Places to stay in Chester, Vermont

Chester is a town in Windsor County, Vermont. The town was originally chartered by New Hampshire Governor Benning Wentworth as Flamstead in 1754. The terms of the charter were not met and the town was re-chartered as New Flamstead in 1761. In 1766 a third and final charter was granted and the town became Chester, named after George Augustus Frederick, the Earl of Chester and the eldest son of King George III. Local dining options include Vermont Cannoli, The Free Range, Country Girl Diner, and The Phoenix Cafe.

If you are travelling in the area, Chester is located close to First Baptist Church, Duttonville Gulf, Glebe Mountain, Coffeen Cemetery and Vermont Academy.

The center of Chester ( which is at is longitude -72°35'40.416 and latitude 43°15'46.44 ) is located 6 miles away from Grafton, 7 miles away from Springfield, 9 miles away from Cavendish and 9 miles away from Perkinsville.

Available Chester lodging

We currently have 16 accommodations in and around Chester.

Chester Hotels, Motels, Resorts, B&Bs and Extended Stay

Bed & Breakfasts

Inn Victoria

Conveniently located on The Green in picturesque Chester Vermont near Okemo Mountain. Built in 1851, this elegant Victorian B&B provides the perfect location for couples to enjoy an intimate, relaxing getaway.

321 Main Street

Chester, Vermont

Hotels

Stone Hearth Inn

Slow down and enjoy Vermont’s four-season environment and relish its everyday gifts. We invite you to join us for a genuine experience that embraces both relaxation and adventure. Our friendly atmosphere and Vermont’s natural beauty create a memorable experience for all who stay with us..

698 Route 11 West

Chester, Vermont

Bed & Breakfasts

Chester House Inn

Historic, romantic, cozy B&B in Chester VT for getaway, golf, skiing vacation, lodging, accommodations, accomodation. We offer you the ambiance of yesteryear combined with 21st century conveniences and luxuries such as in-room TVs, WiFi Internet .....

266 Main Street

Chester, Vermont

Bed & Breakfasts

Henry Farm Inn

Nestled between a sloping meadow and sparkling river, with fifty-six acres of forested foothills and a spring-fed swimming pond, the Henry Farm Inn is a haven of tranquility in a natural setting.

2206 Green Mountain Turnpike

Chester, Vermont

Bed & Breakfasts

Rose Arbour Bed & Breakfast

You'll find Rose Arbour just off the green in Chester, VT in a classic 1890 New England Victorian house.We have taken pains to furnish and decorate the rooms such that they ease you into a slower pace whether through a relaxing evening in Rose .....

55 School Street

Chester, Vermont

Bed & Breakfasts

The Fullerton Inn

This Southern Vermont Inn combines elegance and luxury with the comforts of home. When you stay with us, you will get the best of both words: the feeling of being treated like honored guests in our home, with all of the privacy and luxury that a vacation calls for.

40 The Common

Chester, Vermont

Bed & Breakfasts

Old Town Farm Inn

Escape! To the outskirts of Chester, Vermont. To Vermont's Okemo Valley. We're only a few hours from the eastern seaboard, yet a world apart from big city living. The Old Town Farm is a classic 1861 Vermont B & B right in the heart of the Okemo Valley region.

665 VT Route 10

Chester, Vermont

Bed & Breakfasts

Stone Cottage Collectables Bed And Breakfast

Enjoy a nostalgic trip back in time at Stone Cottage Collectables Bed & Breakfast. Our 1840 stone house is located in Chester's "Stone Village" Historic District, a grouping of eight private homes, Stone Church and Stone Schoolhouse, all built between 1834 and 1845.

196 North Street, Route 103

Chester, Vermont

Motels

Motel In The Meadow

★★★★★★★★★★

20 minutes from Okemo base lodge, 25 minutes from Bromley Mountain, 10 minutes from Magic Mountain, 10 minutes from Tater Hill Country Club. Accommodations including kitchenettes and family rooms, cable TV, AC, snowmobile trail access, cross-country skiing and snowshoeing.

"I have stayed at Motel in the Meadow several times and it is a very nice place to stay. The owner,Pat Budnick is the friendliest person and offers a free Continental Breakfast. The rooms are ..... "

936 Route 11W

Chester, Vermont

Bed & Breakfasts

Hugging Bear Inn And Shoppe

Stay in one of 5 guest rooms blending 19th century charm and modern touches each with a private bath. Rooms accommodate couples singles families and children.

244 Main Street

Chester, Vermont

Bed & Breakfasts

Popple Fields Bed And Breakfast

1300 Popple Dungeon Road

Chester, Vermont

Hotels

The Inn At Cranberry Farms

The Inn is situated on 60 acres of rolling meadows and forested farmland that includes a serene pond, spectacular views of the Green Mountains and it is just a short walk from the Inn to the Williams River. Whether you are on a romantic getaway, .....

61 Williams River Road

Chester, Vermont

Quail Hollow Inn

Bed & Breakfast

The Quail Hollow Inn in the lovely town of Chester, Vermont is a four-season bed & breakfast in one of the most scenic parts of Vermont. No matter what time of year you come to visit, there is always something to do. In the fall, Southern Vermont is famous for the best color in the Green Mountains.

225 Pleasant Street

Chester, Vermont