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    Canterbury Farm - Breakfast and Lunch

    Canterbury Farm

    (4 reviews)

    Wow! The couple who run this place are the warmest , helpful people!…read more The grooming was perfect and the conditions were fabulous. We meandered through well labeled trails and enjoyed the spectacular pathways of beauty. Yes, covid masks are required in the prep area and the number of skiers is limited. This place is so well managed and one of the most beautiful spots in the Berkshires. I am on my way back to try the snow shoe trails!!

    This review is for the cross country ski trails. Because I live in CT, where we have had very…read morelittle snow this winter, Canterbury is one of the closest places my son and I can go to ski. It is a little gem in the Berkshires, with a nice network of well-marked, well-maintained trails, and enough topographic and scenic diversity to give a good workout in a pretty New England forest. The prices are very reasonable, and equipment is available for sale or rent. Bathroom facilities are available in the house, and the B&B dining room is a nice place to take a break between runs on a cold day or settle in for a snack and a cup of hot cocoa before going home. The proprietors, Linda and Dave, are very hospitable, as B&B hosts tend to be. Condition reports are posted on their website, and I have found them to be accurate. My son and I have been there several times, and it is one of our favorite places, well worth the trip for us to get in a fun day of skiing at a nice place with friendly, welcoming hosts.

    Gedney Farm

    Gedney Farm

    (51 reviews)

    $$$

    I want to say it's more like 3 1/2 stars. But because the staff was so friendly and helpful I'm…read moregoing to give it the full four stars. I will give you all the pros first, then the cons. Pros: charming, rustic, lovely countryside location, food and restaurant looks good. (However we did not eat at the restaurant) it was pricey, probably as expected. The bed was very comfortable, the bathroom is large, the toiletries are very nice, housekeeping is great. They come in daily and made the bed and changed the towels and replenished toiletries. There is plenty of parking, it is close to Great Barrington, Lenox, Lee, Stockbridge, and yet slightly out of the way into the country, which makes it a special getaway. There are no televisions. Some may consider that a con, I do not. The property and buildings are beautiful. The reconverted barn made into the lodging area was done tastefully, and in keeping with the rustic charm it retained. Some of the rooms have fireplaces, great for the winter I suppose, there is a slight smell of smoke in the room. I like that, some may not. Contactless check in and check out are fine. I don't see the need for this anymore, but it is not a negative. Our room was unlocked and all ready when we arrived. Small caveat; our door did not fully close and was unable to be locked , we did find someone at reception who changed our room immediately. They even offered us an upgrade for no charge, but we decided to stay on the first floor, so as not to haul our luggage upstairs. There is a large glass water dispenser refilled every day in the hallway, along with a Keurig coffee machine, which includes many different pods, including decaf, also a tea selection. There are two small refrigerators in the hallway. I took advantage and left a bottle of milk in there for my morning coffee. It was very quiet, we did not hear any other guests, just some footsteps in the hall sometimes. The air conditioning cranked, which was great because it was a very hot weekend. Cons: there is rarely anyone at reception to assist if you need it. They rarely answer their telephone if you have a question. They rarely answer their emails if you have a question or concern. I made our reservation on line, no problem. I did call and email requesting an additional night to be added. It took 24 hours for a response, but they were able to accommodate us. Would have been nicer to know a little sooner however. I then emailed to ask if an iron and ironing board could be left in our room when we arrived and I received no response. The iron and ironing board were not in our room when we arrived. I did find housekeeping and they were happy to help me I remember calling between five and seven times on the phone before our arrival between 3 PM and 7 PM and no one answered the phone anytime. They do have breakfast from 8 to 10 in the morning, which is too early for me. Maybe not for some. A bland selection of muffins, no other bread items or croissants or rolls. Some nice cut up fresh fruit. Coffee but no decaf. I did not partake and did not think it was anything special. All in all, my husband said he would not return nor would he recommend this B&B to anyone, however, it certainly suited our needs, we were comfortable. At the end of the day was it worth $1000 for three nights? Probably not .

    My son and his bride had their wedding at Gedney Farm in June of this year. Everything was perfect…read more We checked in on Friday and checked out on Sunday and were taken care of by the staff the entire weekend. The ceremony and reception was everything they dreamed of! The food was terrific and the staff were spectacular! I only wish the day hadn't gone by so fast! It was a truly magical day!!

    Naumkeag House - Naumkeag - 9/1/2025

    Naumkeag House

    (37 reviews)

    The Winter Lights show is AMAZING! So creative, great use of all the uniqueness of the property…read more Very well organized. You park in the center of the town of Stockbridge MA which looks straight out of a Christmas romance hallmark movie. Even the town information booth (where you get the shuttle buses- which are school buses) over to Naumkeag House (less than 5 minute ride) looks like the cutest information booth you've ever seen. The buses are heated so after walking around outdoors you're happy to be on the warm bus ride back to the centers of the town. The light show has many nooks and crannies and surprises around every corner. I've been to much larger holiday light shows, and despite the size of this one being a bit smaller than some, it is spectacular and unique in so many ways. The property has a Chinese garden, a beautiful greenhouse (like straight out of frosty the snowman), a beautiful fountain, very large rows of giant evergreen shrubs, and incredible trees (like an arboretum). There are two "snack shacks" where you can get desserts, hot cocoa, hot cider, and even some nice add-ins like peppermint schnapps, bourbon, rum. Walking around looking at beautiful Christmas lights with a spiked hot beverage is magical. One of the snack shacks also has a fire pit with benches all around to sit and warm up by. Perhaps my favorite part...I went with several teens & young adults who don't always appreciate me taking tons of photos...but here...there were SO MANY PHOTO OPS that they didn't mind, and even started asking me to take more photos of them! Fair warning- this property has quite a few steps, so if mobility is a challenge, probably not the best place...even wheel chair accessible would be tough...especially with the school bus shuttles to/from town. Best to call ahead and see what accommodations can be made for accessibility. I hope to come back every year for the winter lights show. A very festive and beautiful thing to do with friends and family around the holidays.

    Another really underrated museum and estate in the Berkshires, the gardens and grounds are amazing…read more You have a wonderful view of the valley below and the house has a lot of stately charm. The tour guide we had was fantastic and is probably one of the best ones I've had for a museum tour. He was informative but kept it light. I didn't feel like he was flooding the zone with information to flex. There's some Asian/Chinese flavor in the home and the surrounding gardens, as the Choates had a keen interest in Asia. There's significant walking up and down, so keep that in mind, and not a ton of parking. This summer cottage is worth a visit, especially if you're interested in estates during the Gilded Age.

    Winbrooke - venues - Updated May 2026

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