We stayed at the Chambery Inn this weekend. It was beautifully maintained, clean, a great location,…read moreeasy/contactless check in and check out. We were asked our wine preference and a delicious bottle of red wine was waiting for us. It was also great to see some of the pieces of the schools history maintained and fun reading all the notes left on the chalk boards by previous guests. There was keurig machine in our room and outside in the hallway as well as an espresso machine, both fully stocked with lots of great options! We happened to be there over Memorial Day weekend so had a nice view of the parade sitting right outside of the Inn! We will definitely be back!

Wow!!! This place is literally a gem! I'd give 10* if I could. Vibrant, cozy, historic, clean,…read moreperfectly maintained in every single detail! Olia the owner such a sweetheart!Recommended favourite places to eat and be entertained, so many things to do there. It was our first experience in Berkshires but definitely not last, can't wait to come back! I travel a lot in US and abroad, and trust me - you'll love that place from the very first step in! Is quite convenient to be in the middle of the town, the hotel's parking is pretty spacious! We loved our humongous room with beautiful interior, a fireplace. Also we bought a homemade maple syrup, the taste is yummm!

From arrival to departure we felt well taken care of. Welcoming cocktail, after dinner cognacs and…read moredelicious brownies were complimentary and very much appreciated! Our room was small but accurately described on the website. It was tastefully set up and it had a view of the lake which was beautiful. The breakfasts were very nice with several choices and nice table service. Also, the location is excellent. Besides being on the lake it is within minutes of many Berkshire attractions.

We had a wonderful two night stay. Inn is lovely and on a beautiful lake with kayaks and outdoor…read moreseating. So relaxing. The daily breakfast was delicious! Also enjoyed the afternoon sangria and evening cognac tasting. This place is a gem and we will definitely be returning! Thanks Kurt for a wonderful inn!

AppleGate Inn B&B in the Berkshires is so awesome. We found it just they Google, I booked the place…read moreFriday afternoon and we drove up. Arrived late and went right to our room which was so perfect, everything clean and even Rum! (We aren't pirates so we didn't drink the rum). On Saturday morning we come downstairs and there's the best breakfast we ever had with classical music and elegant dining room and just everything perfect. There's a piano here and the bathrooms are spotless and we love it. Walking around town of Lee and the Berkshires today and very happy! Thank you AppleGate Inn!

My wife and I just came from there and we had a nice stay. I liked the town of Lee and the Inn is…read morein a good spot to get where you are going. They provided Breakfast each day that was just Ok. The staff was nice. The Room was nice , the bed was comfy and we loved the fireplace. I would stay there again.

Fantastic bed and breakfast in the middle of the bucolic Berkshires - a fantastic escape for a…read moreromantic sojourn or simply a peaceful retreat. Doug and Jim go above and beyond with their hospitality always with a smile and friendly gesture. Jim's breakfast desserts are phenomenal and the Happy Hour with live music is superb with Doug and Jim both lending their voices to entertain guests in collaboration with a pianist that truly brings back the concept of Parlor music into the 21st century. The musical ambiance at breakfast is also reminiscent of my own playlists, with a mix of classical, new age, and soft instrumental listening. The historic inn retains much of its charm with original details throughout - truly a step into New England country charm. My partner, now fiancée, and I thoroughly enjoyed our stay and it will forever be memorable as our engagement destination. We are looking forward to returning for many years to come!

Our recent stay at the Devonfield Inn was our first and will certainly not be our last!! The Inn is…read morebeautiful, well appointed and is located in the amazing Berkshires. The Inn Keepers, Doug & Jim were gracious, informative and attentive! Our suite was very welcoming, comfortable & clean! We enjoyed true comfort during our stay. Breakfast was really good each morning with great selections of savory & sweet offerings. The Inn's location is central to many restaurants @ attractions which made day trip's really easy. A very special Inn indeed!!

All it's a great place in the owners are very nice. It's a beautiful room with everything you can…read morepossibly imagine to need.

We had a wonderful weekend at the Inn at Stockbridge. The room (Greek Isles) was very spacious,…read moreclean, and comfortable. It was nice to have the outdoor space to sit in. The breakfast was good but the afternoon cookies even better. Snacks and drinks were always available. Best yet was the location-minutes from Stockbridge, Lenox, and Great Barrington. The staff was wonderful-even found our iPad and ships it back to us. Certainly a great stay if you're going to be in the Berkshires!

You won't find many places like Conroy's,in the Berkshires or elsewhere for that matter. From the…read morewarm home like surroundings, to the ample grounds to wander, and a swimming pool (summer only of course!), to Joanne's knowledgable suggestions, there's no finer B and B in the Berkshires. The personal one to one connection that she brings to the stay is priceless. My wife and I came here on the recommendation of local friends many years ago, and have been returning several times a year for years.Btw, Joanne's breakfasts are really truly splendid-they put the "breakfast" back into thedefinition of bed and "breakfast"!

A lovely B & B with 9 antique rooms, beautiful, scenic grounds and a swimming pool in season. The…read morelocation is only a mile from downtown, historic Stockbridge and equally as close to Lee, MA. Ultra clean rooms, beautiful gathering places with interesting artwork, games and comfy chairs and couches. All good. The owners, Joanne and Jim Conroy, could not have been more welcoming, arranging the Rose Room with an extra cot for my youngest daughter and serving us an absolutely delicious breakfast each day. We feasted on fresh fruit and orange juice, coffee/tea, yogurt with granola and home made nut pancakes, quiche, and just out of the oven muffins. The conversation with various guests from countries like Belgium and Germany was wonderful. A rolling outdoor lawn was a fabulous spot for a picnic lunch. All in all, we can't wait to come again to visit local favorites such as Naumkeag, The Divine Mercy Chaplet, Tanglewood, The Rockwell Museum, and so much more. An all season destination, come to Conroys, hands down better than any hotel! Five star!

This place has MANY problems! Check the public records for yourself, as reported by the local…read moreBerkshire Edge news source (June 12, 2026): "Lee Police Department reports for The Pilgrim Inn from January 2025 to June 8, 2026 = 82 calls were made from the hotel during that time, including follow-up investigations, averaging one call about every 6.3 days. Although some of those calls cite more than one type of incident, the statistics include 14 medical emergencies, 13 well-being checks, seven "unwanted party" calls, seven "threats," six domestic issue calls, and four restraining orders." "TriTown Health Department records for The Pilgrim Inn from 2025/26 = double-digit sanitary code violations and complaints. Those violations included sewage backup, inadequate ventilation, soiled mattresses and torn sheets, unsanitary tub conditions, stagnant water in a half-empty swimming pool, standing water in the basement, evidence of rodents, bedbug complaints, non-functioning smoke detectors, and unfit conditions that posed a health or safety risk to the hotel's occupants. Many of those violations required guests to immediately vacate the room and owners to make corrections within 24 hours. On reinspection of those violations, inspectors noted numerous times that the issues were not remedied." There are MANY better choices for lodging in the Berkshires...

This place uses fraudulent ways to cancel & book for higher rates. I had a reservation for a month…read more& 2 days before they canceled on me for no reason. They claim I canceled through Expedia. Expedia says it was canceled via a website. I knew nothing until receiving an email about the cancellation. When I asked the hotel to rebook they said they were full. This was a half hour after the cancellation notice. I'm sure they booked it for more money. This is an awful way to do business.

I stayed here for two nights with my partner and our two small dogs…read more We just wanted to check out the Berkshires for a day or so, nothing crazy. This seemed like a very reasonable compromise in quality and price. There is nothing immediately within walking distance regarding restaurants unless you consider the restaurant in the hotel. This place, however, is on the road in between Lee and Lenox so is pretty convenient with a car, many places within 5-10 min drive. The lake views are gorge, especially if you are lucky enough to get a room overlooking it. Our view was of the parking lot but I can't complain given how much it cost per night. The room wasn't overwhelmingly large but we had enough room to open our suitcases, so that was nice. The bathroom was decently sized. The staff I interacted with were all very nice and friendly. I had to sign away the possibility of seeing another penny in my life if my dogs had any kind of accidents but fortunately they were well behaved. I am not sure if there is an elevator btw which came as a surprise. Fortunately this was just a two night stay (which doesn't guarantee anything with me) so I was able to carry my shit up the stairs pretty easily. I thought the bed was comfortable and they provided more pillow than I am used to. The thermostat worked well. There wasn't a closet or iron probably the first time I've ever needed to use one. I would stay here again.

Extremely friendly staff upon arrival. The furniture was…read moredefinitely outdated, but it didn't take away from the comfort in the room clean spacious bathroom. Everybody on here is complaining about the breakfast food, but to be frankly honest with you I don't know what people expect when it's for free. No it's not a gourmet meal, but a slice of toast and a hot cup of coffee is enough for me. And definitely people were grabbing everything. I'm definitely stay here again. Yes, I heard the man upstairs walking all night long but you can't fault. An old hotel for that. If you're looking for a really decent place to stay for a really decent price this is your place.