Chester, VT, USA

We found 806 vacation rentals — enter your dates for availability

Chester, VT, USA

Chester vacation rentals

A slice of New England in Chester

With its red-brick buildings and characterful high street, Chester embodies everything that's great about America's New England communities. It's now listed on the National Register of Historic Places, which makes it a great place to discover history, culture, and the Vermont countryside. The atmosphere is unique, so why not stay local with downtown Chester vacation rentals housed in beautifully renovated Victorian buildings? Beyond its downtown charm, Chester serves as the gateway to Okemo Mountain Resort, as well as some of Vermont's most beautiful national forests.

Get the adrenalin pumping on Okemo Mountain

Rising above the nearby village of Ludlow, Okemo Mountain Resort'is a 4-season outdoor playground. In winter, the mountain serves up some of Vermont's best downhill skiing. When the snow melts Okemo's Adventure Zone offers everything from ziplining and rock-climbing to segwaying and mountain biking. If you're serious about your par, Okemo boasts a pair of 18-hole championship golf courses complete with spectacular mountain vistas. Just 45 minutes away, Manchester is a popular day trip. From touring the grand Hildene Estate to visiting the American Museum of Fly Fishing, the town is full of quirks.

Turn back time in Chester's Stone Village

Chester is best known for its Stone Village Historic District, where you can wander along streets lined with greyscale granite homes. Downtown, you'll find the Chester Village Historic District, showcasing a medley of Victorian, Colonial Revival, and Federal style architecture. From 19th-century stone cottages to wood-paneled carriage houses, Chester vacation rentals give you a chance to live and breathe history. Why not continue the theme with a ride on the Green Mountain'Railroad, which steams past rising mountains, sparkling rivers, and historic towns?

Mountains, forests, and Finger Lakes'Fishing

Towering over 3000 feet high, Okemo Mountain dominates the landscape. If you'd rather escape the crowds, you'll find off-the-beaten-track hiking trails in nearby state forests like Okemo and Proctor Piper. Hawks Mountain Wildlife Management Area is another backcountry favorite, with the chance to spot black bears and white-tailed deer. Both the Green Mountain'National Forest (GMNF) and the'Finger Lakes'National Forest (FLNF) offer some of the state's best fishing, though you'll need to pick up a license before you cast a line.