Where to Stay in Bennington, VT | Hotels, Inns & More
Cozy up for a night or weekend at these Bennington, VT, hotels and inns. And while you’re there, check out some of our picks for where to eat and what to do.
Taraden Bed & Breakfast | Guide to Bennington, Vermont
Photo Credit : Courtesy of Taraden Bed & Breakfast
Southern Vermont doesn’t always get the love that the state’s northern half does, and that’s a shame. Outdoor adventure, history, and small-town charm give this region the kind of New England character that visitors to the Northeast crave. Consider Bennington, the largest small town in southern Vermont. It’s divided into three distinct areas — Old Bennington, North Bennington, and downtown — and each one is worth exploring. Discovering all the terrific Bennington, VT, hotels, restaurants, covered bridges, waterfalls, and shopping makes the town a fine place to spend a weekend.
Of course, history runs deep in Bennington, too. This is Ethan Allen and Green Mountain Boys turf, and, lest we forget, the Bennington Battle Monument points a solemn finger skyward, marking a Revolutionary War victory. And it’s fitting that the only museum dedicated to the preservation of covered bridges found a home at Bennington’s Center for the Arts, now known as the Laumeister Art Center at Southern Vermont College. Plus, if you like a taste of the old world, you should know that Yankee named Bennington one of the “Best Antique Towns in New England.”
Ready for a visit? Read on for our selection of the best Bennington, VT, hotels and inns, as well as some other favorite stops.
Downtown Bennington | Best Bennington, VT, Hotels & Inns Photo Credit : Lynn Green/Four Chimneys Inn
This gem of a B&B offers more activity packages than many larger establishments do. Tailor your stay around cross-country skiing, cycling, horseback riding, spa pampering, and wine-pairing dinners at an acclaimed nearby restaurant. Named a 2014 Yankee Editors’ Pick for “Best Small B&B.”
Taraden Bed & Breakfast | Best Bennington, VT, Hotels & Inns Photo Credit : Courtesy of Taraden Bed & Breakfast
Nestled on 20 acres overlooking the Taconic Range and the Green Mountains, Taraden offers spacious suites with private baths, including one in a separate cottage. Enjoy pond and pasture views from the glassed-in breakfast room, and then climb aboard a horse-drawn carriage for a scenic tour. Named a 2015 Yankee Editors’ Pick for “Best Mountain Vistas.”
The Four Chimneys Inn | Best Bennington, VT, Hotels & Inns Photo Credit : Courtesy of The Four Chimneys Inn/Lynn Green
Set on an 18th-century property, the Four Chimneys Inn has been a local landmark since the 1950s, when it was a fine-dining restaurant whose guests included Richard Burton, Elizabeth Taylor, and Walt Disney. (Local lore claims that Norman Rockwell painted a scene in the main dining room, though the work has never been found.) Now a restored B&B, Four Chimneys has positioned itself as a romantic getaway, with amenities that include in-room flowers and champagne. Stays include a complimentary country breakfast.
Room options run the gamut at this downtown establishment, from a simple economy to the King Sauna (yep, it’s got a real sauna) to the King Studio Suite (living room, kitchenette, and pullout couch). It’s located within easy reach of Bennington’s attractions as well as many of southern Vermont’s outdoor draws, including Mount Snow, Stratton, and Killington.
An old-world ambience defines this B&B and its nine guest rooms. Dinner and theater packages include two nights and two tickets to a performance at Oldcastle Theatre and dinner or lunch at Bennington Station Restaurant.
And while you’re visiting Bennington, don’t forget to explore these other Yankee favorite stops…
Hans Krijnen began his baking career more than 30 years ago in Holland, learning to make the pastries and breads that are today the hallmark of the Bennington bakery he owns with his wife, Jennifer. Along the way he also learned to make delicious cakes, cookies, and croissants. Named a 2014 Yankee Editors’ Pick for “Best Danish.”
A slice of New York City can be found at this North Bennington restaurant, where the menu includes rack of lamb with mint pistachio pesto, tomato chutney, and roasted carrots and roasted Long Island duck breast over saffron risotto and Burgundy cherry sauce.
What do folk artist Grandma Moses and abstract artist Helen Frankenthaler have in common? How about a 1920s Martin Wasp automobile and works by contemporary sculptor Sir Anthony Caro? They’re examples of this museum’s varied and rich collection, which juxtapose traditional with modern. Named a 2015 Yankee Editors’ Pick for “Best Museum Makeover.”
While the stately marble building at Bennington’s downtown crossroads still looks like a bank, today it overflows not with cash but rather with carefully selected glassware, ceramics, jewelry, paintings, and fiber works from throughout North America. Take a break from browsing to play a few free games on a vintage pinball machine, pound out a tune on the 1936 baby grand piano, or unleash the kids’ imaginations with chalk and blackboards in the Graffiti Vault, once the bank’s walk-in safe. Named a 2017 Yankee Editors’ Pick for “Best Craft Gallery.”
Sprawled throughout two 18th-century barns, the 25,000-square-foot Antique Center showcases the wares of more than 200 dealers. Named a 2012 Yankee Editors’ Pick for “Best Rummaging.”
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