Entire Farm! The Homestead & Barn at Winterfound

Summary:

Book both homes on Winterfound Farm for the ultimate Vermont getaway! With 8 bedrooms and 5 bathrooms across two beautifully distinct properties, this buyout sleeps up to 16 guests — perfect for family reunions, group retreats, and celebrations.



THE HOMESTEAD (5BR/3BA): A historic 1778 farmhouse with a large hearth fireplace, wood stove, and panoramic valley views. Well-appointed kitchen, cozy den, and study. Private hot tub overlooking the backyard.



THE BARN (3BR/2BA): A beautifully renovated barn with a chef's dream kitchen, open-concept living, and a private covered hot tub with stunning valley views.



Both properties share the sprawling Winterfound Farm — a working farm with animals, a scenic pond, and miles of VAST trails right outside your door. Minutes from Saskadena Six, Killington, and PICO ski resorts. 10 minutes from the charming village of Woodstock.



Please SEE: Other Things to Note

For Area Details, Please SEE: The Neighborhood & Getting Around

*No pets allowed for buyout bookings.

*2027 Winter Seasonal Program - Ask How to Save 35%



The Space:

Winterfound Farm Buyout — 8 Bedrooms, 5 Baths, Sleeps 16



THE HOMESTEAD AT WINTERFOUND FARM (481 South Perry Road):

• 5 Bedrooms, 3 Bathrooms — Sleeps 8

• Historic 1778 farmhouse — the oldest home in Barnard

• Well-appointed kitchen with all essentials

• Large hearth fireplace in the den, wood stove in the breakfast nook

• Study with complete National Geographic collection

• Ground floor king master bedroom with en-suite bath

• Four upstairs bedrooms: two full beds, one bunk room (full under twin), one full bed

• Private hot tub overlooking the backyard

• Free WiFi & Smart TVs

• Pack 'n play and/or high chair available upon request



THE BARN AT WINTERFOUND FARM (456 South Perry Road):

• 3 Bedrooms, 2 Bathrooms — Sleeps 8

• Beautifully renovated barn with stunning valley views

• Open-concept gourmet kitchen, dining, and living area

• King primary bedroom on upper level with en-suite soaking tub

• First floor: bunk room (full under twin + trundle, sleeps 4) and queen room

• Private covered hot tub with valley views

• Free WiFi & Smart TVs



SHARED FARM EXPERIENCE:

• Working farm with animals — observe from a respectful distance

• Scenic pond and miles of VAST trails for hiking, biking, and exploring

• Minutes from Saskadena Six, Killington, PICO, and Quechee ski resorts

• Located within 15 miles of three championship golf courses

• 10 minutes from the charming village of Woodstock, VT



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.



This buyout includes two separate buildings, each with its own entry:

• THE HOMESTEAD (481 S Perry Rd): Door code entry at the front door.

• THE BARN (456 S Perry Rd): Door code entry.



• We cannot guarantee early check-ins or late check-outs, as both are subject to availability. Please contact us 24 hours prior to check-in to submit your request.



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 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 #



Getting Around:

Come and make unforgettable memories in this charming Vermont haven. We welcome you! This Upper Valley experience seamlessly weaves together the natural beauty of Vermont with the cultural vibrancy of Hanover, creating an unforgettable blend of outdoor adventures, historical exploration, and small-town charm.



Traveling to/around the Upper Valley region of Vermont - Explore by foot, by ski, by bike, or by horseback:

• You'll definitely need your own car, as there are limited taxis available. While the town itself is walkable, it will be necessary to drive to nearby hikes and sightseeing spots.

• Bike rentals are available in the village.



Airports:

• Burlington (BTV) [VT]

• Lebanon (LEB) [NH]

• Manchester (MHT) [NH]

• Boston Logan (BOS) [MA]



Popular Landmarks:

• Mount Ascutney

• Norman Williams Public Library

• Woodstock Town Hall

• Marsh Billings Rockefeller Historical Site

• The New England Falconry

• President Calvin Coolidge State Historic Site

• Sugarbush Farm

• Hanover, home to Dartmouth University



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.



• We cannot guarantee early check-ins or late check-outs, as both are subject to availability. Please contact us 24 hours prior to check-in to submit your request.



Note: This buyout listing includes two separate buildings — The Homestead and The Barn. Each has its own door code and check-in details, which will be provided prior to arrival.