About the Inn

The East side of the historic Chester House on Main St., Chester, VT .
The East side of the historic Chester House on Main St., Chester, VT .

Located on the Village Green in Chester VT, the Chester House, is one of the most beautiful and historic structures in the town. Built in 1780 and charmingly maintained through the centuries, the Inn and its guest suites and rooms are furnished and decorated throughout with family heirlooms and collected antiques that reflect the genteel lifestyle of colonial America.

Just 38 miles north of Vermont’s southern border with Massachusetts, the Chester House is centrally and conveniently located for year-round indoor and outdoor adventures. And being right on the quaint Village Green puts us across the street from fine restaurants and interesting shops.

The central part of the Inn was built in 1780 and exudes the charm of colonial America, with wide plank pine floors, a beautiful staircase and wooden shutters. The building is part of Vermont’s earliest history and is listed on the National Register of Historic Places.

The Inn has seven beautifully-appointed guest rooms; four of these are suites. Click here to view our guest rooms page for room pictures, rates and descriptions.

The Chester House Entrance Hall with its Colonial American charm.
The Chester House Entrance Hall with its Colonial American charm.

Each of the seven guest rooms has its own private bath, a phone (with free calling to anywhere in the USA, Canada, Puerto Rico, US Virgin Islands, Guam, and Saipan), voice-mail, air conditioning in the warmer months, and both free wireless (WiFi) and dial-up Internet connectivity. Five of the rooms have gas fireplaces which operate in the cooler months. Several have luxurious canopy beds and a comfortable sitting area. One rooms has a whirlpool, one a Jacuzzi, and another a two-person steam shower.

At the center of the Chester House is the Keeping Room with it’s original 1780 wood-burning grand fireplace. Guests enjoy the Keeping Room for reading, TV, board games or just sitting in front of the roaring fire (in winter).

Adjoining the Keeping Room is the Dining Room with its majestic copper, brass and wood ceiling. Here we serve a full gourmet breakfast daily between 8:00 AM and 9:00 AM. Click here for a hint of what’s in store for you at breakfast. No one heads out hungry for his/her day’s planned recreational activities!

The Chester House is a friendly place and many guests enjoy the ambiance of meeting travelers from other states and other countries. But for some, breakfast is a personal time and they prefer to begin a new day quietly and at their own pace.

In the warmer weather, the open-air deck is a place where guests can enjoy a relaxing time reading, sharing a quiet conversation, or just watching the chipmunks play.

Inn guests playing “catch” in the driveway adjacent to the deck.

Our front porch is another favorite spot for guests to sit and chat, read, or just “watch the world go by.”

Evenings in the summer can be cool so be sure to bring a light sweater or jacket when you come to the Inn in summer.

The Chester House is a smoke-free building. Guests who smoke may do so on the front porch or on the deck.

In 1988 the Inn was equipped with new electrical, heating, plumbing, and smoke and fire detection systems which help ensure our guests comfort and safety.

A paved private off-street parking area for guests is adjacent to the building on the East side. Behind the Inn is an old red barn that reminds us of the bygone era when horses, not cars, were the main method of transportation.

We hope you are able to come to Chester and spend some relaxing time at the Inn. You’ll find that visiting here is, in some ways, like taking a step back in time.


Client Testimonials

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

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

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

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

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

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

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

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

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

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

Lynne and Danny O.

Fairfield, Connecticut

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

Lynne and Danny O.

Fairfield, Connecticut

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

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

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

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