Where to Stay in Woodstock, Vermont: The Jackson Hotel
Looking for the perfect place to stay in Woodstock, Vermont? Nestled just steps from the heart of downtown, The Jackson offers cozy, design-forward rooms with modern convenience—right in the middle of everything that makes Woodstock one of New England’s most beloved towns.
Whether you’re planning a fall foliage road trip, a ski weekend at Killington, or a quiet couples’ getaway, The Jackson in Woodstock, VT is your ideal home base.
Unbeatable Location in Downtown Woodstock, Vermont
The Jackson is located less than a 5-minute walk from the shops, restaurants, and galleries of downtown Woodstock, Vermont. That means easy access to:
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Middle Covered Bridge
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Local favorites like Mon Vert Café and Worthy Kitchen
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F.H. Gillingham & Sons (a must-visit general store)
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Boutique shopping and weekend farmer’s markets
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Art galleries and cultural events on the Village Green
Unlike larger resorts or remote rentals, The Jackson puts you in the center of it all—no car needed.
Close to Killington, Saskadena Six & Outdoor Adventures
Planning to ski or hike while visiting? The Jackson is just 20 minutes from Killington Resort, one of the top ski destinations in the Northeast. We’re also minutes from Saskadena Six and near popular trailheads for hiking, biking, and snowshoeing.
Guests at The Jackson can explore:
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Killington Mountain (skiing, snowboarding, summer mountain biking)
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Saskadena Six (family-friendly skiing and local favorite)
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Mount Tom and Marsh-Billings-Rockefeller National Historical Park
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Ottauquechee River swimming and paddling
Whether it’s a winter ski trip or summer escape, The Jackson offers the best of Vermont’s outdoors—right outside your door.
On-Site Dining at Oakes & Evelyn
Start your day with breakfast and wind down with dinner just steps from your room at Oakes & Evelyn, The Jackson’s on-site restaurant. With a focus on locally sourced, seasonal ingredients, it’s one of Woodstock’s hidden gems for creative, delicious food.
Thoughtful Comfort, Seamless Stays
Every room at The Jackson is designed with comfort in mind—from cozy bedding to in-room conveniences. And with our direct-to-room check-in (no front desk required), your stay is smooth and stress-free.
Why Stay at The Jackson in Woodstock, VT?
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Prime location near downtown Woodstock
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Easy access to Killington Resort and Saskadena Six
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Walkable to restaurants, shops, and historic landmarks
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On-site restaurant: Oakes & Evelyn
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Direct-to-room check-in with no hassle
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Cozy, modern rooms with New England charm
