Why The Jackson Is the Perfect Home Base for Your Woodstock, Vermont Getaway
Tucked in the heart of Vermont, Woodstock is the kind of town that feels straight out of a postcard—covered bridges, cozy cafes, mountain views, and a pace that encourages you to slow down. And when it comes to where to stay in Woodstock, The Jackson offers a timeless experience that’s as charming as the town itself.
Whether you’re here for leaf-peeping, skiing at Killington, or just a quiet weekend escape, The Jackson puts you within walking distance of it all.
Walkable, Relaxed, and Full of Charm
Located just steps from downtown Woodstock, The Jackson is a 16-room hotel that blends thoughtful design with small-town warmth. Our rooms are individually styled, our check-in is fully contactless, and our local recommendations come from real people who live and breathe Vermont.
You’ll be close to:
Downtown shops and restaurants
The Ottauquechee River and Middle Covered Bridge
Marsh-Billings-Rockefeller National Historical Park
Killington and Six Ski Areas
Endless trails, farms, and hidden gems
The Jackson Experience
We believe staying in a hotel should feel easy—and maybe even a little exciting. That’s why we offer:
- Direct-to-room check-in (no front desk, no lines)
- Cozy, design-forward rooms that feel like a retreat
- On-site dining at Oakes & Evelyn, serving up breakfast daily and creative New England fare for dinner Thursday–Sunday
- Locally curated recommendations so you can explore like a regular, not a tourist
Woodstock, Vermont: A Year-Round Destination
No matter the season, Woodstock delivers:
- Fall: Foliage hikes, farm stands, and scenic drives
- Winter: Skiing, snowshoeing, and cozy après-ski vibes
- Spring: Maple tapping, art galleries, and quiet weekends
- Summer: Swimming holes, farmers markets, and long walks downtown
Whether you’re planning a romantic weekend, a family escape, or a solo recharge, The Jackson is your effortless entry point to one of Vermont’s most beloved towns.
