guests)

  • The Schoolhouse (hosts 6 guests)

  • Maple Ridge Farm (a private campground in the mountains that hosts ~35 guests)

The fine print: This package includes a minimum three-night stay with exclusive access to the farmstead during your visit. Longer stays may be available on request.

An event planner or coordinator is required to ensure a smooth and joyful experience. We are happy to suggest trusted professionals, or you’re welcome to bring your own.

A 50% retainer + refundable security deposit are required to secure the venue. Add-on services may be selected up to six weeks in advance of the reservation, based on availability.

We’ve worked closely with the State of Vermont and Town of Guilford to host events in a way that respects community regulations and local guidelines.

Looking for more detail?

Below you’ll find additional resources to help you imagine your weekend at Weatherhead Hollow — from décor and floor plans to vendor guidance and frequently asked questions.

Many couples find the FAQ especially helpful as they begin planning.

If you feel ready to inquire or schedule a tour, you’re welcome to reach out through our Book Now page.