Bed and breakfast holiday rentals in Berkshire County

George and Annalee are wonderful hosts. From their insight of local recommendations to the thoughtful ways they make sure you feel right at home, they really exemplify what Airbnb was created to be. Ordinary civilians like you and me who love meeting people from all over the world. They are there to great you upon arrival and to make sure you know your way around the house. I would recommend commuting in/out with a car, because the location is quite remote and not walkable especially with luggage. It’s the perfect place to retreat and disconnect.

We had such a lovely time staying at George and Annalee’s! The breakfast was excellent, including catering for us being vegan, and they gave us great local recommendations. They were really hospitable and friendly including picking us up from the bus stop in town! We really enjoyed our stay and would definitely stay there again.

Dalija was an incredible host. she was there to greet me right at check in and gave me the run down of the airbnb room and the surrounding area. she was very responsive and her place was very homely and accommodated all my needs perfectly. if Im ever in the area again I would definitely rent one of her rooms!

Super charming home and guest space upstairs. We were looking for a comfy place to spend a few winter days with our Williams student and this fit the bill perfectly. Super close to campus, but the view out of the northwest window made it feel like we were in a wood cabin in the middle of the woods somewhere. Great communication with owner.

Another great stay with Josie and Scott! Close to the center of town, and close to so many sights and activities. The suite itself is lovely and homey, the bed is super comfy, Josie and Scott always make us feel welcome, and kitties are an added bonus.

A perfect stay! Everything was wonderful, and I would love to stay again. Warm common area with comfy furnishings and a fireplace with an outstanding library! Rooms are so thoughtfully designed! Lovely Beekman Bros. Toiletries, Extending magnifying mirror in bathroom, comfy bedding, and a delicious breakfast made for a wonderful stay. Have already recommended to family and friends.

The Sheffield was great! From check in to check out! Susan was the best hostess! Even with my hectic schedule with an early rise, she was always there to greet me with a smile and a hot to go coffee. Was so very kind and welcoming to my dogs! We’ll definitely be returning next time we have a sheepdog trial in the area! 😊

A beautiful location tucked away from the road. Susan clearly enjoys what she does and goes above and beyond to accommodate—plus spoiling us with a lavish breakfast every morning!

This is a beautiful historic inn, full of grace and interesting furniture and art. The woodwork and fixtures are lovely and well-restored. We enjoyed the breakfast, which was beautifully prepared and shared in a very large, well-appointed dining room. Conversation was very nice with other guests, and with the owners, Richard and Joan, and their daughter Lisa, who is the main host. We had delightful conversations with each of them, along with great recommendations for area activities and restaurants.

Susan graciously accommodated us during the busy holiday season and her house was spacious enough for our group of two families with kids. The house is easy driving distance to Butternut for skiing as well as other spots in the Berkshires. Breakfasts were made from scratch and included multiple options. Susan was also kind enough to quickly reach out when we'd left behind an item of sentimental value—we really appreciated it.

Lisa was great! My girlfriend and I showed up a little later in the night and Lisa came down to greet us and help us check in to the room. Everything was gorgeous and the space was clean and comfortable.

The whistlers Inn in Lenox is a hidden gem with a beautiful library and parlor, lovely breakfast service, and a warm, friendly host in Lisa. The bed was super comfortable and we walked up into Kennedy Park and out on Parsons Marsh after I had settled my parents into assisted-living. I plan on reserving a room again there soon.

Great place to stay to enjoy Lenox and the Berkshires!

Josie and Scott are the best. They made me feel very welcomed. Coffee and banana bread plus other goodies were waiting for me in the morning. I will definitely stay there again; I am booked to stay there at the end of May