Woodstock Trail Cottage | 2 Blocks from the Inn

Summary:

Woodstock Trail Cottage puts you steps from the Mt. Peg trailhead and an easy walk from the shops, dining, and charm of Woodstock Village. Come home to a cozy, light-filled cape with hardwood floors, an easy open layout, and a covered back porch with seating overlooking the perennial gardens, perfect for coffee, conversation, and four-season Vermont views.



Please see: Other Things to Note

For Area Details, please see: The Neighborhood & Getting Around

• This is a no pet/animal home.



The Space:

Woodstock Trail Cottage, Home Features:

• 3 Bedrooms, 2 Baths, up to 6 guests

• Steps To Mt. Peg Trailhead

• Walk To Woodstock Village & The Green

• Covered Back Porch With Seating

• Open Kitchen With Dining Area + First Floor Laundry

• Free WiFi & Smart TV



Sleeping Arrangements:

• Multi-Level Home

• Bedroom 1, Queen Bed (1st Floor)

• Bedroom 2, Queen Bed (2nd Floor)

• Bedroom 3, 2 twins (2nd Floor)



Welcome to Woodstock Trail Cottage!



Tucked on a quiet dead-end street in the heart of Woodstock Village, this charming circa-1880 Cape pairs walk-to-town convenience with a private covered back porch that quickly becomes everyone's favorite spot. Set directly across from the Mt. Peg trailhead, it's easy to start the morning with a hike, then stroll into town for coffee, shopping, and the year-round events on the Historic Woodstock Green. Championship golf, fly fishing, and skiing are all close by, making this a true four-season home base.

Inside, the cottage blends antique character with an easy, comfortable layout. Hardwood floors run throughout, and the open kitchen anchors the main level with a bright, welcoming flow into the dining area and adjacent sitting space, ideal for lingering breakfasts, shared meals, and relaxed evenings in. A first-floor bedroom pairs with a nearby bath featuring soothing green accents, and the convenience of first-floor laundry makes longer stays feel effortless.



Upstairs, the home continues with two additional bedrooms filled with natural light, along with a sweet library nook that's perfect for curling up with a book on a rainy day. A second bathroom on this level helps the home live comfortably for groups, with space that suits couples traveling together, families, or friends looking for a classic Woodstock getaway.



Out back, the covered porch is the kind of space you'll use from the moment you arrive. From the seating area, you look out over the private yard and perennial gardens, with trees framing the view and a calm, tucked-away feel that's hard to find this close to the village. It's perfect for morning coffee while the light comes up, après-ski conversations as the day winds down, or a quiet hour with a book while you watch the seasons change. The porch is set up for real lounging and easy gathering, with comfortable seating that turns it into an "extra room" in warm months and a front-row seat to snowfall in winter.



Woodstock Trail Cottage delivers a rare combination of village convenience, trail access, and timeless Vermont charm.



Guest Access:

This home uses keyless entry for self-check-in; your door code is sent by email and text within two weeks of arrival. Early check-in and late check-out are available upon request (subject to availability). Please contact us at least 24 hours in advance.



NOTE: The property is best accessed from the back covered porch and instructions are provided in guest check-in details.



The Neighborhood:

Welcome to Woodstock, Vermont, where storybook village charm meets fresh-air adventure at the doorstep. Set on a quiet dead-end street in the heart of Woodstock Village, 13 Golf Avenue sits directly across from the Mt. Peg trailhead, making it effortless to start your day with a hike and end it with a stroll to the Historic Woodstock Green. This beloved village is known for its beautifully preserved architecture, inviting boutiques, galleries, and bookstores, plus cozy cafés and standout restaurants that make wandering around town part of the vacation. Beyond the village, the landscape is pure Vermont—rolling hills, winding roads, and four-season beauty that feels like a postcard in every direction. With golf, fly fishing, and skiing all nearby, this is an ideal home base for a classic New England getaway.



Things to See & Do:

• Explore: Hike Mt. Peg From The Trailhead Across The Street, Stroll The Historic Woodstock Green, Visit Billings Farm & Museum, Walk The Village Shops And Galleries

• Covered Bridge Tours: Taftsville Covered Bridge, Quechee Covered Bridge, Middle Covered Bridge

• Ski: Saskadena Six Ski Area, Killington Ski Resort, Pico Mountain

• Award-Winning Golf Courses: Woodstock Country Club, Quechee Lakes Country Club, Green Mountain National Golf Course, Killington Mountain Course

• Museums: Billings Farm & Museum, Woodstock History Center, Vermont Institute Of Natural Science, Montshire Museum Of Science, Simon Pearce Mill

• Local Markets: Woodstock Farmers’ Market

• Local Restaurants & Shopping

Restaurants: Simon Pearce, The Skinny Pancake, Worthy Kitchen, Prince & The Pauper

Shops: F. H. Gillingham & Sons, Woodstock Scoops, Local Boutiques And Galleries Around The Green



Annual Festivals & Events:

• Wassail Weekend In Woodstock

• Quechee Hot Air Balloon, Craft & Music Festival

• Vermont State Fair



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 nearby Hanover, creating an unforgettable blend of outdoor adventure, historical exploration, and small-town charm. Whether you’re soaking in the scenic wonders, browsing village shops, or planning a day trip to Dartmouth, the Upper Valley promises a little something for every traveler. From Woodstock to Barnard and beyond, you’ll find endless opportunities for hiking, skiing, biking, and relaxed afternoons that feel quintessentially New England.



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 village itself is walkable, it will be necessary to drive to nearby hikes and sightseeing spots. The outer parts of town, such as South Woodstock, are only conveniently accessed by car.

• Bike rentals are available in the village, though biking in the commercial area is discouraged, as the flow of people and cars can be concentrated. The terrain has many hills, and a mountain bike should be used to traverse more rugged areas.



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 National Historical Park

• Saint-Gaudens National Historic Site

• President Calvin Coolidge State Historic Site

• Alden Partridge Plaque

• Joseph Smith Memorial

• Whale’s Dance

• Largest Zipper in North America

• Vermont Vietnam Veteran’s Memorial

• Hanover, Home to Dartmouth University



Interaction with Guests:

Our goal is that your vacation exceed your expectations. Field & Farm Vacation Homes 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 follow the CDC and Airbnb Recommended Cleaning Guidelines. You can rest assured this property has been completely sanitized prior to check-in.



• 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.