Explore Woodstock, Vermont from The Jackson Hotel – Walkable, Cozy, Scenic
If you’re planning a getaway to Woodstock, Vermont, look no further than The Jackson. Located just steps from the heart of downtown, The Jackson blends New England charm with modern convenience—making it one of the best places to stay in Woodstock, VT.
Stay Steps from Downtown Woodstock
Stay Steps from Downtown Woodstock
The Jackson sits less than a 5-minute walk from downtown Woodstock, where you’ll find:
- The iconic Middle Covered Bridge
- Local dining at spots like Mon Vert Café and Worthy Kitchen
- Artisan shops and historic general stores like F.H. Gillingham & Sons
- Seasonal events, art galleries, and live music on the Village Green
Woodstock is known for its walkable, welcoming feel—and when you stay at The Jackson, you’re right in the middle of it.
Close to Killington and Saskadena Six
Planning a ski weekend or outdoor adventure? The Jackson is located:
- 20 minutes from Killington Resort – Vermont’s largest ski and mountain biking destination
- 10 minutes from Saskadena Six – A family-friendly, local favorite for winter sports and year-round fun
- Minutes from hiking trails, covered bridges, and Marsh-Billings-Rockefeller National Historical Park
Whether you’re here for fall foliage, a summer hike, or a snowy ski escape, The Jackson puts you close to everything.
On-Site Dining at Oakes & Evelyn
Start your day with breakfast or unwind with dinner at Oakes & Evelyn, our on-site restaurant focused on locally sourced, seasonal fare. It’s one of Woodstock’s best-kept secrets for creative, comforting food—just steps from your room.
Cozy Rooms, Seamless Experience
What makes The Jackson different?
- Thoughtfully designed rooms with warm details and elevated finishes
- No formal check-in desk—skip the lines and go straight to your room
- A calm, relaxing environment perfect for couples, solo travelers, and weekend adventurers
We believe a great hotel should make your trip easier—not more complicated.
Why Guests Love Staying at The Jackson
- Walkable location in downtown Woodstock
- Easy access to Killington and Saskadena Six
- Cozy, design-forward rooms
- On-site restaurant with local flavor
- Direct-to-room check-in (no front desk required)
Whether you’re exploring covered bridges, hitting the slopes, or simply unwinding with a book by the window, The Jackson delivers the Vermont experience you’re looking for.
