Chesterfield Inn

Had the pleasure of staying over the weekend. The place is charming very large room with «not romantic» inconveniently high off the floor King size bed nice balcony. The staff made us feel welcomed and are very friendly. The dinner options are very limited 3 appetizer 7 entrees choices desert and breakfast was excellent. 10 minuets away the town of Brattleboro on the river is a MUST visit several art galleries, cafes and one of a kind shops makes this town really standout

I visited the Chesterfield Inn this past weekend to celebrate my one year anniversary with my boyfriend. From the moment we arrived to the moment we left, the innkeepers and staff made us feel so welcome. The inn itself is beautiful and so comfortable, and the food (we had dinner at the restaurant, and then breakfast the next morning) was incredible. It’s perfectly situated about 10 minutes from Brattleboro, which was a cute town to wander through and explore. I highly recommend this inn for a weekend getaway!

Large room with King bed, our room had a balcony with table and chairs, bathroom spacious. Dining room for dinner was excellent, the duck and steak were on point and desert was terrific: apple cobbler. Only a short drive to Brattleboro.

Being from Hawaii, I am not exactly a frequenter of B&Bs but this place exceeded my expectations. First of all, this is a very large inn reminiscent of a mansion from colonial times and each room is different from the next. Overall, the place is charming, inviting, and run very professionally yet courteously.
Chesterfield Inn even has a fairly extensive menu that extends beyond breakfast which include several gourmet dishes which we had for dinner. The food isn’t going to be the greatest you’ve ever had, but it is of restaurant quality while satisfying your craving for a home cooked meal.
The rooms themselves, as I mentioned, are all unique with a colonial charm, but they did not overlook modern amenities here. There is Wi-​Fi available as well as satellite TV in the rooms and all the linens/​toiletries you’d expect at any hotel. All this, coupled with the inn’s wonderful staff, really makes the experience very easy to recommend.

My wife and I had the pleasure of having our wedding at the Chesterfield Inn, and it was made perfect by Judy and the excellent staff. She accommodated so many last minute requests, including finding a local babysitter for the evening for my two nephews. Judy made it so easy for us to enjoy ourselves and our evening. The food was EXCELLENT, and the complimentary breakfast was special every morning.
We stayed in rooms 19 for two nights and 20 the last night (another last minute decision) and had family in the main inn and in two of the rooms in the Johanna Wetherby Building. Our beds were among the most comfortable I’ve ever slept and almost didn’t make it up in time for breakfast the next day. The fireplaces are easy to use (on a timer) and add a cozy atmosphere to the room.
We debated bringing our dog as we were staying on a pet friendly room, but decided against it. You would never know that pets were in these rooms however because it is so clean. Even my wife, who is allergic to everything had no reaction whatsoever.
Brattleboro is a nearby town that is nice to visit, there is a hiking trail nearby and a Vermont Country Store about 15 miles north. We had a wonderful time at the Chesterfield Inn and started planning our next trip there even before we left!
TIP: bring cash! breakfast is served and although included with your stay, the staff definitely deserve tip for the excellent service.

A wonderful hotel with accommodating staff. Great food with great service too! We stayed the night of our wedding and it was a memory we will cherish.

We had a wonderful time here! It was the 2 of us and our Boxer pup. We stayed in one of their pet friendly rooms. They had plenty of room for us to walk around with our pup on the grounds. We had direct access outside thanks to their annex building that we were in. Right outside our room was a private patio. We were also able to get breakfast delivered to our room so that we would be able to stay with our pooch in the room. Exceptional service, we will definitely visit again.

Rustic, quaint charmin. Nice over night stay. Much better than most hotels/​motels.
Staff was great, friendly and very accommodating.
Rooms were stocked with cds, magazines and books. Nice if you had a long stay.
Dining room was spacious. Fabulous service. Small diner menu. Beef tenderloin with mushroom glaze… amazing! The carrots and green beans that came with it… terrible! No seasoning, nearly cooked. Coffee was my beverage of choice and I was pleased with that.
Overall I would come back.

I did not stay at the Inn, but I wanted to write about the restaurant. The Chesterfield is definitely old school, and they do it very well. You won’t find fussy food or creative dishes, but you will find delicious food prepared with quality ingredients and cooked to perfection. The dining room is spacious and the tables far enough apart that you can enjoy private conversation. The building is an historic farmhouse, so there is a nice sense of tradition and history. The ambiance is lovely with white tablecloths and napkins, but the guests are dressed somewhat informally or «county casual.» The pace of the restaurant is rather laid back, they are offering a relaxed find dining experience, so definitely leave some time to enjoy. I liked the list of appetizers, but honestly, the portions are so generous, I’m not sure how you would eat it all!
Also, as a tip, there is a nice incentive for Unilocal users, a free glass of wine with your entrée when you check in.

Spent a awesome getaway this July 4^th weekend in this lovely inn. Great staffs, great atmosphere, and foods. The dinning menu is so good and the waiter had provided super services. The room is so cute and comfortable. Definitely come again.

My husband and two friends ate dinner last night at the Chesterfield Inn. First, the ambiance was lovely. We sat on the porch. Our server Lisa was terrific, always available to fill glasses and get us whatever was needed. Two of us had wild boar and pheasant sausages as an appetizer. It was divine, and very generous. We passed forkfuls for tasting. The filet mignon was perfect served with delicious peapods and carrots. The pheasant was very good as were the scallops. The desserts were fabulous! Cheesecake, chocolate flourless cake and crème brulee… what could not be good. We’ll be back and will recommend the Chesterfield Inn to our friends without hesitation.

Best Bed and Breakfast in the area! I stayed here for my anniversary at the beginning of November and the service was excellent. The owner has a cat that walks around the inn and is very friendly. The room that we stayed in was very clean and had a deck. When we got there it felt like 60 degrees so we sat out on the deck for a bit. so peaceful! Breakfast was good, they serve homemade muffins each morning and at dinner service as well. The red pepper cornbread muffins were delicious! The Inn is 15 – 20 minutes from Keene NH and other area attractions. I would definitely recommend this place to others!

LOVED this inn!!! My boyfriend and I stayed here for an innkeepers conference for a weekend in March 2013. We were able to take the dog, which was a big plus! The room was spacious, clean and comfy with a fire place and CD player. The staff were all kind and helpful. All our meals were delicious. If it had been better weather we would have loved to wander and explore the property. This was a lovely place and my idea of a quintessential New England Bed & Breakfast!

I went there with my wife and 3 year old boy and I will tell you the owner and her staff are super nice and friendly !!! I would go back there in a heart beat !!! My little boy loved the kitty cat and the owner and the staff let my boy feed him a treat !!! he was super happy about that !!! The rooms are clean and the breakfast was awesome !!! If your a hungry man like me, make sure you order 2 omlettes !!! (smaller size) but thats ok if your watching your waist line !!! (lol) Thanks again for a clean room and great superb service all the way around !!!

This is everything you’d want in a bed and breakfast! It’s a cozy country house complete with a fireplace and lounging cat right when you walk in. Our room (one of the cheaper ones) was comfortable, spacious and with a lot of natural light. There were beams from the old building, which gave it a neat feel. There was free wi-​fi and a delicious breakfast… What more do you need? We only stayed one night, but couldn’t be happier with our stay!

A single night’s stay was enough to lure us back for many nights in the future. Chesterfield Inn is both comfortable and romantic, and is designed with primarily couples in mind, with pet-​friendly thrown in as a bonus.
Our stay in Room 20 of the Wetherby building could not have been more pleasant and if all the rooms in the inn are appointed as nicely as this one then you can’t miss with room selection, though we’d advise you to get this one if you can. (It is listed as one of their top rooms so you’ll pay a bit extra.) Separate entry ways and windows with views of the woods permit privacy, though one is only steps away from the main building. Be sure to enjoy their wonderful (and gratis) cooked breakfast either in the inn or, even better, served on your private and spacious deck. In winter, make use of the gas fire place. In all seasons take advantage of the whirlpool tub and huge shower. If you want to check in with the world you’re trying to forget, then connect with free wifi. Dinners are served in the candlelit dining room.
Service is polite, friendly and efficient. Rates are typical for well-​appointed inns of this caliber and you will not feel cheated out of your expense. The inn is conveniently located just a few minutes from I-​91, and makes for a much more pleasant place to overnight than the hotel row on Route 5 in Brattleboro, and at some times of the year might be cheaper! Be sure to book ahead for busiest weekends.
We can’t imagine how this place could disappoint.

I only got to stay here 1 night, which is a pity, since this is a charming, relaxing place.
The rooms are spacious, and tastefully furnished. The service is friendly and attentive, and the food is great. There are comfortable sitting areas inside and out. TV reception and availability of channels is somewhat limited.
There is free wi-​fi (YAY!) but the use of that wi-​fi temporarily inserts a Meraki toolbar onto the computer screen. It shows various articles that you can read. The toolbar is not installed permanently, but is not removable as long as you use the wi-​fi. (Using Firefox browser with its add blocker does block it.) I found it distracting, and the idea is creepy, because it seems invasive of my privacy. If not for this, I would give 5 stars.

My husband and I got married on NYE and were looking for a quick getaway before he had to go back to work as a teacher. The Chesterfield Inn came highly recommended by several couples so we booked for a long 4 day weekend. From the moment we arrived we felt at home. Our room was spacious complete with a gas fireplace. The bed and linens were extremely cozy for a winter getaway. We peeked into a few of the other rooms which all have a nice homey feel. The grounds were gorgeous with the snow and I have a wonderful picture of the barn with christmas lights on my fridge.
The food was delicious and I am still craving their pancakes! Dinners were phenomenal from start to finish. The staff always smiled and we were congratulated left and right on our new marriage. The owners even had chocolate covered strawberries in our room after meeting them.
Needless to say we are already looking forward to another long weekend up there… and some more pancakes!

Swank indeed. We are talking country swank, of course. The Chesterfield Inn is part of an association of about 12 inns that call themselves DINE (Distinctive Inns of New England).
Unfortunately having booked late in the season, we ended up staying at the Hampton down the street — not-​so-​swank — but we were able to have dinner at The Chesterfield.
When we arrived, the hostess informed us that the staff was a little overburdened and asked if we would mind having a drink in the living room. We sat in front of the fireplace sipping wine for 15 min or so, before we were seated on a closed-​in porch at the back of the dining room. Over the course of our meal, other guests left and we found ourselves alone on the porch. We were the last in the restaurant, but our waitress told us not to rush, «I love seeing young people have the porch to themselves.» Awww, ok I admit it sounds a little nauseating, but he food was not. We started with wild boar and elk sausages served over a candied cabbage, followed by a wonderful fresh local salad. I had a bison ny strip steak, and my boyfriend had duck. Everything was wonderful. Finished off with a pumpkin bread, bread pudding.

I’ve stayed in a few B&Bs in my time and this is my favorite. I haven’t been in a few years, but per the website it doesn’t look like it’s changed much! The rooms are gorgeous and exactly what they advertise with cozy beds and nice, clean bathrooms. The restaurant here is amazing as well! This is actually where I had my first lesson on pairing wines with food. Dinner and breakfast are both amazing and the owners couldn’t be nicer! If you are looking for a cozy getaway with someone special… this should be on your list!