Summary:
Nestled on the edge of Woodstock, VT, The Homestead at Winterfound Farm stands as a beacon of history and charm, inviting guests to experience the essence of vintage Vermont. This long standing farmhouse, once a thriving moss farm, combines charm with the pastoral beauty of its surroundings.
Please SEE: Other Things to Note
For Area Details, Please SEE: The Neighborhood & Getting Around
*Pet Friendly, fee applies per pet.
*2027 Winter Seasonal Program - Ask How to Save 35%
The Space:
The Homestead at Winterfound Farm, Home Features:
• 5 Bedroom, 3 Bath - Available for up to 8 Guests!
• Well-Appointed Kitchen with All the Essentials
• Large Hearth Fireplace
• Experience the Rhythms of our Farm - Farm Animals!
• Free WiFi & Smart TVs
• Pack 'n play and/or high chair may be available upon request (subject to availability)
Step through the door and find yourself amidst sprawling acres of lush grass and open fields, the perfect prelude to miles of scenic trails winding through the verdant hillsides of Vermont. The property is also home to a natural pond and a working farm, where guests can enjoy the sights and sounds of farm life from a distance to appreciate its charm. This house was built in 1778. At around 250 years old, it is the oldest home in Barnard and a real working farm. While it has the quirks you'd expect from an authentic historic home, its character, warmth, and classic Vermont charm make it a truly special place to stay.
The main family room balances historical authenticity with modern comfort, featuring plush new furniture arranged to create a warm, inviting space for gatherings. The well-appointed kitchen is equipped with all essentials for preparing delightful meals, ideally enjoyed outdoors while admiring the expansive views of the countryside. Next to the kitchen, a quaint breakfast table for four offers a cozy nook by the woodstove, ideal for enjoying morning coffee and the picturesque outdoor scenery. Just a few steps out the backdoor leads to a large hot tub overlooking the backyard space.
Explore the rich heritage of each room on the first floor. The study houses a complete collection of National Geographic issues, while the den boasts a large hearth fireplace to warm up by after a day of outdoor adventures. The ground floor also hosts a master bedroom with a king-sized bed and abundant natural light, providing a tranquil retreat. Upstairs, the sleeping quarters feature four bedrooms and two bathrooms to accommodate various needs: two rooms with full beds, a bunk room with a full bed under a twin, and another bedroom with a full bed and plenty of storage space.
The property includes several farm structures that seamlessly integrate into the historic Vermont farmhouse scenery, further enhancing the authentic experience. At The Homestead at Winterfound Farm, every detail is carefully curated to ensure your stay captures the historical and natural beauty of Vermont. Book your visit and step into a picturesque world where history and modern comfort meet amidst the tranquility of Woodstock, VT. Revel in breathtaking views of the valley and our vibrant farm, enhanced by a suite of thoughtfully curated amenities. Experience the rhythms of our farm as you observe a variety of animals in their natural setting. You may even spot our on-site farmer tending to the land! Venture from your doorstep to discover extensive VAST trails that wander past our scenic pond—perfect for hiking, biking, and soaking in Vermont’s natural splendor.
For relaxation, unwind in our private covered hot tub or enjoy the serene waters of the pond. Winter brings the thrill of skiing, with our property conveniently located just a short drive from the premier ski resorts of Quechee, PICO, and Killington, and only minutes from Saskadena Six. Golf enthusiasts will find a paradise here, with many golf courses within a 50-mile radius, offering a variety of challenging layouts and stunning landscapes that cater to all skill levels. During the summer, bask in the picturesque beauty of our farm and the vibrant, changing foliage in autumn.
Our farmhouse marries rustic charm with modern amenities, providing you a unique opportunity to experience a tranquil countryside retreat unlike any other. This is a place where nature's beauty and homely comforts converge seamlessly, making every day a new opportunity for discovery and relaxation. Don’t miss your chance to enjoy a serene, high-end getaway at The Homestead at Winterfound Fields. Book your stay today and step into a world of adventure, relaxation, and golf in the heart of Vermont.
*2027 Winter Seasonal Program (Long-Term Reservations): Looking ahead to ski season? Make Vermont home for the season with Portoro Homes’ 2027 Winter Seasonal Program. It’s the perfect way to enjoy an extended stay near the mountains, cozy up for the season, and experience winter the right way. Designed for guests seeking a seamless extended stay in professionally managed homes across sought-after winter destinations. Plan ahead and save 35%. Reach out now to learn more about seasonal availability and details.
*Long Term Reservations: Guests booking reservations lasting 55 nights or more are responsible for and agree to pay all utilities which may include, but are not limited to: Propane, Oil, Electricity, Firewood, Trash Removal, and Snow Removal. These charges will be assessed within 60 days after check-out. Reservations with any dates between 1/4/27 and 3/6/27 must be 55 nights or more.
Guest Access:
We offer convenient door codes for self-check-in. Field and Farm by Portoro uses convenient keyless entry for self check-in, details provided 2 weeks (or less) prior to arrival by email and text message.
• Early check-ins or late check-outs: If the property happens to be ready earlier than the standard 3 pm check-in time on the day of your arrival, in most cases an early arrival option may be available when confirmed with the main office. Late check-outs must be confirmed with main office staff prior to the date of departure.
The Neighborhood:
Welcome to the enchanting Upper Valley, where Vermont's picturesque landscapes blend seamlessly with the cultural richness of Hanover, New Hampshire. Get ready to swoon over Woodstock, Vermont's charming hamlet. This historic village boasts stunning colonial and federal-style buildings that have been lovingly preserved for generations. It's the perfect spot for a dream vacation filled with architectural delights! Discover a collection of unique businesses that make this village extraordinary. From charming art galleries and quaint bookstores to specialty shops, cozy cafes, gourmet restaurants, and lively bars—there's always something delightful to explore! Beyond the allure of local activities, this property is set against one of New England's most stunning landscapes. Historical architecture and rolling hills combine to create a picturesque setting that captures the essence of Vermont's beauty. Located within 15 miles of three championship golf courses in Woodstock and Quechee.
Things to See & Do:
• Local Fun: horseback riding, hiking, fishing, skiing, golf & more!
• Ski: Saskadena Six Ski Hill, Killington Ski Resort, PICO Ski Resort
• Award-Winning Golf Courses: Woodstock Country Club, Quechee Lakes Country Club, Green Mountain National, Killington Mountain Course
• Explore: Mount Peg trail system, Hike Mount Tom, Historic Covered Bridge Tour, Billings Farm and Museum, Hike the Quechee Gorge “Vermont's Little Grand Canyon”, Visit the charming village of Quechee, take in the views of the Ottauquechee River
• Museums: Billings Farm & Museum, Hood Museum of Art, Montshire Museum
• Local Markets: Gillingham's, Woodstock Farmers Market, Feast and Field Market, Mac’s Market
• Local Restaurants & Shopping
- Restaurants: The Prince & The Pauper Restaurant, Worthy Kitchen, Mon Vert Café, Simon Pearce Restaurant, Cloudland Farm, Kelly Way Gardens, Village Butcher, Dr. Coburn's Tonic
- Shops: Sudie’s, VT Flannel Co., Woodstock Sports, Yankee Bookstore, Red Wagon Toy Company, Farmhouse Pottery, Simon Pearce
Annual Festivals & Events:
• Woodstock Apples and Crafts Fair and food truck festival
• Covered Bridges Half Marathon
• Feast and Field
• Taste of Woodstock
• Quechee Hot Air Balloon, Craft & Music Festival
• Wassail Weekend
• Woodstock Apples and Crafts Fair and food truck festival
• Woodstock Art Festival
• Hunter Jumper Show
We provide a full list of Things to Do & See and local Restaurants & Shops to experience for our guests including in a personalized Guest Manual in your check-in details provided prior to your stay!
Village of Woodstock Rental Registration Number #
Interaction with Guests:
Our goal is that your vacation exceed your expectations. Field and Farm by Portoro communicates via email and phone. After a booking is confirmed, rental agreement will be emailed to the guest for e-signature. Check-in instructions are sent by email and text message 14 days (or less) prior to arrival date. We offer convenient keyless entry for self-check in. We do typically check in with guests by text 1-2 times during their stays to ensure a 5-star experience and remain available for any questions. We are available to guests 24/7 for any inquiries.
