About Chester

Chester Today

The village of Chester is located in southern end of a region known as the “Heart of Vermont.” New York, Boston, and Hartford are all within a comfortable driving distance, yet we are far enough North to get a good snowfall for all wintertime activities.

Life in Chester centers around the Village Green. The Chester House Inn is located on the North side of the Green. Also located on and near the Green are restaurants, a country store, art galleries, clothing shops, gift shops, book stores, a teddy bear shop, a quilt shop, a cafe, a leather shop and the Chester Historical Society.

In the summer and fall, activities on the green include craft fairs, art shows, children playing and bicyclists resting aching muscles after a long bike ride. Of course you can sit in a rocker on our front porch and watch village life pass by on any day. And on Memorial Day and on Alumni Day (in June), you’ll have a front row seat for the parade.

The Chester of Yesterday

Chester_house_drawingIn 1764 the original charter was granted by New Hampshire to the town of Flamstead. The first town meeting was held in 1765 after which a 1766 New York State charter claimed the town, now renamed “Chester.”

One of the first colonial Declarations of Independence was adopted at a Chester town meeting on November 10, 1774 – twenty months before the Continental Congress in Philadelphia. Vermonters fought in the Revolution, insisting on Statehood of their own rather than becoming part of New Hampshire or New York. We remained an independent republic until 1789.

Many stagecoach inns were operated in Chester, with a stage line from Boston to Montreal intersecting here with a line from Hanover to Albany. In 1849, the railroad from Boston to Lake Champlain was completed and Chester became a commercial and shipping hub.

Chester is located at the convergence of three branches of the Williams River and offered fertile soil for farming to the early settlers. Farming, transportation and industry brought prosperity to Chester which helped build the many Colonial and Victorian homes along main street. Early in the 20th century, industry moved East, but Chester nonetheless retains to this day the elegance and charm of a Colonial New England village in the rural countryside.

Client Testimonials

Interested in staying with us? Read some comments our guest's have left for us:

As always, we had a great time!  Thank you for everything.   See you both again soon!

Lynne and Danny O.

Fairfield, Connecticut

Sometimes when my mind is wandering I will find myself back at the inn.  I immediately get a warm and comforting feeling mainly because you both made two complete strangers feel so welcomed by your wonderful hospitality. 

Our best wishes.

Ken and Janis V.

West Haven, Connecticut

On behalf of the Monitoring Team, I would like to thank you for your hospitality this week.  My team was very pleased with your establishment and the reports back to me during the week were glowing.  You were very gracious and flexible.  We will certainly recommend you to our co-workers and friends!

Judy C.

Vermont Department of Education

All your recommendations — from restaurants to ski rental to maple syrup — were so helpful… Finally, we were deeply touched by how welcome you made or 10-year-old son, Evan, feel. You made him feel special, smart and grown-up. This was an unexpected gift you so generously gave us. We wish you nothing but great success and hope to see you back on our next trip north to ski.

Lillie, Mark and Evan O.

Tenefly, New Jersey

Thanks a million for everything, for all that you both did to make our stay in your inn an extra special time.  We appreciate so much the warmth and comfort we experienced.  Your gourmet breakfasts and attention to our needs was so much appreciated. as were your dining recommendations. God’s blessings on you both.  Hope to see you again soon.

Mary & Mario T.

Cortlandt Manor, New York

Thank you very much for making our stay in Chester so special.  We had a wonderful time at the Chester House Inn and we plan on coming back for another visit real soon.

Danielle & Joey

Lindenhurst, New Jersey

The Chester House has been a delightful home during my stay. Especially memorable are your culinary presentations and care shown to every guest.

You have both obviously devoted years on the decor, ambiance and historical presentations. Thank you for your T.L.C.

Pat E.

Concord, CA

As always, we had a great time!  Thank you for everything. See you both again soon!

Lynne and Danny O.

Fairfield, Connecticut

We see that you finally received the much needed snowfall and we hope the skiers are all packing up their cars and heading your way. We wanted to let you know how much we enjoyed our stay in your beautiful, comfy Inn. The room (#7) was perfect for our 3-person family, and the morning breakfast sent us to the slopes every morning smiling, happy and quite full. We looked forward to coming back every night and sitting in front of the fire in the Keeping Room while we got our evening fix of Olympics.

Lillie, Mark, and Evan O.

Tenefly, New Jersey

This is an open recommendation to all first time visitors:

These innkeepers take your visit personally.  They talk with you, not to you and really want to make your stay special.  If our room is indicative of the others, it shouldn’t matter which one you select.  Warm, tastefully adorned and most comfortable.  The gathering room is inviting with a gently stoked, meticulously maintained fire.  Breakfasts are a hand-crafted, culinary delight.  This B&B is a value, period.

Bob and Jeri C.

Marlborough, Connecticut

I want to thank you or a wonderful weekend.  We had a very enjoyable, relaxing time the Chester House.  You made us feel like we never left home. You were fantastic hosts. We were a little sad to leave. Vermont is beautiful and we hope to see it in the winter time.  I will definitely spread the word about the Chester House to everyone I know.  The work and dedication you both put in to making everyone “feel at home” shows.  So we thank you again for a very enjoyable weekend.

Christine & Ralph

Deer Park, New York

Thank you for being a big part in making our first visit to Vermont a memorable and beautiful one for us. Your Bed & Breakfast is so charming and your love for detail is obvious.  We felt very comfortable in Room #1 and I loved hearing about the history of various pieces of furniture throughout the inn. And your delicious breakfasts were a perfect start for a day of exploring.  Thank you! Your warm and welcoming personalities make us want to come back soon.


Anke R.

Hyde Park, New York

Thanks so much for your hospitality this weekend. My Mom and I had a great birthday weekend and enjoyed the cozy room.
We hope to see you again soon!

Libby F. & Ottile

Astoria, New York

Kathy and I just wanted to say thank you for your hospitality.  We loved our stay and had a great time checking out the area.  We even had fun finding the Hamilton Falls.   🙂  We look forward to staying at your B&B next year for our 31st Anniversary and really look forward to dining at Bella Luna again.

Ray & Kathy J.

Watervliet, New York

Just a note to thank you for our wonderful stay at the Chester House.  We all agreed it was one of the highlights of our vacation,  We love Vermont, your Inn, and your comfortable hospitality!

Deb, Freddie, & Chris L.

Ogden, Utah

Just wanted to thank you again for the great stay at the Chester House, loved breakfast… we are now thawing out back
in Maui, if you ever get our way, come stay with us. Aloha!

Janna and Richard H.

Maui, Hawaii