Winter!

The Chester House in Winter
The Chester House in Winter

CHESTER, VT — Winter brings tremendous smiles to lovers of winter sports and outdoor activities in Vermont!

Many Chester House guests have found a romantic sleigh ride a nice addition to their winter visit to Vermont.

The Chester House is ready with its Stay and Ski / Board packages, with substantial discounts both on the room and on the Okemo lift tickets. Even most “peak weekends” and Presidents Week, Chester House guests will save on their snow getaways.

We also have a package for Cross-Country Skiing and Snowshoeing at Grafton Ponds!

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Client Testimonials

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

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

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

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

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

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

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

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

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

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

Lynne and Danny O.

Fairfield, Connecticut

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

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

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

Lynne and Danny O.

Fairfield, Connecticut

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

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

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