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    Conroy's B & B

    4.8 (8 reviews)
    Closed 9:00 am - 9:30 pm

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    The Red Lion Inn - Welcome to our table!

    The Red Lion Inn

    (471 reviews)

    $$$

    My wife and I ended up having lunch in Stockbridge after taking the day off together to celebrate…read moreour 36 wedding anniversary and we are so glad we did. We had wonderful lunch in the main dining room in the Red Lion Inn. Our waiter Matt was very nice! Unfortunately he had the whole dining room and things took time. Other than that we truly enjoyed our lunch. I had the Roast Beef sandwich special which was fantastic! One of the best I have ever had. Not sure it is worth $28 for a small sandwich though. My wife loved her Caprese Sandwich. I had Apple Pie with a scoop of vanilla ice cream which was good... not great. I'd skip it next time. Matt came with the coffee I ordered and said the pie was in the oven so when it finally came out I was expecting a very hot apple pie. That was not the case which was disappointing. Overall a wonderful experience and if we are ever in the area again, we would definitely stop for lunch again.

    The Red Lion Inn has so much history and character, it was a wonderful…read moreExperience to say the least. With modern amenities, it still Managed to keep its old world charm Food at the Wolf Den Tavern offered some of the best clam chowder I have ever had Enjoyed the hot tub but both hot tub and pool were difficult getting in and out of for someone with mobility issues like me Breakfast in the main dining room was also wonderful with very pleasant staff Upon check in, the only employee at the registration desk was on the phone with a customer for a good 15-20 minutes while the line behind me were all waiting to check in. Since check in time is 4:00, and we were there at 4:30 it seems like there should be more than one employee checking in customers Overall a wonderful stay. One that I would happily do again

    Stockbridge Country Inn - Dining area

    Stockbridge Country Inn

    (8 reviews)

    $$$

    Beautiful and cozy, and very clean. Diane is the most exceptional hostess, very accommodating and…read morelovely women

    If some Hollywood director called central casting for the perfect country inn, the Stockbridge…read moreCountry Inn would get the part. Envision a white country farmhouse, impeccably decorated with period furniture and wall paper, and featuring two sitting rooms, one with a southern exposure for lots of light, an ample dining room where you will be served an excellent and more than ample breakfast, and a den with a great wood stove and filled with hundreds of books about American history. Every bedroom features a private bathroom with the most modern appointments and plenty of hot water and soft towels. You'll also find toothbrushes, etc., in case you rushed out of your house just ahead of the SWAT team. The bedrooms are beautifully decorated and the furniture is of the highest quality. Your inn-keepers are Diane and Vern, warm and friendly, ready to oblige and make your visit a wonderful memory. We have stayed there twice in the past, and this time, the weekend after Presidents' weekend, we were the only guests and had the place pretty much to ourselves, so we got to spend lots of time with Diane and Vern. Here's an example of exceptional customer service: lots of snow was predicted for Friday, when we drove up. Diane called and gave us the option of simply cancelling if we didn't want to brave the weather. Of course, the snow materialized Saturday night, so we were glad we made the trip. One other note, the guest demographic is pretty high end - folks who could otherwise stay at Blantyre etc., but who want a more intimate experience. In our prior stays, the other guests were friendly and ready to engage in interesting discussion around the breakfast table. We'll be back next fall!

    Devonfield Inn

    Devonfield Inn

    (39 reviews)

    $$

    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!!

    Briarcliff Motel - The Modern room is comfy, clean, and cute.

    Briarcliff Motel

    (65 reviews)

    $$

    This place (THE LITTLE LION INN) is a joke. No one works here. The main office area is locked and…read morethere is no one on site. No coffee maker or vending machine or breakfast or any sort of place to hang out. It seems haunted or abandoned, and it's super badly maintained. Scratches and chipped paint, dirty floors, wrinkled up rugs, holes in the wall. Even the fire pit is "no longer working". I can't believe this is even a place that can be paid for by tourists. We also found a bug in our bed the first night and switched rooms. They were less than empathetic. There are also "locals" that stay here for long stretches under some sort of mental or physical welfare situation, so be aware if you choose to stay. There is some operation between this motel and the local law enforcement to put up people in need. There is also NO HOUSEKEEPING SERVICE. they don't service the room while you are staying!!! No fresh linens, no garbage clean up, no sheets changed, nothing. I can't believe that. I hope this place gets knocked down and rebuilt. What a joke. The only nice thing here was the new retro mini fridge. I could buy one of those for a nights stay, though. The new owners should be ashamed of themselves for renting this place in the condition it's in. It's not even fit for paying guests. Also... a 20 inch tv? In 2025? Come on. Barely any outlets in the room. No closets. Only some rooms have suitcase stands. There is also no coffee maker in the room so you can't make coffee, tea, or anything. One of the worst hotels I've ever been to.

    Have been staying at the Briarcliff for the past 5 years. The newly renamed, Little Lion" has…read morecertainly lost all sense of appeal. There is no longer an inn keeper on-site and as a result the main lobby is inaccessible. This includes any access to coffee or the delightful breakfast pastries that had been available during previous years. Additionally, the lack of on-site staff meant that as anyone arrived at the inn they were inquiring about the processes, reservations and room accesses. I didn't know that I would be paying for a weekend away only to be put to work as an innkeeper. Highly recommend staying elsewhere.

    The Black Swan Lee - Lenox, Ascend Hotel Collection - The breakfast nook

    The Black Swan Lee - Lenox, Ascend Hotel Collection

    (68 reviews)

    $$

    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.

    Conroy's B & B - hotels - Updated July 2026

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