Name: Chesterfield Inn
Address: 20 Cross Roadd West, West Chesterfield, 03466, US

10/10

Exceptional

29 Jun 2026

Beverly

Our stay at the Chesterfield Inn was absolutely wonderful. The inn is sweet, charming, and full of character. We slept so good and our room was so peaceful. We were treated to a beautiful sunset, enjoyed a delicious breakfast next morning, and appreciated the warm hospitality throughout our stay. The staff was exceptionally kind, welcoming, and helpful, making us feel right at home. We would definitely stay here again and highly recommend it to anyone looking for a relaxing New England getaway.

Partner

10/10

Exceptional

18 Jun 2025

Susan

This is a genuine five star property, an ideal of what a country inn should be. Beautifully designed and decorated, comfortable and welcoming, charming staff. One of the nicest places we’ve ever stayed.

Leisure Partner

10/10

Exceptional

14 Jun 2025

Wayne

Great stay

8/10

Excellent

07 Jun 2024

H

Lots of things were lovely; fantastic room service food (unbelievably fresh and delicious, better than anywhere I’ve ever eaten in a hotel while traveling), beautiful serene natural setting, and wonderful design of the buildings plus COOKIES and tea in the afternoon. The service was also fantastic. The paint could use freshening and the bathroom grout needs redoing (or consider retiling). A piece of one window pane, a wood bit, fell off… so I stuck it back, obviously needs a proper repair. With minor refurbishment, this establishment could be exquisite. Also, New Hampshire or Vermont local bath products would be preferable to English imports. Other things that made this a lovely place to visit was Yoda the tuxedo cat, the reclaimed barn main building, the lovely fireplaces, the proximity to Brattleboro and Keene, the pond and surrounding area, and the very amiable and kind, friendly staff.

Business_and_leisure Self

10/10

Exceptional

07 Apr 2024

Elise

A true find!

10/10

Exceptional

12 Jul 2023

Alicia

A must!

The perfect, charming bed and breakfast! Service was top notch from check in to restaurant service. The rooms are so comfortable and well decorated. We loved our stay here.

Friends_and_family Family

8/10

Excellent

12 Nov 2022

olivia

The location was very convenient for our purposes. Additionally the staff was very welcoming and accommodating. The breakfast as well prepared and tasty. We found the appointments and furnishings throughout but especially in the room, to be dated and tired. Given the price point for the accommodations, the value was lacking.

Leisure Partner

10/10

Exceptional

08 Sep 2022

Patricia

The place is beautiful, inside and out, the staff super friendly and attentive. Close to so many things, lovely grounds, lovely tea and delicious coookies delivered to room at night! Oh and breakfast on the porch is delightful too!

Leisure Partner

10/10

Exceptional

07 Jul 2022

John

Charming place with friendly staff and owners.

Leisure Partner

10/10

Exceptional

08 Jun 2022

Brandt

Great breakfasts

Leisure Partner

10/10

Exceptional

27 Aug 2021

Jonathan

Lovely near Bradenton.

Lovely inn. Served full breakfast in our room. Restaurant is superb and innkeepers welcoming

Partner

10/10

Exceptional

01 Jan 2021

Jeannie

Really very nice

Diana is really very nice, the staff was friendly and everything was well maintained. One issue for us was that as vegans there were not a lot of food choices, but takeout food from a nearby place did the trick. Would definitely return, thank you!

Friends_and_family Family

10/10

Exceptional

21 Sep 2020

Susan

A slice of heaven

We had a 2 night stay that was exceptional. The staff was friendly and accommodating. The food and wine list were phenomenal. We were able to eat dinner on the patio with the stars shining down on us. It is a place that you can go to to get away from the stress of daily living and be reflective and thankful for all you have.

Partner

10/10

Exceptional

19 Sep 2020

Allana F.

It was great. Peaceful, clean and food was amazing.

We came just for a night and loved it. The place was clean and cozy. The food was amazing. They even made us a gluten free breakfast which is so great! Thank you so much 💜

10/10

Exceptional

24 Sep 2019

JohnM

We stayed at the Chesterfield Inn for only one night but our stay was very pleasant. We received a friendly welcome at the front desk, our room was clean, bright and very comfortable. We had both dinner and breakfast at the Inn and both were veery good. The only down side is a bit of road noise but then we shut the windows and all was good.

Business_and_leisure Family

10/10

Exceptional

18 Jan 2019

Michele

Fabulous Inn. Quiet location, with amazing personal service. Excellent breakfast & dinner

Partner

8/10

Excellent

07 Oct 2018

POLLY

The Cat at Chesterfield

The Chesterfield Inn was very nice, not amazing but comfortable and a nice breakfast.
We got there late and left early so not much interaction time.
Close to Brattleboro and a wonderful restaurant DUO. Front desk was very helpful

Partner

10/10

Exceptional

15 Sep 2018

Verified traveler

Great breakfast in the dining room! Order off the menu. This gives you a real feel for a country inn!

10/10

Exceptional

17 Aug 2018

Verified traveler

Excellent Place to Stay

Our favorite B&B ever. Service, cleanliness, staff were all excellent. Don’t miss this one!

Partner

10/10

Exceptional

02 Aug 2018

Verified traveler

Better than Spa hotel. Just nice to relax!!

I was treated so well! one of the best hotels it ever stayed in . I stayed alone without a partner...got double the attention ...and extra care ;)
I would definitely recommend this to anyone who just wants some me time....alone time. A perfect romantic getaway but also the perfect solo TLC treat!! So sorry I felt so recharged !!

10/10

Exceptional

17 May 2018

Mark

Exceptional--probably the best lodging in the area

We have been making overnight trips to the Keene, NH – Brattleboro, VT area for over ten years, typically staying at a chain hotel and occasionally at a bed and breakfast. This week we tried the Chesterfield Inn for the first time. The large room, the comfortable bed, an outstanding breakfast, impressive views (from our room and the dining room), and the cordial and helpful staff all contributed to an exceptionally pleasant experience.

The range of options at breakfast is impressive. We both enjoyed the veggie scrambler, and the cranberry-gingerbread muffins were a delight. The inn also offers dinner in the dining room, and we might try it next time.

Why we had not tried the Chesterfield Inn earlier is puzzling. It’s almost right on the highway between Brattleboro and Keene, but easy to miss if you are not looking for it. And it’s not much more expensive than lesser hostelries in the area. We’ll be back.

Partner

10/10

Exceptional

07 May 2018

Diana

Beautiful rooms and excellent service. Food was exceptional.

10/10

Exceptional

18 Apr 2018

David

Better late than never

This was the first-time we have ever stayed at a bed & breakfast. We may never stay at a hotel again! The staff couldn’t have been nicer. The meals (we had dinner and breakfast there) were outstanding. The room was huge, the bed comfortable and the fireplace just added to the overall ambience of the place. If you’re looking for a great getaway, look no further! We can’t wait to go back!

Partner

10/10

Exceptional

30 Mar 2018

JEAN

Home away from Home

We have stayed here a number of times. The rooms are spacious and very comfortable. The breakfast is not to be missed. It is excellent! The area is especially wonderful during the Fall foliage season.. There are a number of good restaurants near by. There are also many activities to enjoy i.e. hiking, biking, kayaking, canoeing, museums, and of course retail therapy.

Family

10/10

Exceptional

06 Jul 2015

Verified traveler

Beautiful Inn

We stayed two nights at beautiful Chesterfield Inn in June and we were charmed. Our room was spacious, very well decorated and perfectly clean.

The staff was courteous, helpful and friendly.

We dined twice in the bright and airy dining room and enjoyed both dinners.

Finally, we found that the Inn was a perfect location from wich to visit the Clark Art Institute and the MASS MoCA.

Philippe T.

Quebec City

10/10

Exceptional

06 Jul 2015

Verified traveler

Beautiful Inn

We stayed two nights at beautiful Chesterfield Inn in June and we were charmed. Our room was spacious, very well decorated and perfectly clean.

The staff was courteous, helpful and friendly.

We dined twice in the bright and airy dining room and enjoyed both dinners.

Finally, we found that the Inn was a perfect location from wich to visit the Clark Art Institute and the MASS MoCA.

Philippe

Quebec City

8/10

Excellent

09 Jun 2015

Verified traveler

Cozy cottage inn

Highly recommended if you are visiting that part of Vermont and looking for a quiet, cozy, and stylish inn. It's got all the comfort amenities you'd need. We especially like the ambience early in the morning at the restaurant at breakfast time, as the view of the hills and garden in the back provides a soothing way to start your day. The ambience is also matched by a great breakfast (included) --- they usually have a selection of specials each morning. We've been staying here the past 3 summers when we drop off our daughter at boarding school in northern MA; although its a 20 minute drive, its a great place to come back to and relax at the end of the day.

8/10

Excellent

23 Oct 2013

Verified traveler

second visit

Again, our stay at Chesterfield Inn was great. The rooms were comfortable and generous. The food at the Inn was outstanding! Made to order breakfast was delightful and dinner was the best! This was a highlight for our New England vacation.

10/10

Exceptional

17 Jul 2013

Verified traveler

Sweet

Our stay was very pleasant. Our room and bed were comfortable and clean. The food was outstanding. We will stay again when we come back this way. Great value.

6/10

Pleasant

24 Feb 2013

Verified traveler

Pleasant enough

Room was pleasant but plain. Dated. Could benefit from a small microwave. Food is nothing special and they cannot cater to special dietary needs. Website shows a much embellished version of reality.

10/10

Exceptional

11 Sep 2012

Verified traveler

Great!

Pleasant, well-run, clean -- good food, charming staff.

8/10

Excellent

14 Aug 2012

Verified traveler

R&R

What a beautiful property! Chesterfield Inn was relaxing and refreshing. Food in restaurant was excellent!

10/10

Exceptional

14 Aug 2012

Verified traveler

Quick Getaway

The Chesterfield Inn was delightful! Our quick getaway was so relaxing -- our room was tastefully decorated, included thoughtful amenities, and was peaceful with views overlooking the pond. Dinner on the patio was fabulous!

10/10

Exceptional

07 May 2012

Verified traveler

Peace & Quiet

We enjoyed our stay at the Chesterfield Inn. it was a perfect place for peace and quiet -- just what we needed at this time. The staff was gracious, the room, immaculate, and the food superb. We highly recommend it.

10/10

Exceptional

22 Apr 2012

Verified traveler

A perfect getaway!

We needed to escape our life and Chesterfield Inn provided the perfect setting. We highly recommend rm 20. It has a great view, private balcony, gas fire place and jacuzzi tub. The mini fridge was even stocked with an assortment of beverages. The food is phenomenal. We consider ourselves foodies and have enjoyed meals in some of the best restaurants. The cuisine here rates right up there and they have some wonderful wines. The Inn is within east driving distance to Keene and Brattleboro.

10/10

Exceptional

18 Apr 2012

Verified traveler

A True Gem

The Chesterfield Inn is a restful, relaxing haven -- like a home away from home! Delicious food, luxurious accommodations, wonderful, friendly service. A true gem!

10/10

Exceptional

12 Feb 2012

Verified traveler

Excellent stay

We loved it here! Great beds! Great staff!

8/10

Excellent

12 Feb 2012

Verified traveler

A Grand Experience

Everything was beyond expectations. The service and food were excellent and staff were exceptional.

10/10

Exceptional

04 Dec 2011

Verified traveler

Best B&B

I loved this place. Adorable rooms, plenty of space. Wonderfully decorated. Wonderful food. Great staff!

10/10

Exceptional

31 Oct 2011

Verified traveler

Best Bed & Breakfast

The people were so kind, great atmosphere, private room and deck, loved it!

8/10

Excellent

06 Aug 2011

Verified traveler

We loved it and we'll be back!!!

We were so happy to find a beautiful inn that is pet friendly! Our pooch enjoyed it as much as we did!! Lovely accommodations, great staff, GREAT food!!

6/10

Pleasant

06 Aug 2011

Verified traveler

Family Getaway

We had a lovely three days at Chesterfield Inn. The place was quaint and quiet. The staff were exceptionally friendly and helpful and the food was superior!

8/10

Excellent

02 Aug 2011

Verified traveler

So peaceful and relaxing

I was looking for a nice, quiet weekend away for my fiance's birthday and I got it! The Chesterfield Inn allows you to just sit back and enjoy your time and you don't have to do any work. The staff goes above and beyond making you feel more than at home. It was lovely!

10/10

Exceptional

07 Jul 2011

Verified traveler

A great romantic gateway

My husband and I spent a weekend at the Chesterfield Inn and it was lovely. All the members of the team gave us a warm welcome and were very helpful during our stay. We had an amazing and restful weekend in this wonderful bed and breakfast.

10/10

Exceptional

01 Jul 2011

Verified traveler

Outstanding Inn

We were very warmly greeted and personally shown to our room, number 11. we had a private balcony, rough hewn beams canopied over the bed and a fantastic bath. Breakfast was beautifully served and tasted fabulous. Our two night visit was relaxing, luxurious and more than we had hoped for or expected. We will make this B & B and yearly visit

8/10

Excellent

11 Jun 2011

Verified traveler

wonderful!

My mother and i stayed 2 nts at the Inn....wondered if the pics would live up to their statement----they did. The room was spacious, clean and comfortable...The food is great! Home made cookies with tea and a huge-did I say huge- breakfast.....something for everyone on the breakfast menu!

We would definitely come back.

10/10

Exceptional

02 May 2011

Verified traveler

Wonderful Weekend Getaway!

My boyfriend and I spent the night at the inn and it was a perfect get away! The rooms were immaculate, and the service was great. The breakfast was exceptional! Thank you for a lovely weekend!

--Elise, CT

10/10

Exceptional

21 Feb 2011

Verified traveler

Cozy B & B

A good place to have aweekend getaway. Only 3 1/2 hours from NJ or NYC. The rooms with fireplaces make for romantic ambience. From full breakfasts with special selctions, tea and homemade cookies in the afternoon, and fabulous dinners, you never have toleave the Inn. This makes for a relaxing weekend away from it all. THe stove by check in is warm and welcoming, the fireplace in the sitting area beckons you to have your tea and cookies there. You can even have cocktails before dinner in the sitting area if you wish. A special place for rest & relaxation or a romantic getaway. Even a horse drawn sleigh ride recommendation to assist you to enjoy your special time can be requested. The staff is friendly and go out of their way to assist you when needed without intruding on your time. A wonderful place to stay and gets repeats from us.

10/10

Exceptional

20 Feb 2011

Verified traveler

Chesterfield Inn Is A Gem

We had our first visit to the Chesterfield Inn this weekend, getting the massage package and couldn't be more pleased. Everything was perfect and my wife couldn't have been happier with my choice for an inn.

Have dinner there, it's well worth it! Great breakfast, too. Super clean and all the staff couldn't have been more personable or pleasant. Close to Brattleboro for shopping and walking around, yet a very quiet location just off route 9. Can't wait to go back.

10/10

Exceptional

14 Dec 2010

Verified traveler

Great Service

Cheerful and helpful staff along with the ambience of authentic architecture of New Hampshire

made our experience very pleasant. A full breakfast is included and the dining room has a lovely vista. Best of all, the room was quiet even with proximity to roads.