Ever since the legendary Bing Crosby enjoyed a “White Christmas” in Vermont, the area has been the go-to place for magical Christmas getaways. With 20 alpine ski resorts offering thousands of acres of scenic mountain terrain, criss-crossed by hiking trails and skiing slopes, Vermont is a great escape for city-dwellers from Boston, which is located 200 miles to the south, as well as New Yorkers, which takes a 340-mile journey of around six hours. Book a stay at a Vermont vacation rental for the Christmas season, and you’re almost certain to get snow. No matter the weather, you can look forward to festive experiences in the pretty towns around Vermont. Here are the seven best Christmas getaways in this New England state.
1. Woodstock
Woodstock has been attracting visitors from Boston and New York since the 1890s. Arrive at your vacation rental in time to enjoy the annual Woodstock Wassail Weekend — the most elaborate winter celebration in the whole of Vermont. Visitors receive a warm welcome and are invited to join in community events, concerts, indoor performances, outdoor spectacles, and feasts. Public buildings and museums are decorated in magnificent style. On Saturday, a parade of horses and wagons with costumed riders circles the village green, where Father Christmas oversees the lighting of the yule log and memory tree while the carolers sing. Spend time wandering the streets, visiting some of the elegant private homes that are open for tours. Above the town, the Rotary Club’s Christmas Star shines down from Mount Tom with its beautifully groomed ski trails.
Find vacation rentals near Woodstock
2. Grafton
Stay in a vacation rental in Grafton, and feel like you’re entering the scene of a pretty Christmas card. Grafton’s collection of traditional New England clapboard and brick houses dates back to the early 1800s and looks even more charming when decked with snow. In preparation for Christmas, the local community put up at least 250 colorful wreaths and around 3,000 yards of roping. In addition to the traditional outdoor pursuits of cross-country skiing on the carefully groomed 30-kilometer trails at Grafton Ponds, plus tubing and ice skating, visitors are warmly invited to visit the Grafton Village Cheese factory — proud producer of Vermont’s prize-winning cheddars. Here you can see how the milk from the Jersey cows is transformed into blocks of cheese, and sample the goods.
Find vacation rentals near Grafton
Find the perfect Vermont vacation rental on Tripping.com. Tripping.com is the world's #1 vacation rental search engine with over 10 million properties!
3. Chester
Residents of Chester describe their little town Chester as “the Vermont you’ve been hoping to find.” As it is located at a crossroads, visitors to Chester have a choice of four different ski areas to head out to each day. Visit in early December to enjoy carol singers gathered on Chester’s green to sing songs around the lighted Christmas tree before joining everyone at the Fullerton Inn for steaming cups of cocoa. In addition to winter sports, this charming village is home to Bonnie’s Bundle Dolls, where owner Bonnie invites visitors into her home to inspect her collection of one-of-a-kind cloth dolls. Artist galleries include Tsuga Studios, which is normally open by appointment only. On one weekend in December, glassmaker Nicholas Kekic hosts an open house and holiday sale. Look for handblown glass Christmas ornaments and richly colored bowls and pitchers.
Find vacation rentals near Chester
4. Burlington
Burlington, Vermont’s largest city, is a lively community based on the shores of Lake Champlain. Take a vacation rental here, and you have access to a thriving arts scene, museums, galleries, and festivals. The festive season kicks off in style with the Church Street Santa Parade and Lighting Ceremony in late November. The entire street and market place, along with the 50-foot holiday tree, is lit up with thousands of colored LCD lights. The magic continues in December when the Green Mountain Railroad runs special events from Burlington Station, such as the Jingle Bell Express with goodies and singing, and the Polar Express where kids enjoy an enchanting performance, a train ride, hot chocolate, cookies, and a bell from Santa.
Find vacation rentals near Burlington
5. Middlebury
The pretty little town of Middlebury hosts a whole month of festive fun in December. Hunt through local stores, and enjoy an old-fashioned visit with Santa, craft sessions, singing, and dancing. There is also an annual gingerbread house contest and exhibition. For winter sports, the Middlebury College Snow Bowl offers family-friendly experiences, and the Rikert Nordic Center has an impressive snowmaking system to ensure maximum snow coverage.
Find vacation rentals near Middlebury
6. Manchester
Manchester celebrates the spirit of the season with its Merriment Festival. The fun begins with the tree-lighting ceremony on the green in November and continues with events such as the lighted tractor parade, when tractors old and new travel through the town lit up like Christmas trees. Little ones love the chance to ride on the Elf Express. This hour-long trip aboard the vintage Green Mountain Flyer includes singing and dancing elves, hot chocolate and cookies, and a visit from Mr. and Mrs. Claus.
Find vacation rentals near Manchester
7. Stowe
This lively town is a fabulous destination year-round and is especially popular in winter thanks to its proximity to Mount Mansfield, the highest point in Vermont. In addition to cross-country skiing and snowshoeing along the local trails, and ice skating at the Stowe Arena, enjoy sleigh and carriage rides, Stowe at night lantern tours, Ben & Jerry’s ice cream tours, and children’s toy and painting activities. Wander around the boutiques, art and craft galleries, and the glass blowing studio to pick up gifts.
Find vacation rentals near Stowe
Ready to go? Check out these amazing Vermont vacation rentals on Tripping.com.