Rutland Vacation Rentals

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About Rutland

Rutland, nicknamed “Rutvegas” for its lit-up downtown strip, is a beautiful country town surrounded by leafy rolling hills in Vermont. With easy access to the Green Mountains, this small New England town attracts visitors lured by its many outdoor options and cultural attractions throughout the seasons, combined with a noticeable lack of crowds. Our cozy vacation rentals let you experience Rutland’s charming colonial atmosphere and fun activities as only a local can!

Where is Rutland, VT?

Rutland sits along the intersections of Highway 4 and Highway 7 in Central Vermont, 65 miles north of the Massachusetts border and 20 miles east of the state of New York. Once a tiny hamlet during the early 1900s, Rutland grew to become the third largest city in Vermont, behind bustling Burlington and South Burlington, despite having a population of only 16,495 residents.

Things to Do in Rutland, VT

Set your sights on boundless recreation in the surrounding Green Mountains when you stay in one of our vacation rentals, with thrilling activities for all ages just outside the town’s central square. Lace up your hiking boots and head over to Pine Hill Park for a day of outdoor exploring 325 acres of nature via trails and mountain bike single-track, with vistas highlighting exceptional fall foliage and even possibilities for snowshoeing during the winter. 

After communing with the great outdoors, tour the Norman Rockwell Museum, which is housed in a classic red barn on the northeast side of town. Here, you can browse original works depicting small-town life by the celebrated painter and one-time Vermont resident. If you’ve brought children along, take them to the Wonderfeet Kids Museum for playing with interactive, educational exhibits like a block puzzle, reading chair, magnetic wall, and clay modeling table.

When hunger strikes, you’ll find plenty of options for fresh fare along West and Wales Streets in downtown. Grab a slice of wood-fired pizza and wash it down with a pint of brewed-on-site beer at the Hop ‘N Moose. Or, you might opt for an authentic Japanese dining experience at the Tokyo House or savor rotisserie bites at Table 24. Of course, you might just want to cook your favorite dishes in the comfort of your own rental kitchen (we won't tell).

Day Trips from Rutland, VT

During winter, strap into your snowboard or skis for some of the region's best slopes at Killington Ski Resort, 17 miles east. Dubbed "The Beast of the East” for its 3,050 feet of vertical drop from a 4,229-foot summit, this resort boasts an annual snowfall of nearly 250 inches over 1,509 acres of terrain with 155 runs, making it a favorite destination among winter sports enthusiasts. But it’s also a respected summertime mecca for mountain biking, hiking, and rock climbing, along with offering family fun at the adventure center, which includes the Beast Mountain Coaster, a four-story ropes course, 600-foot-long zipline, and other amusement park activities.

Vermont is also known for picturesque country backroads, and you’ll find some of the best on an invigorating road trip in virtually any direction you go from your vacation rental. Wind around Highway 100 to explore tiny Pittsfield and its green pasturelands 20 miles northeast, or head 30 miles south to the colonial village of Dorset , where you can pick up some authentic Vermont maple syrup and Cabot Creamery cheese at the H.N. Williams General Store, then catch an off-Broadway play at the Dorset Playhouse.

Wherever your interests lie, rest assured you’ll find what you’re looking for a short jaunt away from any of our vacation homes in Rutland. Book one today for worry-free lodging and front door access to all the best of Central Vermont!