The Most Beautiful Towns in Vermont, USA

Vermont's famous Sleepy Hollow Farm in Woodstock
Vermont's famous Sleepy Hollow Farm in Woodstock | © Cavan Images / Alamy Stock Photo
Photo of Rachel Gould
Art & Design Editor5 January 2021

Located in the USA’s northeastern New England region, Vermont is well known for its stunning natural beauty and quaint colonial towns. Take a look at our list of the most beautiful towns and villages to visit across Vermont.


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USA, New England, Vermont, Chester, town view
Chester | © Hemis / Alamy Stock Photo

Windsor County’s town of Chester is best known for its Stone Village and Chester Village Historic Districts, both of which are listed in the National Register of Historic Places. Stone Village got its name for the predominance of granite houses, and Chester Village features a typically New England federal and colonial aesthetic. A popular tourist destination for its character, Chester is home to the Chester Fall Festival in September, charming inns, antique shops, galleries and great restaurants. Additionally, Chester caters for cyclists, boaters and skiers, lying with driving distance of Okemo, Mount Snow and Killington.

Where to stay: Breathe in the fresh air at this idyllic cabin house retreat just outside Chester. Housing up to eight guests, it’s comfortable, private and provides easy access to the New England countryside.


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Dorset, Vermont, in autumn
Dorset | © Susan Pease / Alamy Stock Photo

The quiet and charming town of Dorset lies amid the hills of Bennington County in southern Vermont. Chartered in 1761, Dorset was the site of Cephas Kent’s famous tavern, which hosted meetings that eventually led to Vermont’s statehood. Dorset is also the location of America’s oldest marble quarry, which provided stone for the town’s sidewalks and the marble church next to the village green, as well as the main branch of the New York Public Library. Take a swim in the quarry, partake in the Dorset Theatre Festival and explore the historical scenery for a relaxing and restorative mini-vacation.

Where to stay: This four-person contemporary barn-house is the perfect blend of modern and old-fashioned. It also happens to be situated on 70 acres (28ha) of woodland, with two fresh water ponds and jaw-dropping views of the Green Mountains, leaving you plenty of room to stretch your legs in the most scenic of locations.


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Rural village scene in town of Grafton in Vermont, USA
Rural village of Grafton | © incamerastock / Alamy Stock Photo

Discover Grafton’s scenic beauty and historic buildings for a glimpse into America’s early colonial days. In the 1800s, Grafton was a popular stagecoach stop for those traveling to Albany, New York through the Green Mountains. As a result, the area acquired a market for hospitality, and maintains the Grafton Inn, which dates back to 1801 and remains one of the oldest operating hotels in the United States. Many of the town’s original buildings have been preserved in order to keep its authentic New England atmosphere. Visitors can enjoy snow-covered hills and cross-country skiing, or wander the town’s array of shops and galleries.

Where to stay: This adorable two-person cabin is built with wood from the surrounding forest. Delightfully decorated, it’s small but incredibly cozy. With a hammock and an outdoor fireplace, its secluded location next to a rushing brook makes it the most peaceful of escapes.


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© Jon Arnold Images Ltd / Alamy Stock Photo

A popular tourist destination for New Yorkers, New Englanders and even Europeans in recent years, Manchester is well known for its factory outlets and local businesses. Located in Bennington County, the town is a great base for skiing and hiking in the surrounding Vermont countryside. Manchester village has a vibrant cultural scene with shops, museums, galleries and theatres showing concerts and plays. Visitors can tour old buildings, peruse craft fairs and dine in one of many artisanal restaurants and cafes.

Where to stay: Within walking distance of central Manchester, this classic New England house can house up to six guests in its sophisticated furnishings. With a huge living area, plenty of garden space and even a nursery room, this one is perfect for the traveling family.


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State Street in downtown, Montpelier, Vermont, USA
State Street in downtown Montpelier | © Ian Dagnall / Alamy Stock Photo

Montpelier may be the state capital of Vermont, but as the smallest state capital in the United States, it has all the charm and character of a picturesque town or village. Nevertheless, it boasts a vibrant cultural scene with something for art, music, history and nature lovers alike. Visit the Vermont Historical Society Museum, the TW Wood Art Gallery and the Vermont State House for lessons in local history, or wander Hubbard Park and visit the farmers’ markets for a taste of day-to-day Montpelier life. Home of the New England Culinary Institute, Montpelier is also a great place to eat out, whether in lively restaurants or cute cafes.

Where to stay: This tucked-away studio flat, a 10-minute walk from downtown Montpelier, strikes the perfect balance between peace and convenience. Overlooking a large garden with pear trees, fruit-bearing bushes and beautiful peony flowers, it won’t take long to get home, but once you do you’ll feel a million miles away from civilization.


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© Joanne Pearson / Alamy Stock Photo

Located on the shores of scenic Lake Champlain, Shelburne is a lush and affluent suburb of Burlington, Vermont’s largest city. Shelburne has three main tourist attractions – the Shelburne Museum, Shelburne Farms and the Vermont Teddy Bear Company – in addition to a nature park and a lakeside beach. Roam the 19th-century Shelburne Farms estate, complete with a 110-room summer residence, a five-story barn and a two-acre (0.8ha) courtyard with hayrides. History buffs can learn about Vermont’s heritage at the Shelburne Museum, where American art and an original steamboat are the main draws.

Where to stay: Enjoy stunning views of the lake from every room in this five-person house. Overlooking Shelburne Bay, this modern home sits directly on the shoreline and, in the heat of the summer, provides a couple of kayaks for you to go out and enjoy the water.

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  • Stowe

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    Main Street, Stowe, New England, Vermont, USA
    Main Street, Stowe | © Peter Conner / Alamy Stock Photo

    The lively town of Stowe is an ideal destination throughout the year, but attracts particularly big crowds every winter thanks to the popular Stowe Mountain Resort. In town, visitors can wander arts and crafts fairs, museums and galleries, attend musical and theatrical performances and take part in seasonal activities like outdoor film festivals. Stowe is also world famous for its rolling green hills in summer and the vibrant fall foliage which follows.

    Where to stay: Mountainous views are even better when enjoyed from the comfort of an outdoor hot tub, which is exactly what you get in this private four-person apartment just five minutes’ drive from Stowe. With access to a large backyard and a natural outdoor swimming pool, pick your spot and spend an evening enjoying the amazing scenery.


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    View of Waitsfield Covered Bridge (aka the Eddy Covered Bridge) crossing the Mad River, in Waitsfield, Vermont.
    Waitsfield | © Paul Freeman Photography / Alamy Stock Photo

    Located in the heart of the Mad River Valley in Washington County, Waitsfield is a popular destination for winter sports lovers in search of backcountry skiing in the area around Sugarbush Resort and Mad River Glen. As is common throughout Vermont, the natural beauty surrounding Waitsfield has drawn numerous talented artists over the years, and today Waitsfield is home to a number of galleries and studios that are open for tourists to visit. Those who love the outdoors can visit several farms, roam farmers’ markets and take guided hiking tours in the hills.

    Where to stay: Release your inner child with six other friends at this luxury treehouse found amidst thousands of acres of wilderness. Once you’ve gotten over the excitement of this brilliantly designed home, there’s so much outdoors to enjoy, from campfires and balconies to a whole host of great hiking trails.


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    © Bill Bachmann / Alamy Stock Photo

    The small town of Weston, located in Windsor County, offers visitors an authentic New England country experience. It’s home to several charming B&Bs, inns and lodges – perfect for a cozy romantic weekend or a fun family getaway. Around town, there are shops selling crafts and artisanal goods, art galleries and craft studios – all of which are still family-owned and operated. Weston is the perfect place for a quiet change of scenery in a picturesque town with a charming and well-preserved heritage.

    Where to stay: This four-bed riverside cottage, originally built in 1900, is just a five-minute walk from central Weston and a 15-minute drive to ski territory. The cozy balcony overlooking West River will quickly help you forget just how accessible this classic New England home is.


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    Woodstock, Vermont - September 30th, 2019:  Small shops and restaurants on a cool Fall day in the historic New England town of Woodstock.
    Small shops and restaurants in Woodstock | © Jennifer Lobo / Alamy Stock Photo

    The shire town and capital of Windsor County, Woodstock is one of Vermont’s best assets. The town was settled in the mid-18th century and is considered the “quintessential New England village”; picture a quaint village green, lined by a mix of restored Greek Revival and Georgian-style homes, all within short walking distance of old country farms and parks. In the town center, visitors can sample maple syrups and cheeses at Sugarbush Farm, and explore the Marsh-Billings-Rockefeller National Historical Park. Go in fall to attend the Billings Farm and Museum‘s annual Harvest Weekend, or simply enjoy the picturesque surroundings, beautiful year-round.

    Where to stay: You won’t find a barn-house as impressive as this six-person conversion in the whole of Vermont. With a completely open-plan design, dramatic wooden beams and soul-warming stone fireplace, you’ll never want to leave this warm hug of a home.

    These recommendations were updated on January 5, 2021 to keep your travel plans fresh.