Chester House Inn

Address: 266 Main St, Chester, Vermont, 05143-9768, United States | B&B
Searching for availability...
*Prices above are provided by partners for one room, double occupancy and do not include all taxes and fees. Please see our partners for full details.

How has this b&b rated in the past?

  What's this?
Discover trends in hotel experiences based on real traveler reviews and ratings. Mouse over circles to see what some travelers had to say.


This B&B, located on 266 Main St, Chester, is near Green Mountain Flyer, Eureka Schoolhouse and Baltimore Covered Bridge, and Martins's Maple Farm.
Map this b&b



        Historical Traveler Reviews Chester House Inn

        Chester at its Best


        You will love the Chester, Vt area. I can't think of a better place to enjoy it from than the Chester House Inn. Bill and Paul, the innkeepers will make you feel at home at this quaint Vermont B & B. My wife an I have been visiting the chester area for sometime now and love the hospitality at this inn. Since Bill and Paul took over the inn about 2 and half years ago they have continued and improved on what was and is a wonderful place to enjoy your Vermont stay.

        Like a home away from home!


        My husband and I stumbled across an on-line listing for the Chester House Inn several years ago when we were searching for a getaway to a VT B&B. After comparing the Chester House Inn's amenities, location and charm to those of several other inns in the area, we booked ourselves in for three nights. We so thoroughly enjoyed ourselves on our first visit that we have returned for a winter escape every year since!

        We have stayed in three of the inn's seven rooms, and have found each to be comfortably appointed. Some of our rooms have had gas fireplaces, others have had jacuzzi tubs, and still others have had sitting areas in addition to the sleeping area. Thoughtful touches such as extra pillows & blankets, bottled water, a variety of current magazines, and a binder filled with information about attractions in the Chester area abound.

        The inn's common area is cozy and complete with a fireplace, shelves full of books, racks of brochures about area attractions, an assortment of games, and a TV. We have meet some wonderful new friends while lounging in front of the fire after long days of skiing. The innkeepers, Bill and Paul, have often joined in our conversations and have delighted us with their stories, their knowledge of the inn's history, and their suggestions for just the right place to shop for antiques, get a yummy treat to indulge my sweet tooth, or get a late lunch on the day of our arrival to the inn.

        Breakfast is such a treat at the Chester House Inn! We always wake up with anticipation of the culinary delights sure to await our arrival in the newly renovated diningroom. We have been treated to omelettes, blueberry pancakes, stuffed french toast, yogurt parfaits, maple baked pears, and chocolate chip muffins--yum! Coffee, tea and orange juice are offered in abundance as well. We have also taken advantage of the opportunity to purchase soda, beer and wine from the innkeepers in the late afternoon and early can't beat the convenience or the extremely affordable prices!

        The Chester House Inn has become a home away from home for us. We look forward to our visit each winter, knowing we'll be treated like family.

        We love it!!


        The Chester House Inn is one of our favorite places to escape for a long weekend or several days of rest and relaxation. It is exacatly what you picture when you dream up a Vermont country Inn.

        The location is excellent and the small town feel is unique to this tiny village. The rooms are beautifully decorated with early American collectibles. The warm hosts, Bill and Paul, will indulge you in the fascinating history of not only the house itself but the colorful history of many of it's antiques. It becomes obvious that they adore this home and pour themselves into opening it up for others to enjoy.

        If you love breakfast, be prepared to eat! The food is made lovingly from scratch and you can count on going off your diet!

        There is much to see and do and the hosts are always willing to assist with finding new adventures or arranging a romantic dinnner.

        Bill and Paul really make you feel as if you are staying with family which makes all the difference in the world!

        We love the Chester House Inn and would absolutely recommend a visit!!

        Tim and Joanne

        Stay Away!!!


        There were many approaches in crafting a review of Chester House Inn. I could have chosen to focus on the dreadful mattresses that seemed to be purchased for their sadistic qualities. Or, the breakfast that a not so finicky cat would find repulsive, or the ranting of one of the innkeepers of his disgust with corporate America and how much he has suffered at the hands of his former supervision. Of course, I could have also made water damaged ceilings and foul smelling rooms the highlight of this review. But I'm not. This review will focus on the behaviour that only an unhinged loon could bestow upon their guests. And what, you may ask, drove me to reach out to you, the B&B and Inn patron - a fire log.

        Sitting on the couch at approximately 9:30 PM, after a full day of skiing, we were enjoying the company of another couple who joined us for the New Year's getaway to Vermont. We didn't mind the otherwise frigid temperatures kept at the Inn as we had a nice roaring fire to warm us. But as with fires of the past, this orange and red beast too soon turned in to a fraction of its former self and we once again felt the cold reminder of winter. What's that you say? You see where this is going. Well, move that coffee table out of the way because your jaw will appreciate a softer landing.

        That's right, I requested, politely, additional fire wood. The response - "Sorry, firewood is expensive and we have an exact allocation for the season". In response, I offered to pay for the additional firewood; after all a couple of bucks should never stand in between someone's comfort and enjoyment. Besides, at this point it was freezing. "Sorry", says the innkeeper, "I'm not going outside to retrieve more firewood". Of course, being the brave soul that I am, I was willing to brave the cold and provide for my wife and friends. Once again, "sorry, we can't allow you to go behind the barn". At this point, I decided to try to appeal to his common sense, noting that it was getting very cold. In response, I got "what, you're trying to make me feel bad?". Suddenly, the innkeepers life partner walks in dragging bags of garbage behind him. "Paul" the innkeeper exclaims to his life partner, "these guys want more firewood". "WHAT!!?" exclaims Paul, "the common area is now closed. You only paid for your rooms now go to your rooms or get out", signalling to his life partner to refund our money, because he "couldn't bare to look at our damn faces anymore" at the same time exclaiming "I'm not cooking breakfast for anyone tomorrow, kitchen is closed" (by the way - breakfast is part of the deal). He then catapulted across the room and tore out the TV electrical cord from the receptacle, knocking over a floor lamp and telling us to "choke on it". Whatever that "it" is, one can only imagine.

        As I'm sure you have already concluded, this is not a story about lumber or the current high cost of heating a house in Vermont, but rather deep rooted issues stemming from the outcome of one's personal choices and ensuing self resentment.

        Needless to say, our New Year's weekend was completely ruined, having to bear with the confrontation and the possibility of additional attacks, both personal, or, I'm afraid to say, physical. If you are in search for serenity and are eager to explore what Vermont has to offer, try to avoid the Chester House Inn. As a frequent visitor to this part of the world, I assure you that this is not the experience you are searching for.

        Delightful Inn in Chester, VT!


        What a terrific experience my wife and I had last month when we went skiing in Vermont. We wanted a challenging mountain within driving distance, so we took a weekend ski trip to Okemo and were delighted at the great Ski and Stay deal the Chester House had to offer. We couldn't believe it! We saved quite a bundle on our lift tickets and the lodging. Our trip was surely worth twice what it cost us.

        The Inn is a gorgeous place to stay, right in the heart of the village of Chester, only 12 miles from Okemo. Our room was soooooo beautiful and comfortable, and the steam shower after skiing all day was such a relaxing pleasure!

        The breakfasts we had there were out of this world, and the proprietors are probably the nicest innkeepers we've ever met (and we've been staying at B&B's for years). We felt very much at home.

        The Chester House is a great place to stay, and we're planning to take a summer trip there in July.

        Love and Charm make this Vermont Inn Special


        We found the Chester House Inn to be warm and welcoming from the moment we made the reservation. Bill, one of the owners, gave us perfect directions by e-mail. When we arrived (just 4-1/2 hours out of NYC) Paul, the other owner, welcomed us with a bright smile and warm handshake, and showed us to our lovely room. Each room has its own bathroom, and are especially well appointed. Speak about what each room offers when you make your reservation. There are about 10 rooms.

        The house has a fantastic history, and the owners are very diligently delving into old records to discover what they can.

        Breakfast in the common room on the first floor is country fresh! We stayed 3 nights and each day we were indulged by a fresh new plate of a something Bill or Paul had prepared that morning... warm muffins, tasty baked pears, delicious french toast (perhaps best I've ever had!).

        The common room has a TV for those who want to catch a special show in the evening with a glass of wine or beer, which the Inn is licensed to serve, and Paul will happily start up a fire in anticipation of your company.

        When you finally lay down from your day, you'll have a wonderful rest as the beds are easily as comfortable as any I've been in.

        Lastly, whether you are up for a ski weekend at Okemo in Ludlow (just a short drive from Chester), or Statton, or viewing the fall foliage, or perhaps antiquing, or finally up for hiking, the town of Chester is a wonderful home base. It's quaint and friendly simple street gives you the feeling you've arrived in early 1900s America. Let's hope it doesn't change!



        Charming, Cozy, Endearing, a really wonderful stay!


        I want to thank Paul and Bill for making our stay at the Chester House Inn such a lovely experience. The Inn is simply beautiful, with a country flair and a great history. All rooms are very clean and each room has it's own theme.

        We stayed in room #7 and could not have been happier. We also took advantage of their 'Ski and Stay' package which was such a great deal; for 3 nights bed and breakfast including ski pass for Okemo mountain, which is just a short drive. The breakfasts were very tasty and beautifully presented.

        Bill and Paul put their heart and soul into everything they do and the Chester House Inn is just a part of it, you will not be disappointed! They are sincere and make you feel like you're visiting old friends or family. I believe the german word for it is GemŘetlich.


        Niamh & Friend

        Great Hosts,wonderful time,good breakfasts


        My husband and I went to the Chester House Inn to celebrate our anniversary and Bill and Paul did so much more to make it a memorable time.The food was so good ,I asked for the recipes. Good Luck with the inn,we'll be back

        The most relaxing B&B we've ever stayed in!


        We just had the most wonderful time in Vermont, staying at the classy yet relaxing Chester House Inn in Chester. From the moment we walked in the front door we felt so comfortable and welcome, as if we were members of a new and wonderful family. We felt very, very special.

        The innkeepers are the most charming and hospitable hosts! They did all those little things that make their B&B outstandingly delightful, from their great conversations with us to their expert advice on local sightseeing and restaurants. Their love of the innkeeping business shows.

        The inn is impeccably clean and most relaxing. We felt like we were back in the 1780s with the beautiful furnishings and antiques there. Our room was absolutely gorgeous and so comfortable. The view of the Village Green from the front porch was so relaxing, as we rocked in the chairs and absorbed the peacefulness of the quaint New England town.

        And the breakfasts! Oh, my! They were just superb. Each one was a special treat!

        Every part of our stay was better than we had ever dreamed it could, truly a relaxing and pampered stay. We most highly recommend the Chester House Inn to anyone who is looking for the perfect getaway. Bravo!

        Lovely B&B


        Spent one night in Room 5 in August. Huge, beautifully furnished room. Very friendly inn-keepers and lovely town. Wonderful breakfast. Highly recommended.

        TripAdvisor Reviews Chester House Inn

        4.50 of 5 stars Outstanding

        Travel Blogs from Chester

        To Maggie and Brian's cottage.

        A travel blog entry by vbbennie on Oct 10, 2015

        7 photos

        ... leaking roof?), their bathers hang from a rafter in the middle of the room, the toilet door doesn't close and many other quirky things. I can imagine them really relaxing after a hectic uni semester. Both are Professors at McGill, Maggie's office is directly above Brian's. His speciality is Canadian Poetry. Our Sat Nav is having some pronunciation issues. Had to turn onto Vt Route 15E (Vermont Route ...

        North to Vermont.

        A travel blog entry by vbbennie on Oct 09, 2015

        12 photos

        ... road. The road followed along the Connecticut River (seen from our hotel). Passed through yet another Springfield - think almost every state has one. It has been hard to find accommodation for this weekend as it Columbus Day Holliday for the Americans and Canadian Thanksgiving. It seems everyone wants to holiday in Vermont for the next three days. We did find somewhere, in Killington, a ...

        Pillsbury State Park, Washington City, NH

        A travel blog entry by gsnakehill on Sep 28, 2015

        43 photos

        ... of camping. Funny! The site was private so no one but the Moose would see you. We decided to move because we were really alone out there and there is ************e camping this time of year during the midweek. Campground closes in two weeks. We moved to site 6 on May Pond which was closer to the main road right on the water with beautiful views but not near a pit toilet or water to drink. The only reason I am explaining these ...


        A travel blog entry by mustseemore on Sep 27, 2015

        1 comment, 23 photos

        ... a separate classroom building where lessons occur and every item of kit known to man may be tried. We have both learnt so much and even got to try our new skills on the legendary Battenkill River

        Her view of events:

        Our trip "Upstate" was a long one - another 6 hours driving on fast highways. We had intended to walk over the Hudson River on the famous Boardwalk (more like a massive iron ...


        A travel blog entry by mhfamily on Aug 01, 2015

        4 photos

        ... s Farm Oregon Caves Oregon Wildlife Safari Northern California - Pacific Ocean! Glass Beach, Fort Bragg Jelly Belly Factory, California San Francisco, California Death Valley, California Las Vegas, Nevada! Hoover Dam Grand Canyon, Arizona Painted Desert, Arizona Arches National Park, Utah Grand Junction Playground, Colorado Rocky Mountains, Colorado Shaw and Kit's! Boulder, Colorado ...