Welcome to the Chesterhouse Inn!

Experience Vermont in comfort and class at the historic Chester House: an elegant, warm and friendly Colonial American Bed and Breakfast on the Village Green in the classic and quaint town of Chester VT, conveniently located just 44 miles from Vermont’s southern border via I-91.

We offer you the ambiance of yesteryear combined with 21st century conveniences and luxuries such as in-room TVs, WiFi Internet wireless access, Jacuzzi and whirlpool tubs, fireplaces, air conditioning, etc. Our large, beautiful, clean and comfortable suites and rooms are tastefully decorated with authentic antiques and heirlooms, and each has its own private bath.

With its elegant but relaxed atmosphere, the Chester House is an ideal hub for your Vermont vacation, your romantic getaway, your adventure — however long or short it may be.

If you want to treat yourself right, then reserve a room for yourself at the Chester House, where you will be hosted by friendly innkeepers who will “treat you like family” without suffocating you. And our rates are quite reasonable and affordable.

Our hallmark is as a romantic getaway: we can host your engagement or anniversary trip to Vermont, your honeymoon, your small Vermont wedding, or a special birthday. We can also host your business trip or an event with a group of up to 16 persons.

There’s a lot to do here in our “neck of the woods” in any season: Winter, Spring, Summer or Fall: antiquing, biking, boating, fishing, golfing, hiking, horseback riding, leaf peeping, motorcycling, cross-country skiing, down-hill skiing and snowboarding (we have some great Winter ski packages, partnering with Okemo Mountain), snowmobiling, snowshoeing, outlet shopping, visiting wineries, breweries, country stores, covered bridges, art galleries, museums, and crafters’ studios. Check our Things To Do Page in the menu on the left for details.

So look around our website and see how wonderful a stay at the Chester House can be. Look at our Suites/Rooms Page and check each suite/room’s amenities. Pick the one that suits you best, where you can relax and get away from your normal routine for a while. After checking our Availability Page, please give us a call to make your reservation.

We’re here to help you have a wonderful time in Vermont. That’s what, for years, our guests have said we’ve been doing.

We hope to hear from you!

Jan and Bob,

Client Testimonials

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

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

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

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

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

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

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

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

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

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

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

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

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

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