Chester, VT is located in Windsor County, Vermont. Originally named Flamstead in its charter of 1754, the town was later named Chester after the eldest son of King George III, the Earl of Chester.

Chester Depot, just the other side of the old Rutland Railroad tracks from the town, is home to Chester’s "stone village" – a street containing numerous houses made of local granite. The stone village is listed in the National Register of Historic Places and has made the town a popular destination for Vermont tourists.

Driving time to Chester is approximately 3 hours from Boston, 5 hours from New York City, 4 hours from Montreal, 2 hours from Albany, and 2 hours from Bradley International Airport (Hartford).

Like many Vermont towns that were thriving nineteenth century transportation hubs with quarries and manufacturing activity, Chester generated wealth. Today, the remains of that wealth are on display in Chester many antique shops.

Today, the Green Mountain Flyer offers rail excursions between Chester Depot and Bellows Falls, with beautiful views of the Connecticut River and the central Vermont countryside. Tourism is a driver of the local economy, and Chester is home to many bed and breakfast inns.

Chester Village is located in the heart of Vermont, and is within one to two hours driving time of almost all of Vermont’s best golf courses, ski resorts, restaurants, and other attractions.

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Romantic Vermont Inns and B&Bs

Addison Bed and Breakfast	Arlington B&B	Barnard Vermont Hotels	Barre Vermont Lodging	Bed and Breakfast Bennington	Brandon VT Lodging
Hotels Brattleboro VT	Bridport Vermont Hotels	Bristol Vermont Hotels	B&B Burlington VT	Chester Inn Vermont	Colchester Vermont Motels
Derby Vermont Hotels	Dorset VT Hotels	Essex Junction Vermont Hotels	Grafton VT	Jamaica	Jay VT
Jericho	Killington Lodges	Londonderry VT Hotels	Ludlow	Manchester VT Lodging	Manchester Center
Marshfield	Hotels Middlebury VT	Montgomery VT Lodging	Montpelier	Mount Snow	New Haven Vermont
Norwich	Okemo	Peru	Poultney	Putney Vermont Hotels	Quechee VT
Randolph	Rochester	Hotels in Rutland VT	Saint Johnsbury	Salisbury	Saxtons River
Hotels Shelburne VT	South Burlington	Springfield	St. Albans	Lodging Stowe VT	Stratton
Townshend	Vergennes	Waitsfield	Wallingford	Warren	Waterbury
West Dover	Weston	White River Junction	Williston	Wilmington	Inn Woodstock VT