Top Vermont Towns for a Cozy Winter Getaway
When winter descends upon Vermont, the state transforms into a snowy wonderland that invites travelers to bask in the warmth of a cozy cabin, enjoy the thrill of outdoor adventures, and explore charming small towns brimming with character. There’s no better way to experience winter than with a stay in Vermont’s top towns, where comfort meets classic New England charm. Whether you're looking to hit the slopes, sip hot cocoa by a crackling fire, or discover local artisans’ wares, these Vermont towns are perfect for your next winter escape.
1. Stowe: The Quintessential Winter Wonderland
Stowe is synonymous with winter in Vermont. Known as the “Ski Capital of the East,” it boasts world-class skiing and snowboarding at Stowe Mountain Resort. But Stowe is more than just a ski destination—it’s a picturesque town where you can explore boutique shops, enjoy farm-to-table dining, and unwind in luxury accommodations that feature cozy fireplaces and mountain views. For non-skiers, there’s plenty to do: try ice skating, take a scenic sleigh ride, or enjoy the scenic Stowe Recreation Path blanketed in snow.
Book this Stowe cabin to enjoy the charm of the area.
2. Woodstock: Vermont’s Timeless Treasure
Woodstock is the epitome of New England charm. With its covered bridges, historic architecture, and welcoming community spirit, Woodstock is perfect for a peaceful winter getaway. Visit Billings Farm & Museum to learn about the region’s agricultural history or stroll down Main Street, which is adorned with twinkling lights during the holiday season. For winter sports enthusiasts, the nearby Saskadena Ski Area offers gentle slopes ideal for families and beginners.
Book a Woodstock home with a stellar view.
3. Killington: The Adventurer’s Paradise
For those who crave adrenaline and a bustling après-ski scene, Killington is the place to be. Home to the largest ski area in the Eastern U.S., Killington Resort, this town offers extensive trails for skiers and snowboarders of all levels. Off the slopes, enjoy snowmobiling, snowshoeing, or cozying up at one of the many slope-side pubs. The energy in Killington during winter is unmatched, making it perfect for those who seek excitement.
Book this storybook cottage just a scenic drive away from the slopes.
4. Bennington: A Blend of History and Scenic Beauty
Located in southern Vermont, Bennington is known for its rich history, beautiful mountain views, and a welcoming atmosphere. Explore the Bennington Battle Monument, stroll through the town’s vibrant arts district, or take a scenic drive to admire snow-capped mountains and covered bridges. The nearby Green Mountain National Forest offers trails perfect for winter hiking and snowshoeing.
Stay at a historic village home in Bennington Vermont.
5. Manchester: Luxury Meets Tradition
Nestled in southern Vermont, Manchester is where luxury and tradition seamlessly blend. Known for its designer outlets and upscale dining, Manchester is also home to Bromley Mountain and Stratton Mountain, offering great skiing options. This town’s charm comes from its combination of outdoor recreation, cultural attractions like the Southern Vermont Arts Center, Southern Vermont Arts Center and elegant vacation rentals equipped with modern amenities.
Find the perfect Manchester vacation rental for a weekend getaway.
6. Woodstock: A Cozy, Classic Retreat
For those who appreciate history, charm, and scenic beauty, Woodstock is the perfect winter destination. The town's picturesque streets are lined with 19th-century buildings, artisan shops, and inviting cafes. Take a snowy stroll across its famous covered bridges or explore the serene trails for cross-country skiing and snowshoeing. Woodstock's vibrant community and tranquil ambiance make it a standout for winter relaxation.
Find a cabin in Woodstock this winter.
Explore more Vermont vacation rentals and start planning your winter getaway!
Vermont's own vacation rental site, Stayclass, features unique stays you won’t find anywhere else—all booking fee-free. Plan your perfect winter escape and support local hosts while making lasting memories.